Chatham Vacation Rentals, Homes, & More

1-50 of 214 Chatham Rentals

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Cape Cod Emery Pond
1 / 37
Bedrooms:4
Bathrooms:2.5
Sleeps:10
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

July 12th week still available! Cleaning Fee: 175. 00 ON THE WATER ... Beautiful water views! Back decks open up to mesmerizing views of Emery Pond featuring a new hammock and patio furniture chosen for comfort and relaxation! Direct access to pond from backyard....

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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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PLEASANT STREET - NORTHERN VIEW
1 / 14

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”10 Reviews

from

$225

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$225 - $300
Per month:$6,750 - $9,000
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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Exterior View of Cranberry Way
1 / 11

Chatham Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”11 Reviews

from

$150

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$150 - $190
Per month:$4,500 - $5,700
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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Great weekend

“ Excellent ”
September 3, 2014
Beds were comfortable. Kitchen had all the pots, pans, dishes and utensils you could need. The kitchen had no supplies like tea, coffee or sugar (most places we have stayed at have those basics). Very quiet dead end road. We would recommend This home to friends.
Angela Derrane, Utica, NY

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Chatham Massachusetts Vacation Rentals - Home
1 / 8

Chatham Home
9 Bedrooms / 4 Bathrooms / Sleeps 20

“ 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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1 / 37

Chatham Home
4 Bedrooms / 3 Bathrooms / 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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1 / 10

Chatham Cottage
2 Bedrooms / 1 Bathroom / Sleeps 6

“ Excellent ”4 Reviews

from

$93

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Cottage
Per night:$93 - $158
Per week:$650 - $1,100
Pets allowed:No
Internet:Yes

$1050/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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Bedroom with sky window
1 / 4

Chatham Apartment
2 Bedrooms / 2 Bathrooms / 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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1 / 6

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ 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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Great Walk-To-Town location
1 / 16

Chatham Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 8

“ Excellent ”3 Reviews

from

$358

/ night

Email Owner
Bedrooms:4
Bathrooms:2.5
Sleeps:8
Type:Home
Per night:$358 - $643
Per week:$2,500 - $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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Fore Ceas Guest Home
1 / 22

Chatham Guesthouse
3 Bedrooms / 3.5 Bathrooms / Sleeps 6

“ Excellent ”8 Reviews

from

$288

/ night

Email Owner
Bedrooms:3
Bathrooms:3.5
Sleeps:6
Type:Guesthouse
Per night:$288 - $602
Per month:$8,640 - $18,060
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 / 25

Chatham Home
4 Bedrooms / 3 Bathrooms / 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

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

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 / 10

Chatham Home
6 Bedrooms / 2 Bathrooms / Sleeps 11

from

$393

/ night

Email Owner
Bedrooms:6
Bathrooms:2
Sleeps:11
Type:Home
Per night:$393 - $608
Per week:$2,750 - $4,250
Pets allowed:Yes
Internet:Yes

209 Champlain Rd Chatham MADOG FRIENDLY Great, rambling home with an old- Cape Cod feel located on the "loop" just around the bend from Stage Harbor. Wonderful area for walking and biking and a tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge,...

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Chatham Massachusetts Vacation Rentals - Home
1 / 36

Chatham Home
5 Bedrooms / 3 Bathrooms / Sleeps 10

from

$750

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:10
Type:Home
Per night:$750
Per week:$5,250
Pets allowed:No
Internet:Yes

369 Shore RoadLovely five bedroom home close to town and the beach! It has everything you need: a huge yard for games, central air, updated kitchen and an awesome location! The beach is just a walk across the street from this beautifully landscaped Shore Road home. This home is...

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Chatham Massachusetts Vacation Rentals - Home
1 / 11

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

from

$286

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$286 - $500
Per week:$2,000 - $3,500
Pets allowed:No
Internet:Yes

185 Indian Hill Road - Property ID: 99369Gorgeous home very close to the Cape Cod Bike Trail and School House Pond! This home offers access to pools, tennis courts, fitness center, and activities at Ocean Edge Resort & Golf Club in Brewster, MA at an additional charge to the ...

