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1-50 of 237 Chatham Rentals

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Overlooking Nantucket Sound and large lush lawns
1 / 8

Chatham Home
9 Bedrooms / 4 Bathrooms / Sleeps 20
Home / 9 Bedrooms / Sleeps 20

(3)“ Excellent ”3 Reviews

Bedrooms:9
Bathrooms:4
Sleeps:20
Type:Home
Per night:$1,250
Per month:$37,500
Pets allowed:No
Internet:Yes

Southwesterly ocean breezes flow over this HISTORIC family estate built in the 1930?s by Mr. & Mrs. John Peale Bishop, a classmate and best friends at Princeton of F. Scott Fitzgerald and himself a famous writer and poet. The Gatsby sits on 1. 3 acres in Chatham overlooking Nantucket...

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Tribute & fond memories

“ Excellent ”
October 7, 2014
This house was perfect for our needs. We needed a place which felt like our home at the Cape for so many summers. We had to all be under one roof, sharing stories, memories, laughs & tears. We came to the Cape to sprinkle my husband's ashes at sea. The house is large, spacious and clean! The furnishings served their purpose and the fireplace made for the perfect atmosphere. I was able to prepare a sit down dinner for 20, plenty of pots, etc. The two refrigerators made prepping and serving very easy.Tara cleaned the house prior to our arrival and Carver, her spouse and the Caretaker took care that our every need was met. Every member of my family was thrilled to have been able to spend the weekend at such a warm home for dad's final sendoff. The home owner introduced me to the Stage Harbor Marina and I was met by the kindest, gentlest man you'd hope to meet. On Sunday we returned to NY with a feeling of peace and the wonderful Gatsby made it possible, Thank you!
margaret brady, Hudson Valley, New York

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Chatham Massachusetts Vacation Rentals - Home
1 / 16

Chatham Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

(3)“ Excellent ”3 Reviews

from

$393

/ night

Email Owner
Bedrooms:4
Bathrooms:2.5
Sleeps:8
Type:Home
Per night:$393 - $643
Per week:$2,750 - $4,500
Pets allowed:No
Internet:Yes

Charming, updated sea captain's home in Old Village just off Main Street, with views of Little Mill Pond. Short walk to Lighthouse Beach, Friday night band concerts, shopping and restaurants. Beautifully furnished and appointed, surround- sound entertainment, gas fireplace, ...

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Great Summer Vacation 2014

“ Excellent ”
August 25, 2014
I spent a week at this delightful home with my husband, adult children and their spouses/significant others! There were 8 of us and plenty of room for all. Loads of kitchen and outdoor space. Walking to the village every day was easy and fun. (Ice cream every night and iced coffee each morning!) The beach was a quick walk. This home was very clean and updated! I would recommend it to anyone!
Andrea Rasmussen, Geneseo,NY

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Chatham Massachusetts Vacation Rentals - Apartment
1 / 4

Chatham Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

from

$193

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$193
Per week:$1,350
Pets allowed:No
Internet:Yes

Conveniently located South of Route 28 and less than a mile to popular Ridgevale Beach, this 2 bedroom, 2 bathroom Town House style condominium is absolutely pristine. The unit has been totally renovated with features including Pella sliders to the two decks, tiled bathrooms, ...

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Chatham Massachusetts Vacation Rentals - Home
1 / 14

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

(10)“ Excellent ”10 Reviews

from

$290

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$290 - $345
Per week:$1,800 - $2,700
Pets allowed:Yes
Internet:Yes

This charming Cape Cod style home is an attractively- furnished 6 room, 3 bedroom, 2 bath home that is only a 2 minute walk from the Pleasant Street Beach, for which a sticker is not required. It has a rooftop deck with a lovely view of Nantucket Sound and is only 3 miles from ...

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Cape rental

“ Excellent ”
September 11, 2011
Nice home, convenient to beach. Loved the upstairs deck.
Marti Barcelos, simsbury ct

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Chatham Massachusetts Vacation Rentals - Home
1 / 17

Chatham Home
4 Bedrooms / 2 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

Enjoy the spectacular location and panoramic waterviews from this 4 bedroom 2 bath Chatham rental cottage situated right on Cockle Cove Beach on Nantucket Sound. This is one of very few cottages where you can step out your door and take only a few steps to the water's edge. This property...

