Chatham Vacation Rentals, Homes, & More

1-50 of 358 Chatham Rentals

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Front View of Cranberry Way, South Chatham
1 / 11

Chatham Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”11 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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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 / 14
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$486
Per week:$3,400
Pets allowed:No
Internet:Yes

PRICE JUST REDUCED! ! ! Four bedroom, 2 full bathrooms in private residental area in North Chatham. Many updates have been done this year including granite in kitchen, wood floors throughout, enlarged deck in backyard. Large great room, spacious kitchen, enclosed porch w/skylights...

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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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Chatham Massachusetts Vacation Rentals - Guesthouse
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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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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PLEASANT STREET - NORTHERN VIEW
1 / 14

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 8

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

This beautiful newer home is located in Hardings Beach Hills 5/10ths of a mile from Harding's Beach. The property borders Buck's Creek and the house is very tastefully decorated and has nearly every amenity including washer/dryer, dishwasher, central air, cable TV (includes NESN)...

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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 - $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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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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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 / 15

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

Chatham Home
2 Bedrooms / 1 Bathroom / Sleeps 4

from

$250

/ night

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

Great views of the Atlantic, Beach is across the street. Two bedrooms one with a double and the other with bunks. Next to Chatham Lighthouse. Near restaurants and downtown Chatham. This is a great location, _Additional amenities include: single beds(1), double beds(1), general...

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Chatham Massachusetts Vacation Rentals - Home
1 / 7
Bedrooms:5
Bathrooms:5
Sleeps:16
Type:Home
Per night:$1,300
Per week:$9,100
Pets allowed:No
Internet:Yes

Saltwater waterfront location on beautiful Oyster Pond. Capture spectacular sunrises with unobstructed panoramic water and town views from the large first and second floor windows, brick patio, grassy yard and second floor balcony of this modern 4000 plus sq. ft. Cape- style home....

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Chatham Massachusetts Vacation Rentals - Home
1 / 7

Chatham Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$500

/ night

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

This home is a lovely contemporary cape on over an acre lot. Deeded rights to a private association beach. There are two bedrooms on the main floor and one on the lower level. Extra space above garage. There is also a family room on the lower level. Located at 129 Attucks Trail, ...

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Chatham Massachusetts Vacation Rentals - Home
1 / 22

Chatham Home
3 Bedrooms / 4 Bathrooms / Sleeps 10

from

$500

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:10
Type:Home
Per night:$500 - $715
Per week:$3,500 - $5,000
Pets allowed:No
Internet:Yes

105 Queen Anne RoadWater views from this beautifully maintained home located just around the corner to downtown Chatham and 1/10 of a mile to the beach on Oyster Pond! All the amenities including central AC, WIFI, outside shower & gas grill. 3 bedrooms each with full baths and ...

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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 / 10

Chatham Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$483

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$483 - $643
Per week:$3,375 - $4,500
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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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 / 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 / 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 / 19

Chatham Home
3 Bedrooms / 4 Bathrooms / Sleeps 8

from

$429

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:8
Type:Home
Per night:$429 - $858
Per week:$3,000 - $6,000
Pets allowed:No
Internet:No

Lovely bright home with waterviews and central A/C in North ChathamStunning, beautifully furnished and decorated home with central A/C and views of Pleasant Bay out to the Atlantic is located in a lovely area of North Chatham. This reverse floor plan home with the living areas on...

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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 / 11

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$229

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$229
Per week:$1,600
Pets allowed:No
Internet:Yes

454 Training Field Road CHATHAMLovely updated 3 bedroom home in close proximity to Pleasant Bay and Jackknife Cove beach. Just a few minutes drive to the quaint downtown village of Chatham. This home rents for $1700 per week in season. Additional amenities include: sofabed, coffee...

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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 / 13

Chatham Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$486

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$486
Per week:$3,400
Pets allowed:No
Internet:Yes

Lovely home sleeps 6 people comfortably. 3 bedroom, 3 baths. Outdoor shower, 2 car garage and large back yard deck are just some of the great features of this home. Please call for availability. Additional amenities include: smoke free, queen beds(1), general amenities, king ...

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Chatham Massachusetts Vacation Rentals - Home
1 / 7

Chatham Home
4 Bedrooms / 2 Bathrooms / Sleeps 8

from

$386

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$386
Per week:$2,700
Pets allowed:No
Internet:Yes

This is a lovely four bedroom two bath home with views of Oyster River and Nantucket Sound from the front of the property and deck. The first floor has a bright living room, dining area, kitchen, full bath with washer and dryer and two bedrooms, one with twins and the second with...

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Chatham Massachusetts Vacation Rentals - Home
1 / 11

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:Yes

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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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 / 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 / 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:Yes

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 / 20

Chatham Home
4 Bedrooms / 4 Bathrooms / Sleeps 10

“ 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 Andrew Harding's...

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Chatham Massachusetts Vacation Rentals - Home
1 / 22

Chatham Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$542

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$542
Per month:$16,260
Pets allowed:No
Internet:Yes

This Cape Cod Vacation Rental is located in Chatham's Old Village and is right on the Mill Pond. The Old Village is popular for its historic nature and architectural beauty. Witness beautiful sunset views from the patio. It is a short walk to Chatham Village (. 2) and Lighthouse Beach...