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Chatham Massachusetts Vacation Rentals - Home
1 / 21

Chatham Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$458

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$458 - $529
Per week:$3,200 - $3,700
Pets allowed:No
Internet:Yes

Classic old- style Cape Cod home overlooking Chatham Harbor with private stairs leading down to Lighthouse Beach. SUNDAY arrival and departure this Classic old- style Cape Cod living in a simply spectacular location. This 4 bedroom home inside the Old Village Historic District overlooks...

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Chatham Massachusetts Vacation Rentals - Home
1 / 12

Chatham Home
4 Bedrooms / 4 Bathrooms / 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

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
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$172

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$172 - $358
Per week:$1,200 - $2,500
Pets allowed:No
Internet:Yes

Lovely 2 bedroom home located in a prime location between Lighthouse Beach and Chatham Village. Charming, well maintained home in a fabulous location in Chatham s Old Village. The home is less than 1/2 mile to both Lighthouse Beach and the quaint village of Chatham s shops and restaurants....

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Chatham Massachusetts Vacation Rentals - Home
1 / 9

Chatham Home
3 Bedrooms / 2 Bathrooms / 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 - Home
1 / 1

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$172

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$172
Per week:$1,200
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 - Cottage
1 / 13

Chatham Cottage
2 Bedrooms / 1 Bathroom / Sleeps 4

from

$258

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Cottage
Per night:$258
Per week:$1,800
Pets allowed:No
Internet:Yes

96 Water Street CHATHAMCharming light and bright 2 bedroom cottage in the Old Village, within walking distance to both town and Lighthouse Beach. The cottage shares a yard with the Main house. This property rents for $1, 800 per week in season. call 1 508 945 7777 EXT 1144 or email...

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Chatham Massachusetts Vacation Rentals - Apartment
1 / 7

Chatham Apartment
1 Bedroom / 1 Bathroom / 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
4 Bedrooms / 2 Bathrooms / Sleeps 8

from

$229

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$229
Per week:$1,600
Pets allowed:Yes
Internet:Yes

Pet friendly home with central airComfortable 4 bedroom cape on a quiet street in Riverbay Estates. Convenient to Schoolhouse Pond and Jackknife Cove beach on Pleasant Bay. This home has central air conditioning, an enclosed outside shower, and is PET FRIENDLY. This property rents...

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Chatham Massachusetts Vacation Rentals - Home
1 / 16

Chatham Home
4 Bedrooms / 2 Bathrooms / Sleeps 8

from

$172

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$172 - $558
Per week:$1,200 - $3,900
Pets allowed:No
Internet:Yes

NEWER UPDATED HOME WITH LOVELY VIEWS OF STETSON COVE! Central air conditioning, wireless internet, family room with queen futon and cable televison! Alcove off the living room has a second television. First floor laundry room. House has lots of living space. Spacious, immaculate...

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Chatham Massachusetts Vacation Rentals - Home
1 / 16

Chatham Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

from

$658

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$658
Per week:$4,600
Pets allowed:No
Internet:Yes

155 LIME HILL ROAD CHATHAMLarge and lovely 4 bedroom home built to a very high standard. Just a short distance to Chatham Village and all it has to offer. Beautiful yard and grounds, this home is a joyful place in the summertime. Offering 4 comfortable bedrooms, a generous kitchen...

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Chatham Massachusetts Vacation Rentals - Home
1 / 9

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$400

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$400
Per month:$12,000
Pets allowed:No
Internet:No

This Cape Cod Vacation Rental home is just . 2 miles from Pleasant Street Beach in Chatham. Warm water, sunsets and miles of beach on Nantucket Sound awaits you just around the corner. This family friendly updated Cape Cod ranch has a large deck for outdoor entertaining surrounded...