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Front View of Cranberry Way, South Chatham
1 / 11

Chatham Home
2 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

(12)“ Excellent ”12 Reviews

from

$175

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$175 - $215
Per week:$1,000 - $1,600
Pets allowed:Yes
Internet:Yes

This charming Cape Cod style cottage is a delight! It is a 2 bedroom, 2 bath home (one large new one) on a large lot with much privacy. It has A/C, hi- speed wireless internet, a new wide- screen HD TV, new carpeting throughout the house, is on a no- outlet street so it is safe...

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Ok property but equipment issues

“ Very Good ”
April 6, 2015
First we had issues with a lock although our lease said door would be open. Then the wifi didn't work, one of our CD's got stuck in the ancient CD player and the very old dishwasher has such a coating of old soap/salt that we felt we could not use it. Could do with a bedside lamp in twin bedroom. Unmade road to house with huge potholes. Otherwise the properly is good. Short drive to Cockle Beach.
Maureen Wooster, Natick MA

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Chatham Massachusetts Vacation Rentals - Home
1 / 11

Chatham Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Enjoy your vacation and be close to Nantucket Sound at this adorable 2 bedroom cottage only 3/10ths of a mile from Nantucket Sound beaches. This property has a portable A/C unit in the bedroom with Queen, washer/dryer, digital cable TV (includes NESN, ESPN, etc.. ), VCR and DVD,...

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1 / 10

Chatham Cottage
2 Bedrooms / 1 Bathroom / Sleeps 6
Cottage / 2 Bedrooms / Sleeps 6

(4)“ Excellent ”4 Reviews

from

$93

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Cottage
Per night:$93 - $165
Per week:$650 - $1,150
Pets allowed:No
Internet:Yes

$1150/week–High Season–lower other times Foote- steps Chatham Charmer - Weekly Rentals The charm of a Cape Cod cottage with all the amenities of home. Relaxation and conveniences on a private circle with idyllic nature views... Enjoy our enclosed porch overlooking the salt...

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Off Season

“ Excellent ”
September 26, 2013
We have rented this cottage multiple time. It is on a quiet street with a veiw of the salt marsh; a short walk from the beach. We love to watch the birds and dragon flies and relax.
Laurie Chadbourne, Amherst, MA USA

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1 / 37

Chatham Home
4 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 4 Bedrooms / Sleeps 6

from

$700

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:6
Type:Home
Per night:$700
Per week:$4,900
Pets allowed:No
Internet:Yes

180+ photo gallery available upon e- request. This exquisitely furnished four bedroom home is located on the Ocean side of Shore Road with an easy walk to Chatham's beaches, Fish Pier, Lighthouse, town center, outdoor band concerts and fine restaurants. Just minutes walk...

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Cape Cod Emery Pond
1 / 37

Chatham Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

(7)“ Excellent ”7 Reviews

from

$395

/ night

Email Owner
Bedrooms:4
Bathrooms:2.5
Sleeps:10
Type:Home
Per night:$395
Per month:$11,850
Pets allowed:No
Internet:Yes

ON THE WATER ... Beautiful water views! Back decks open to mesmerizing views of Emery Pond Hammock and patio furniture chosen for comfort and relaxation! Direct access to pond from backyard. Clean swimmable pond. Bass fishing plentiful! Gas grill. 2....

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Happy Family

“ Excellent ”
December 2, 2014
Took all the family to the Cape for a Family Thanksgiving. Eight of us stayed in the house and a baby, We had a super time and the housewas perfect for us. Great location. We had rain, snow and wind and sun. Owner was very easy to communicate with.
Edie Garrison, Needham, Ma and kids from all over the country.

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1 / 6

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(4)“ Excellent ”4 Reviews

from

$172

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$172 - $558
Per week:$1,200 - $3,900
Pets allowed:No
Internet:Yes

Cape cod home on the shores of South Chatham. The main floor constists of an eat in kitchen, living room / dining room with three picture windows, a brick fireplace, a four window reading room facing the ocean, and a full bathroom with an accessable shower. The upstairs sleeping...

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One To Remember!

“ Excellent ”
December 16, 2012
Older sibling reunion. The pictures don't capture the beauty of this property. Obviously plenty to do in this area. The owners were remarkable in their effort to meet our needs. The single resident seagull is charming. We will love to return!
Frank, Milford, CT.