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Chatham Massachusetts Vacation Rentals - Home
1 / 14

Chatham Home
2 Bedrooms / 1 Bathroom / Sleeps 6

from

$192

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Home
Per night:$192
Per month:$5,760
Pets allowed:No
Internet:Yes

Quintessential Cape Cod Vacation Rental Cottage in Chatham on the way to Cockle Cove Beach. Enjoy this Cape Cod beach cottage with casual coastal decor. A/C units in Living area and bedrooms and Wifi too. This home offers 2 bedrooms and a full bath with Tub/Shower. As you walk in ...

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Chatham Massachusetts Vacation Rentals - Home
1 / 24

Chatham Home
6 Bedrooms / 2 Bathrooms / 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:Yes

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 of time)...

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Chatham Massachusetts Vacation Rentals - Home
1 / 18

Chatham Home
4 Bedrooms / 2 Bathrooms / Sleeps 10

from

$485

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Home
Per night:$485
Per month:$14,550
Pets allowed:Yes
Internet:Yes

Pet Friendly! Spend Lazy summer days at this Cape Cod Vacation rental in Chatham. With the shade from the pines, the spray of sea salt from the Nantucket Sound and the warm summer sun, you are sure to have a relaxing escape to the Cape. From kayaking (2 included! ) to boating ...

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Chatham Massachusetts Vacation Rentals - Home
1 / 20

Chatham Home
4 Bedrooms / 3 Bathrooms / Sleeps 9

from

$525

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:9
Type:Home
Per night:$525 - $625
Per month:$15,750 - $18,750
Pets allowed:No
Internet:Yes

Paradise Found at this special retreat in this Cape Cod Vacation home Rental in Chatham called the Heron's Nest! This spacious , Four Bedroom, 3 bath luxury Chatham Rental will surely delight you in every way. Just a half mile to the warm waters and gentle waves of Ridgevale beach...

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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:Yes

Popular Contemporary Cape Cod Vacation Rental home in Chatham with heated salt water gunite pool that is just a short walk to Hardings Beach (. 3). Don't miss this "fan favorite" Cape Cod Vacation Rental home in Chatham with heated pool that is very close to Hardings Beach (. 3 Chatham's...

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Chatham Massachusetts Vacation Rentals - Home
1 / 15

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$250

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$250 - $357
Per month:$7,500 - $10,710
Pets allowed:Yes
Internet:Yes

Pet Friendly! Enjoy this Cape Cod Vacation Rental cottage in Chatham offering 3 bedrooms and 2 baths at the end of a small lane, across from the ocean. The first floor contains a large living room with flat screen TV and Wireless Internet, combined kitchen/dining room, washer ...

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Chatham Massachusetts Vacation Rentals - Home
1 / 18

Chatham Home
3 Bedrooms / 4 Bathrooms / Sleeps 8

“ Excellent ”1 Review

from

$400

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:8
Type:Home
Per night:$400 - $714
Per month:$12,000 - $21,420
Pets allowed:Yes
Internet:Yes

Charming, fully renovated Sea Captain's home, located in downtown Chatham. Enter through the cozy porch directly into the gourmet kitchen with a granite counter breakfast bar and café table for a total seating of 8. Down the hall there are 2 spacious living areas offering...

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

from

$300

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$300
Per month:$9,000
Pets allowed:No
Internet:Yes

Enjoy the downtown location of this Cape Cod Vacation Rental Home in the village of Chatham. Convenient to Chatham shops, restaurants, new Orpheum movie theatre and Oyster Pond. Families love the proximity to the playground, public tennis courts and Chatham Angler Baseball field...

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Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
3 Bedrooms / 3 Bathrooms / 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:Yes

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 bike ride...

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Chatham Home
2 Bedrooms / 2 Bathrooms / 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:Yes

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 where...

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Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$330

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$330 - $421
Per month:$9,900 - $12,630
Pets allowed:Yes
Internet:Yes

Pet Friendly! Cape Cod Luxury vacation condo in the heart of Chatham Village! Head up the stairs over the Chatham Beach Dog to find a lovely deck with café table and gas grill. Open the door to your little piece of heaven: the open floor plan boasts a gourmet kitchen, including...

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Chatham Home
2 Bedrooms / 1 Bathroom / Sleeps 5

from

$192

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:5
Type:Home
Per night:$192
Per month:$5,760
Pets allowed:No
Internet:Yes

Wouldn't you like to spend some time at this adorable updated Cape Cod Vacation Rental cottage in Chatham? It is in a convenient location with a path at the end of the street to Forest Beach or a short walk to Pleasant Road Beach. The bike trail is just off Rt 28 on the corner of ...

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Chatham Massachusetts Vacation Rentals - Home
1 / 19

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 9

from

$322

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:9
Type:Home
Per night:$322 - $408
Per week:$2,250 - $2,850
Pets allowed:No
Internet:Yes

RENT ME NOW ! OPEN WEEKS !        Private Home. All you need to pack are clothes. Everything is provided for that very special vacation adventure. Located in the highly sought after Sesuit Neck section of East Dennis, you will arrive for your vacation to a spacious 2500 sq....

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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, 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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