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Chatham Massachusetts Vacation Rentals - Home
1 / 16

Chatham Home
4 Bedrooms / 3 Bathrooms / Sleeps 10

from

$179

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$179 - $243
Per week:$1,250 - $1,700
Pets allowed:No
Internet:Yes

190 Countryside Drive - ID# 104736. Lovely 4 bedroom home in ChathamCharming 4 bedroom home in a peaceful area with a lovely fenced in yard. Just a short drive to Jackknife Cove beach on Pleasant Bay and a short distance to Monomoy River for kayaking and canoeing. Chatham Village...

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Chatham Massachusetts Vacation Rentals - Home
1 / 21

Chatham Home
4 Bedrooms / 3 Bathrooms / 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 / 12

Chatham Home
5 Bedrooms / 3 Bathrooms / Sleeps 9

from

$272

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:9
Type:Home
Per night:$272 - $358
Per week:$1,900 - $2,500
Pets allowed:No
Internet:Yes

60 Hallet Lane - ID# 104906. In the heart of the Old VillageAntique home in the heart of Old Chatham Village. Convenient to Lighthouse Beach, Village shops and restaurants. Five Bedroom, 3 Bath, 4/10 mile to Lighthouse Beach. $2500 per week in season with a $210 Cleaning Fee. ...

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Chatham Massachusetts Vacation Rentals - Home
1 / 11

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ 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 / 18

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ 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 / 15

Chatham Home
3 Bedrooms / 3 Bathrooms / 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 - Home
1 / 16

Chatham Home
5 Bedrooms / 5 Bathrooms / Sleeps 16

Bedrooms:5
Bathrooms:5
Sleeps:16
Type:Home
Per night:$1,072 - $1,372
Per week:$7,500 - $9,600
Pets allowed:No
Internet:Yes

Gorgeous 5 bedroom, 4. 5 bath home in Chatham! Property ID: 107477 / Key #: 107477Beautiful modern 5 bedroom waterfront home on over an acre overlooking Chatham s Oyster Pond. Enjoy panoramic views of the water and marsh in one of Chatham s finer locations. Situated on the Pond,...

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Chatham Massachusetts Vacation Rentals - Home
1 / 14

Chatham Home
3 Bedrooms / 4 Bathrooms / 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 / 7

Chatham Home
4 Bedrooms / 2 Bathrooms / Sleeps 8

from

$300

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$300 - $543
Per week:$2,100 - $3,800
Pets allowed:No
Internet:Yes

LOCATED IN THE HEART OF THE OLD VILLAGE! this charming renovated antique home is just a short walk to Lighthouse Beach and to Town! The perfect location in Chatham! Central Air Conditioning, wireless interent access, comfortable interior with new living room furniture this year,...

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Chatham Massachusetts Vacation Rentals - Home
1 / 20

Chatham Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$675

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$675 - $1,000
Per month:$20,250 - $30,000
Pets allowed:No
Internet:No

Contemporary Chatham vacation home with heated salt water gunite pool (It' s like a bath of silk, doesn' t burn the eyes, no issue with anyone' s hair turning green, feels like you are in a bath of evian! ) Just a short walk to Harding’ s Beach (. 3) - Chatham'...

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Chatham Massachusetts Vacation Rentals - Apartment
1 / 9

Chatham Apartment
1 Bedroom / 1 Bathroom / Sleeps 4

from

$136

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$136 - $161
Per week:$950 - $1,125
Pets allowed:No
Internet:Yes

GREAT LOCATION DIRECTLY ACROSS FROM LIGHTHOUSE BEACH! ! Sought after Old Village location, immaculate 1 bedroom condo with one bedroom/one bath, open small kitchen/living room area, queen size bed in the bedroom and pullout queen sofa in the living room. Enjoy the waterviews of...

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Chatham Massachusetts Vacation Rentals - Home
1 / 8

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$179

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$179 - $258
Per week:$1,250 - $1,800
Pets allowed:Yes
Internet:Yes

241 Training Field RoadCharming and updated 3 bedroom air conditioned ranch style home just 1 mile from beautiful Pleasant Bay at Jacknife Point Beach. $1800 per week in season plus $160 Cleaning Fee, $60 Handling Fee, made outto Bruce Court & $55 Vacation Rental Damage Fee. To ...