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1 / 15

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$372

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$372
Per week:$2,600
Pets allowed:No
Internet:Yes

Swim, fish, bike or just plain relax at this private, comfortable retreat in Chatham. In a quiet, wooded setting, cooled by the breezes from the pond, and ceiling fans, the home's open floor plan is well suited for gathering. The first floor of this home includes the living...

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Chatham Massachusetts Vacation Rentals - Guesthouse
1 / 22

Chatham Guesthouse
3 Bedrooms / 3.5 Bathrooms / Sleeps 6
Guesthouse / 3 Bedrooms / Sleeps 6

(8)“ Excellent ”8 Reviews

Bedrooms:3
Bathrooms:3.5
Sleeps:6
Type:Guesthouse
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

North Chatham on Cape Cod 3 bedroom Quaint Guest Home which has been newly restored, taking note of a 3 zone central air conditioning, new yard and a full sun deck with teak dining furniture and a brick patio to grill your favorite steak or fish. Enjoy the starlit sky and on occasion...

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Great Trip

“ Excellent ”
August 20, 2014
We have been coming to Chatham and renting from this owner for almost 25 years. The property is excellent and well appointed and cared for. Love it!!
Meg Minehan, Malta, NY

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Chatham Massachusetts Vacation Rentals - Home
1 / 22

Chatham Home
5 Bedrooms / 5 Bathrooms / Sleeps 11
Home / 5 Bedrooms / Sleeps 11

from

$443

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:11
Type:Home
Per night:$443 - $543
Per week:$3,100 - $3,800
Pets allowed:No
Internet:Yes

Nestled away in a private location with a wooded setting, this large rambling house has all of the comforts of home! This rental property offers sleeping for 11 with two master bedrooms, each with a King Size Bed, cable tv and private bath (one master steps out to small balcony...

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Chatham Massachusetts Vacation Rentals - Home
1 / 25

Chatham Home
4 Bedrooms / 3 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$400

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$400 - $615
Per week:$2,800 - $4,300
Pets allowed:Yes
Internet:Yes

68 Summer Hill Lane CHATHAMCharming Large Post and Beam Cape Style home privately nestled on a quiet lane. 4 bedrooms and 3 bathrooms. Open kitchen/dining/living room floor plan. Spacious Great Room with cathedral ceilings, central A/C, master suite away from main living area. Private...

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Chatham Massachusetts Vacation Rentals - Home
1 / 27

Chatham Home
4 Bedrooms / 2 Bathrooms / Sleeps 9
Home / 4 Bedrooms / Sleeps 9

from

$358

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:9
Type:Home
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:Yes

Schoolhouse Pond just 1/10 mile! Charming custom remodeled Cape Cod home, 1/10 mile to Schoolhouse Pond Beach- - perfect for freshwater beach lovers. First floor offers open kitchen / living area with wall AC unit and one first floor queen bedroom with a ceiling fan. Second floor...

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Chatham Massachusetts Vacation Rentals - Home
1 / 24

Chatham Home
4 Bedrooms / 5 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:5
Sleeps:8
Type:Home
Per night:$2,072
Per week:$14,500
Pets allowed:No
Internet:Yes

464 Shore RdThis waterfront vacation home has a heated pool and magnificent views from every angle, with four bedrooms this sophisticated contemporary home is perfectly appointed and close to the charming town center and glorious beaches. A fabulous master bedroom has a dramatic ...

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Chatham Massachusetts Vacation Rentals - Home
1 / 20

Chatham Home
4 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

(1)“ Excellent ”1 Review

from

$845

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$845 - $1,275
Per month:$25,350 - $38,250
Pets allowed:Yes
Internet:Yes

Pet Friendly! Nothing beats this luxury 4 bedroom, 4. 5 bath Vacation Rental located in the heart of Chatham’ s historic village ! ! Whether you are soaking in the hot tub on the private patio or enjoying an outdoor shower after you’ ve come home from Lighthouse or...

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Chatham Massachusetts Vacation Rentals - Home
1 / 11

Chatham Home
6 Bedrooms / 4 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

from

$358

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:12
Type:Home
Per night:$358 - $422
Per week:$2,500 - $2,950
Pets allowed:No
Internet:Yes

Wonderful vacation home on one acre of land. Very private backyard in Charming Chatham. Boasts all of the amenities, newly rennovated kitchen and bathrooms, air conditioning units in all bedrooms and living areas. Close to town, School House Lake, Beaches, and Cape Cod Bike Trail....

