Chatham Vacation Rentals, Homes, & More

1-50 of 222 Chatham Rentals

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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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Chatham Massachusetts Vacation Rentals - Home
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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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 - $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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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 / 22

Chatham Home
4 Bedrooms / 2 Bathrooms / 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 / 24

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$325

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$325 - $471
Per month:$9,750 - $14,130
Pets allowed:Yes
Internet:No

Pet Friendly! Located in a prime in- town location this Cape Cod Vacation Rental Cottage complex is just steps to the Mill Pond (a saltwater inlet of Nantucket Sound) in Chatham' s Old Village and a few blocks to the Beautiful Lighthouse Beach. This desirable and newly renovated...

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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
4 Bedrooms / 4 Bathrooms / Sleeps 10

from

$600

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$600
Per month:$18,000
Pets allowed:Yes
Internet:Yes

On the Water! With Central Air and Wireless Internet- Pet Friendly too (for Dogs only- ask your rental specialist for details). This Cape Cod Vacation Rental home in North Chatham has expansive views of Pleasant Bay from both a lower and upper deck, both living areas, the dining...

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Chatham Massachusetts Vacation Rentals - Home
1 / 38

Chatham Home
5 Bedrooms / 4 Bathrooms / 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
1 / 21

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$245

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$245 - $407
Per month:$7,350 - $12,210
Pets allowed:No
Internet:No

Cute and Coastal and plenty of room for 3 couples or 2 families. This Cape Cod Vacation Rental in Chatham has an open floor plan with 3 bedrooms on the main floor and a fully finished lower level game/family room with extra sleeping. Deeded access to Oyster Pond at the end of the ...

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Chatham Massachusetts Vacation Rentals - Home
1 / 17

Chatham Home
1 Bedroom / 1 Bathroom / Sleeps 4

from

$200

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Home
Per night:$200
Per month:$6,000
Pets allowed:Yes
Internet:No

Pet Friendly! Located in a prime in- town location this Cape Cod Vacation Rental Cottage complex is just steps to the Mill Pond (a saltwater inlet of Nantucket Sound) in Chatham' s Old Village and a few blocks to beautiful Lighthouse Beach. This desirable and newly renovated...

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Chatham Massachusetts Vacation Rentals - Home
1 / 34

Chatham Home
4 Bedrooms / 4 Bathrooms / 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
1 / 3

Chatham Home
6 Bedrooms / 7 Bathrooms / 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
1 / 23

Chatham Home
5 Bedrooms / 3 Bathrooms / Sleeps 9

from

$965

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:9
Type:Home
Per night:$965
Per week:$6,750
Pets allowed:No
Internet:No

$5, 900 PRIME SUMMER WEEKLY RATEThis 5 bedroom home offers impressive views of the Atlantic Ocean and a short walk across the street to Lighthouse Beach. This updated home has been renovated with the goal of maintaining much of the original charm of the colonial era. However, you...

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Chatham Massachusetts Vacation Rentals - Home
1 / 23

Chatham Home
3 Bedrooms / 2 Bathrooms / 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
1 / 26

Chatham Home
3 Bedrooms / 4 Bathrooms / 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
1 / 20

Chatham Home
6 Bedrooms / 7 Bathrooms / 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

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 Massachusetts Vacation Rentals - Home
1 / 20

Chatham Home
4 Bedrooms / 5 Bathrooms / Sleeps 10

“ 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 / 17

Chatham Home
4 Bedrooms / 3 Bathrooms / 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
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...

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Chatham Massachusetts Vacation Rentals - Home
1 / 20

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: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 / 22

Chatham Home
3 Bedrooms / 3 Bathrooms / 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

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

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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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 / 22

Chatham Home
4 Bedrooms / 3 Bathrooms / Sleeps 10

from

$428

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$428
Per month:$12,840
Pets allowed:Yes
Internet:No

$3, 000 PRIME SUMMER WEEKLY RATEThis home has 4 bedrooms and has a classic Cape Cod decor. All of the modern amenities are included: AC units in all bedrooms, WiFi, flat screen TV with digital cable, washer/dryer, and all the kitchen necessities. The small yard is fenced in so...

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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 / 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 / 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 / 20

Chatham Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$914

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$914
Per month:$27,420
Pets allowed:No
Internet:No

Luxury 4 bedroom, 3. 5 bath Cape Cod Vacation Rental home tucked up off of Bridge Street, in Chatham. Privately placed on just over a half acre of land in a peaceful setting, yet just a hop, skip and a jump away you can find Lighthouse beach! It’ s an easy walk into the...

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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:No

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...

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Chatham Massachusetts Vacation Rentals - Home
1 / 7

Chatham Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$257

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$257 - $260
Per month:$7,710 - $7,800
Pets allowed:No
Internet:No

Private, Family Ranch Style Riverbay home in Chatham for your Cape Cod Vacation located on a dead end road. As you enter the through the front door you will find comfortable seating in the living room with a flat screen TV. There is a hallway leading you to the bedrooms on the left....

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Chatham Massachusetts Vacation Rentals - Home
1 / 21

Chatham Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$372

/ night

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

Come and relax in your home away from home. This Newer Cape Cod Vacation Home Rental in Chatham is now available for summer rental. Enjoy this well maintained home, with open floor plan for easy summer living. Central A/C and Wifi too. Step up onto the charming porch with seating...

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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
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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
1 / 20

Chatham Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$564

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$564
Per month:$16,920
Pets allowed:No
Internet:No

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
1 / 15

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:No

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...

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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 Massachusetts Vacation Rentals - Home
1 / 24

Chatham Home
3 Bedrooms / 3 Bathrooms / Sleeps 7

from

$325

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:7
Type:Home
Per night:$325 - $557
Per month:$9,750 - $16,710
Pets allowed:No
Internet:No

Location – Location- Location! Luxury Chatham Vacation Rental home with 3 bedroom, 3. 5 bath in the heart of Chatham and sleeps 7. Whether you Enjoy cocktails on the traditional front porch, read a good book in the cozy sun room, eat outdoors on the mahogany deck or take...

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Chatham Massachusetts Vacation Rentals - Home
1 / 16

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 Massachusetts Vacation Rentals - Home
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Chatham Home
5 Bedrooms / 2 Bathrooms / Sleeps 11

from

$608

/ night

Email Owner
Bedrooms:5
Bathrooms:2
Sleeps:11
Type:Home
Per night:$608
Per week:$4,250
Pets allowed:No
Internet:No

$4, 250 PRIME SUMMER WEEKLY RATEThis antique home is located in the Sears Point section of Chatham a stone' s throw from Stage Harbor. This classic Chatham home sleeps 10, has a 2 minute walk to Stage Harbor and access to a private tennis court (available for use 10am- 5pm)....

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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...

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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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