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Chatham Cape Cod Vacation Rentals

There are plenty of activities and things to do in and around Chatham for vacationing families.
For beach goers there are Cockle Cove and Ridgevale Beaches. Golfers will enjoy the scenic, nine hole Chatham Seaside Links and the 36 hole Captains Golf Course is in nearby Brewster. Day trips for whale watching and deep sea fishing are also close by. A branch of the  Cape Cod Rail Trail begins in Chatham and extends to Dennis at one end and Wellfleet at the other. Baseball fans will enjoy watching a Chatham Anglers game against an opposing team of the Cape Cod Baseball Leage. There are many family and fine dining restaurants to choose from and an assortment of antique and speciality shops. Stop in town for a bite to eat or a beverage after a day on the beach or out on a boat.
For more activities, please visit our Things To Do page.

Search Results

Found 11 properties

Beautifully Maintained 3BR Colonial Close to Forrest Beach

$2150/week

South Chatham | #1577
3 BR | 2 Baths | Sleeps 8

This rental is a comfortable 3 bedroom, 2 bath that sleeps 8. It sits on a pretty lot with a big backyard just 7/10th of a mile to Forest Beach in Chatham.

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Cape 3BR Home Close to Pleasant Bay

$1500-2000/week

Chatham | #1978
3 BR | 2.5 Baths | Sleeps 8

This 3 bedroom cottage is the perfect location for your family stay in Chatham. You can't beat the location less than a mile away from Jackknife Beach on Pleasant Bay, 2.5 miles to downtown Chatham and Oyster Pond Beach.

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Coastal Cottage With Deeded Access To South Beach

$2500-3200/week

Chatham | #2141
3 BR | 3 Baths | Sleeps 8

Spend your vacation by the beach! Spacious Cape style home offers 2 twins, a king and 2 double beds. 2 family rooms that open out onto the back deck to spread out, relax and enjoy the warm breezes of Cape Cod.

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Cozy South Chatham Vacation Cottage

$2350-2750/week

South Chatham | #2079
4 BR | 2 Baths | Sleeps 8

This cozy South Chatham vacation cottage is located in a seaside neighborhood, close to the Chatham Beaches on Nantucket Sound and enticing local restaurants and shops.

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Cute Cottage - Half Mile to Nantucket Sound!

$1375/week

South Chatham | #1976
2 BR | 1 Baths | Sleeps 6

Perfect for a relaxing vacation. Located in a quiet location in South Chatham, only ½ mile to Nantucket Sound.

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Explore Chatham's Nantucket Sound Beaches!

$800-1150/week

South Chatham | #2037
2 BR | 2 Baths | Sleeps 6

Conveniently located in South Chatham. Minimum 2 Week Rentals Only, this lovely Townhouse is close to some of Chatham's best swimming beaches.

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Lovely Chatham Home Near the Bike Trail

$1500-1950/week

South Chatham | #1524
3 BR | 2 Baths | Sleeps 6

Enjoy this 3-bedroom, 2 bath contemporary Chatham home just minutes from the Cape Cod Rail Trail for great cycling and 1 mile to the beautiful beaches on Nantucket Sound.

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Meticulous Cape Home- Walk to Ridgevale Beach- Central Air

$4500/week

Chatham | #2142
4 BR | 3 Baths | Sleeps 10

Sophisticatedly furnished and well maintained 4BR/3BA Cape style home accessible to Ridgevale Beach. This home is located less than .4 miles Chathams’ finest beaches!

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North Chatham - Charming "Stones Throw"

$1500-3000/week

Chatham | #2130
4 BR | 2 Baths | Sleeps 8

Located outside of downtown Chatham sits this charming four bedroom home, known as Stones Throw. This property features great amenities such as central air conditioning, high speed wireless internet, and flat screen TVs in every bedroom.

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Pet friendly home with central air

$1850/week

Chatham | #1998
4 BR | 2 Baths | Sleeps 8

This adorable PET FRIENDLY cape style home is located on a peaceful, residential, dead end road, close to two fresh water ponds and just a short drive to Pleasant Bay!

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Ryder Cove Waterviews- Steps To Neighborhood Beach On Harbor

$6500/week

North Chatham | #2131
4 BR | 4 Baths | Sleeps 8

Exquisite four bedroom home located in a prestigious North Chatham neighborhood! Offering plenty of room to spread out, this lovely home features upscale furnishings in multiple living areas, plus water views of Ryder's Cove from almost every room.

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