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Chatham Massachusetts Vacation Rentals - Home
1 / 12

Chatham Home
4 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$672

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$672 - $679
Per week:$4,700 - $4,750
Pets allowed:No
Internet:Yes

Lovely renovated home with central air just steps away from Lighthouse Beach. Lovely renovated home just 5 doors down from beautiful Lighthouse Beach- you don t have to worry about parking! This home features many upgrades including central air conditioning and lovely, comfortable...

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Chatham Massachusetts Vacation Rentals - Home
1 / 17

Chatham Home
5 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 5 Bedrooms / Sleeps 8

from

$272

/ night

Email Owner
Bedrooms:5
Bathrooms:2
Sleeps:8
Type:Home
Per night:$272 - $422
Per week:$1,900 - $2,950
Pets allowed:No
Internet:Yes

195 Cedar Street Chatham - ID# 106000Location, location, location! Only a half mile to the beach at Oyster Pond and 3/4 mile to the Village of Chatham. Located on the Chatham Loop, a great walking/jogging/biking route. Wonderful newly renovated home including a fabulous new kitchen...

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Chatham Massachusetts Vacation Rentals - Home
1 / 9

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$300

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$300
Per week:$2,100
Pets allowed:Yes
Internet:Yes

Charming cape- style pet friendly home close to all that the village has to offer. PET FRIENDLY Charming cape- style home close to all that the village has to offer. Walk to town, Oyster Pond, Chatham Anglers games, golf, and tennis courts. This home is pet friendly. $2100/week...

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Chatham Massachusetts Vacation Rentals - Apartment
1 / 7

Chatham Apartment
1 Bedroom / 1 Bathroom / Sleeps 2
Apartment / 1 Bedroom / Sleeps 2

from

$150

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$150 - $193
Per week:$1,050 - $1,350
Pets allowed:No
Internet:Yes

73 Main Street, Unit #8Charming second- story condominium apartment located right across the street from Lighthouse Beach. Views of the beach from deck off the living room. Walk across the street to Lighthouse Beach and also within walking distance to the Village. NO pets accepted....

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Chatham Massachusetts Vacation Rentals - Home
1 / 11

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(2)“ Excellent ”2 Reviews

from

$143

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$143 - $186
Per week:$1,000 - $1,300
Pets allowed:No
Internet:Yes

Walk to Taylors Pond with Association Beach, Close to Cockle Cove, WIFI - GREAT LOCATION! This cheerful, open floor plan ranch is a 5 minute walk to the deeded beach on Taylors Pond: a salt water pond connected to Nantucket Sound by the Mill Creek salt marsh; excellent for kayaking/canoeing....

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Chatham Massachusetts Vacation Rentals - Home
1 / 14

Chatham Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$343

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$343 - $472
Per week:$2,400 - $3,300
Pets allowed:No
Internet:Yes

WALK TO TOWN LOCATION! ! Spectacular rental property located just a short walk to restaurants, shops, Chatham Bars Inn, Seaside Links 9 Hole Golf Course, Chatham Angler's Ballfield, town playground and Oyster Pond beach area. This immaculate rental has so much to offer.... four...

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Chatham Massachusetts Vacation Rentals - Home
1 / 18

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

(2)“ Excellent ”2 Reviews

from

$197

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$197 - $383
Per week:$1,375 - $2,675
Pets allowed:No
Internet:Yes

Waterfront on Lovers Lake, 1 AC & WIFI - This lovely 3 bedroom, 2 bath ranch features a private, sandy beach right on Lovers Lake (one of Cape Cod's beautiful, glacier- formed kettle ponds); ideal for swimming or bring your kayak and enjoy the serenity. This property is located...

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Chatham Massachusetts Vacation Rentals - Home
1 / 14

Chatham Home
3 Bedrooms / 4 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$158

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:6
Type:Home
Per night:$158 - $315
Per week:$1,100 - $2,200
Pets allowed:No
Internet:Yes

Beautifully updated ranch in ChathamGorgeous fully renovated home in a quiet neighborhood. Open floor plan with a lovely kitchen featuring granite countertops. Central air conditioning, hardwood floors and wireless internet are just a few of the amenties for a comfortable vacation....