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Chatham Massachusetts Vacation Rentals - Apartment
1 / 14

Chatham Apartment
2 Bedrooms / 2 Bathrooms / 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 / 18

Chatham Home
6 Bedrooms / 4 Bathrooms / Sleeps 12

from

$786

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:12
Type:Home
Per night:$786
Per week:$5,500
Pets allowed:No
Internet:Yes

455 Shore Road, Chatham - Property ID: 105467 Wonderful Captains House located on the highly desirable Shore Road in Chatham with water views of Chatham Harbor and walking distance to Claflin Landing Beach and Chatham Village! Wonderful Captains House located on the highly desirable...

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Chatham Massachusetts Vacation Rentals - Home
1 / 23

Chatham Home
3 Bedrooms / 3 Bathrooms / Sleeps 10

“ Excellent ”1 Review

from

$325

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:10
Type:Home
Per night:$325 - $500
Per month:$9,750 - $15,000
Pets allowed:No
Internet:No

Enjoy easy resort style living in this newer Cape Cod Vacation Rental home in Chatham. This home is in its own residential sub division and is close to beaches, restaurants, downtown and includes a community pool & tennis court! Central A/C, garage, finished lower level, main...

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Chatham Massachusetts Vacation Rentals - Home
1 / 13

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$186

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$186 - $558
Per week:$1,300 - $3,900
Pets allowed:No
Internet:Yes

JUST A SHORT WALK TO LIGHTHOUSE BEACH and ANDREW HARDINGS LANE! ! ! Old Village Location. This summer rental is immaculate and absolutely adorable. Just 2/10's of a mile to a classic Cape Cod beach and also a short distance to town. Great front porch with rockers and spectacular ...

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Chatham Massachusetts Vacation Rentals - Home
1 / 17

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$278

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$278
Per month:$8,340
Pets allowed:No
Internet:No

Updated Cape Cod Vacation Rental home in Chatham that is . 6 to Pleasant Street Beach and also a very short drive to Red River Beach. Easy access to the bike trail. Refreshed with new paint, comfy furniture, kitchen and baths. Wifi is available for your convenience and each bedroom...

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

338 Seapine Road CHATHAM, ID# 104736Waterfront 3 bedroom home overlooking Bassing Harbor and Fox Hill with the outer barrier beach beyond. Located on a cul de sac in a highly desirable neighborhood, the home is a classic cape in style. Water access for kayaking in Pleasant Bay and...

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

70 Captain Kendrick Drive, ChathamLovely home on a quiet residential street equipped with central a/c. Short drive to beaches, town and shopping. $1475/week in season. $150 Cleaning Fee. Please call 508- 240- 2222 or email vacationinfo@raveis. com to reserve this propertyAdditional...

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Chatham Massachusetts Vacation Rentals - Home
1 / 15

Chatham Home
4 Bedrooms / 2 Bathrooms / 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 - Apartment
1 / 8
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

393 STONY HILL ROAD CHATHAMCharming and completely renovated cottage, 7/10 of a mile to Scatteree Beach and the Cow Yard Landing and under 2 miles to Main St., Chatham for shopping, dining, and ice cream! This adorable one bedroom, air conditioned cottage has vaulted ceilings,...

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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 Volunteer Park.
Events
Hotels are often overcrowded and noisy when the city is hosting a special event. The calm atmosphere and convenience of staying in Chatham, MA, vacation rentals is a benefit for many tourists. Families on vacation will appreciate this convenience and can better enjoy the event's festivities. Festivals, fairs and other events take place throughout the year. In June, for instance, there is the annual Chatham Harbor Run and the Classic Car Invitational. For the children in the family, there are games for kids, while adults can enjoy a beer with their bratwurst and other German fare. Thanksgiving is a great time to travel to and stay in vacation rentals in Chatham, MA. Before indulging in a Thanksgiving Day meal, families can run or walk together in the annual Turkey Trot. Also during the holiday season, don't miss the annual Chatham Christmas Stroll.
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