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Chatham Massachusetts Vacation Rentals - Home
1 / 15

Chatham Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$500

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$500 - $715
Per week:$3,500 - $5,000
Pets allowed:No
Internet:Yes

105 Wood Carver Knoll, Chatham - ID# 106342. Spectacular waterfront home in Chatham overlooking Oyster Pond! Central Air, gourmet kitchen with espresso machine, keurig and more. Enjoy the deck with incredible views of Oyster Pond, the church steeples of Main St, tidal marshes...

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Chatham Massachusetts Vacation Rentals - Apartment
1 / 13

Chatham Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$150

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$150 - $250
Per week:$1,050 - $1,750
Pets allowed:No
Internet:Yes

11 CHATHAM BARS AVENUEVery attractive and spacious second story condominium. Located in the true heart of the village, and just a short walk to Claflin Landing beach. $1750 per week in season + $120 cleaning fee and $55 Vacation Rental Damage Coverage Fee (VRD), $60 Handling Fee,...

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Chatham Massachusetts Vacation Rentals - Home
1 / 15

Chatham Home
4 Bedrooms / 2 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Sophisticatedly furnished and well maintained 4BR/2BA Cape style home accessible to Pleasant Street Beach, local restaurants, and shopping on Main Street in Chatham. Spacious living throughout, a fully equipped new granite kitchen, gas range, and stainless appliances. Two large...

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Chatham Massachusetts Vacation Rentals - Home
1 / 17

Chatham Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

The charming, sprawling ranch has 4 bedrooms and 3 baths. There is a spacious living room, dining room, large deck, all with spectacular views overlooking Pleasant Bay. This property has access to its own private beach as well as a float tie- up for a boat up to 24'. Amenities...

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Chatham Massachusetts Vacation Rentals - Home
1 / 14

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

You'll have fantastic views of Nantucket Sound from this 3 bedroom 2 bath traditional Chatham vacation rental only 1/10th of a mile from Ridgevale beach. There is a large deck to relax on and enjoy the sun setting over Nantucket Sound. The property offers a gas grill, a new enclosed...

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Chatham Massachusetts Vacation Rentals - Home
1 / 1

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

52 PLEASANT STREETEasy access to Pleasant Street Beach. The property has 3 bedrooms, two with 2 single beds and one with a queen size bed all on one level. Amenities include an enclosed porch, outside shower and WIFI. This property rents for $1, 700 per week in season. Please view...

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Chatham Massachusetts Vacation Rentals - Home
1 / 13

Chatham Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Lovely updated home near Jackknife Cove Beach on Pleasant BayLovely updated home in close proximity to Ryder s Cove and Jackknife Cove Beach on Pleasant Bay. This home is in excellent condition and features 3 bedrooms, a nice back yard and is fully air conditioned. The home rents...

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Chatham Massachusetts Vacation Rentals - Home
1 / 14

Chatham Home
4 Bedrooms / 2 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

(2)“ Excellent ”2 Reviews

from

$358

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Home
Per night:$358 - $500
Per week:$2,500 - $3,500
Pets allowed:Yes
Internet:Yes

WATERFRONT PRIVATE RETREAT ON FRESHWATER GOOSE POND! ! ! Nestled away in a serene setting to enjoy lots of privacy and a perfect swimming spot. Casual setting... house has a rustic feel. House is now listed as a pet friendly rental! Large deck faces the water, expansive livingroom...

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Chatham Massachusetts Vacation Rentals - Home
1 / 22

Chatham Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$225

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$225 - $378
Per month:$6,750 - $11,340
Pets allowed:No
Internet:No

Located in Chatham, this 4 bedroom 2 bath Cape Cod vacation rental home has window A/C units in the upstairs bedrooms as well as the 1st floor bedroom and living area to keep you cool and offers WiFi to keep you connected. . 3 miles to Ridgevale Beach. Through the side door off of...

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Chatham Massachusetts Vacation Rentals - Home
1 / 21

Chatham Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$543

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$543 - $643
Per week:$3,800 - $4,500
Pets allowed:No
Internet:Yes

169 Lime Hill Road CHATHAMThis magnificent and well- appointed home is the epitome of luxury living with added Cape Cod style. Conveniently located less than 3/4 of a mile from Chatham Village, you also have deeded rights to a path to Oyster Pond.. Every amenity is provided, from...

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Chatham Massachusetts Vacation Rentals - Home
1 / 38

Chatham Home
5 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 5 Bedrooms / Sleeps 8

from

$800

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:8
Type:Home
Per night:$800
Per week:$5,600
Pets allowed:Yes
Internet:No

New Listing for 2015! Peak Summer Rates - - $5600Located in a premier Chatham Village location, this classic antique home has everything to experience an idyllic Chatham vacation. Park your car in the driveway and leave it for the week! Walk to everything: downtown Chatham is ...

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Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$250

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$250 - $385
Per month:$7,500 - $11,550
Pets allowed:Yes
Internet:No

Pet Friendly. Relax in this 3 bedroom, 2 bath Cape Cod Vacation home in Chatham that is conventient to downtown Chatham and beaches. Privacy abounds just Off Main St. and the home even overlooks a working Cranberry Bog! Window A/C units in Bedrooms and Wifi too. An open spacious...

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Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
4 Bedrooms / 4 Bathrooms / Sleeps 13
Home / 4 Bedrooms / Sleeps 13

Bedrooms:4
Bathrooms:4
Sleeps:13
Type:Home
Per night:$1,286
Per week:$9,000
Pets allowed:Yes
Internet:No

$7, 900 PRIME SUMMER WEEKLY RATEThis classic home is perched in the dunes of Chatham, just to the south of Chatham Light. This large home is ideal for larger groups looking for a perfect Chatham experience. The home has 4 bedrooms, 4 full baths, a modern kitchen, central AC, ...

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Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
6 Bedrooms / 7 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

Bedrooms:6
Bathrooms:7
Sleeps:12
Type:Home
Per night:$2,500
Per week:$17,500
Pets allowed:No
Internet:No

$18, 500 PRIME SUMMER WEEKLY RATEThis exquisite North Chatham estate is located in one of Chatham' s most premier neighborhoods on Old Harbor Road. Set far back from the road on over 2 acres, this property provides stunning elevated views of Chatham Harbor, North Island and...

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Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
3 Bedrooms / 4 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

Bedrooms:3
Bathrooms:4
Sleeps:6
Type:Home
Per night:$1,065
Per week:$7,450
Pets allowed:No
Internet:No

$6, 500 PRIME SUMMER WEEKLY RATEThis stunning home was featured in a local periodical for outstanding renovation. The home features multiple living areas, a gourmet kitchen, 2 master suites with private baths (plus a third spacious bedroom with a queen) and several outdoor living...

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Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
6 Bedrooms / 7 Bathrooms / Sleeps 16
Home / 6 Bedrooms / Sleeps 16

Bedrooms:6
Bathrooms:7
Sleeps:16
Type:Home
Per night:$1,475
Per month:$44,250
Pets allowed:Yes
Internet:Yes

Pet Friendly! Relax and enjoy this Chatham, Cape Cod Vacation Rental Home 6 bedroom 6. 5 bath luxury home that is pet friendly with private pool, central a/c, linens, wifi and more. In historic village of Chatham and . 2 to Lighthouse beach. This restored and completely updated...

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Chatham Massachusetts Vacation Rentals - Home
1 / 24

Chatham Home
6 Bedrooms / 2 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

from

$600

/ night

Email Owner
Bedrooms:6
Bathrooms:2
Sleeps:12
Type:Home
Per night:$600 - $914
Per month:$18,000 - $27,420
Pets allowed:Yes
Internet:No

Pet Friendly! ! High atop Sears Point in Chatham sits a Classic, Quintessential, New England Bluff house overlooking the sparkling, blue sea. This spot is a boater’ s paradise! From kayaking to boating enthusiasts :There is a mooring available for your use (reserve ahead...

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Chatham Home
4 Bedrooms / 5 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

(1)“ Excellent ”1 Review

Bedrooms:4
Bathrooms:5
Sleeps:10
Type:Home
Per night:$1,125 - $1,785
Per month:$33,750 - $53,550
Pets allowed:No
Internet:Yes

Paradise found on the shores of Eastward Point in Chatham! Luxury at its finest will surround you at every turn in this renovated, contemporary Cape Cod Vacation home offering central air and wireless internet. With over 4000 square feet, the open floor plan makes for easy living....

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Chatham Massachusetts Vacation Rentals - Home
1 / 16

Chatham Home
4 Bedrooms / 3 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$285

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$285 - $300
Per month:$8,550 - $9,000
Pets allowed:Yes
Internet:Yes

Pet Friendly! Classic Cape Cod Vacation Home Rental in Chatham near Schoolhouse Pond for freshwater swimming. It is located in a residential area and is convenient to the Cape Cod Bike trail, and the Chatham Airport and restaurant (Hanger B eatery). It has 3 a/c units and wifi too....

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Chatham Massachusetts Vacation Rentals - Home
1 / 20

Chatham Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$457

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$457
Per month:$13,710
Pets allowed:No
Internet:No

Location - Location - Location! Run, walk or skip the loop in Chatham from this Family Cape Cod Vacation Rental home. It’ s just a 5 minute stroll to the town landing to put your kayak or canoe in and spend the day on the water. Just 1. 1 Mile to Oyster Pond and an easy...

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Chatham Massachusetts Vacation Rentals - Home
1 / 18

Chatham Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$285

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$285 - $492
Per month:$8,550 - $14,760
Pets allowed:No
Internet:No

This Cape Cod Vacation Rental Home is located on a dead end street , in a central Chatham location so you can walk to Oyster Pond , also into the downtown Village of Chatham and enjoy all that this seaside village has to offer. It has plenty of space for all to enjoy, Central A/C...

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Chatham Massachusetts Vacation Rentals - Home
1 / 23

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$375

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$375 - $600
Per month:$11,250 - $18,000
Pets allowed:No
Internet:No

Location - Location- Location! ! This Cape Cod Vacation Rental Home is located in the Old Village of Chatham. It has been lovingly restored to keep the Cape Cod Traditional Charm with all modern amenities. It has been updated with an open Chef' s gourmet kitchen and new bathrooms...

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Chatham Massachusetts Vacation Rentals - Home
1 / 15

Chatham Home
2 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

from

$225

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$225
Per month:$6,750
Pets allowed:Yes
Internet:No

Pet Friendly. Come have some fun in the sun at this Cape Cod Vacation cottage in Chatham! You will enjoy deeded access to the "Little Beach flats" and stroll just a half mile up to Lighthouse Beach- it' s also an easy bike ride into the village! The cottage offers a main floor...

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About Chatham

Chatham, MA Travel Tips

Situated on the southeastern tip of Cape Cod is the town of Chatham, MA. This charming town is a pleasant place for families to unwind and spend valuable and fun time together. For the most relaxing experience possible, people will want to skip hotels in favor of Chatham rentals. For the best selection of Chatham vacation rentals online, you're in the right place. Vacation Home Rentals has well-maintained properties available for rent by owner. By booking with us, you can save money and enjoy the comforts of home. When planning a trip to Chatham, there are a few tips that can make the stay more comfortable for all.
During the winter, Chatham is quieter than in the busy summer months. For families that prefer to avoid crowds, this is a good time to visit. Keep an eye on the average temperatures for the month that you'll be visiting Chatham. The warmest months of the year are July and August, with top temperatures averaging 75 degrees Fahrenheit. The coldest month of the year is January, with average lows at 24 degrees Fahrenheit and highs at 38 degrees Fahrenheit. Checking out the weather will help make packing for the family easier. When traveling in peak season, be sure to book Chatham vacation rentals in advance to save time and money.

Attractions

Rest and relaxation are two of the most important reasons why tourists stay in vacation rentals. Chatham, MA, has so many attractions that at the end of a fun-filled day, families will appreciate a good night's sleep. A popular destination for families is the Atwood House Museum. The museum is a great way to learn about the history of Cape Cod and to view the area's art while staying in Chatham, MA, rentals. Another interesting museum to visit is the Chatham Railroad Museum, which is located in an 1887 railroad depot that has been restored. The Chatham Lighthouse is another popular destination when visiting the city. To visit the lighthouse, tourists may arrange for a tour on dates that have been set aside by the Coast Guard Auxiliary. For many tourists staying in Chatham rentals, the beaches are one of the main attractions. Public beaches include Ridgevale Beach, Harding Beach, Cockle Cove Beach, and more. Parks are another way that families can enjoy their vacation. Parks such as Chase Park offer great outdoor fun and have picnic areas and charcoal grills. Also located in Chatham is the Monomoy National Wildlife Refuge, Samuel Hawes Park, Sears Park, and ...

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