Chatham Vacation Rentals by Owners in Massachusetts, MA

Search our Chatham Massachusetts vacation rentals for vacation rental homes, villas, condos, apartments, chalets, cabins, and townhomes all offered directly from their owner/manager!

Chatham Massachusetts (MA) Vacation rentals by owner are private vacation rentals homes, villas, condos, apartments, chalets, cabins, and lodgings all available to you at a tremendous value. Please click on any of the Chatham Massachusetts (MA) listings for vacation rentals and contact information.

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Chatham Skyline Drive - hilltop getaway
"RENTALS ARE FOR 1 WEEK MINIMUM" - Soaring high above the rest of Chatham, the Eagle home is located at the highest point of the great hills of Chatham above Lovers Lake. What looks like a quaint one floor cape style home from the front is actually a lovely four bedroom two story modern home built o View more...

Great Gatsby
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 Scott Filtzgerald and himself a famous writer and poet.

The Our Great Gatsby sits on 1.3 acres in chatham overlooking Nantucket So View more...

Charming Cape Cod/ Chatham Beach House
A long awaited comfortable vacation awaits you at this recently rennovated cozy three bedroom near Chatham's most sought after family beach featuring all new bedding, new flooring, and a large kitchen. Bed linens are provided at no additional charge. Bathrooms and kitchen have been recently re View more...

Chatham Vacation Rental Home
Immaculate, bright, 3 Bedroom 1 ½ Bath, future retirement home. We are situated on a quiet cul-de-sac within comfortable walking distance to Main Street, Chatham baseball, several restaurants, Chatham Fish Pier, the town landing known as Cow Yard, Chatham Seaside Links Golf Course, 2 live theaters a View more...

New 5 Bedroom Luxury Home
Home built on over 1 acre wooded lot & abuts conservation/town watershed land for added privacy. Only a 5-7 minute walk from our backyard to a clean freshwater pond with sandy beach. Safe cul-de-sac street. Easy 5 minute drive to popular oceanside Hardings Beach on Nantucket Sound. Just blocks away View more...

Cozy Condo On The Beach . . .
''Cozy Condo on the Beach'' is a wonderful and immaculately-maintained beach condo with plenty of charm and location, location, location ... walk to 3 spectacular beaches just minutes away!!! No need to worry about packing the car, beach fees, parking, or traffic - just relax, pack a picnic and walk View more...

Chatham Village
Walk to Oyster Pond which is less than 1/2 mile away for swimming or boating. Also walk to Chatham Village for shopping, restaurants, theater, or see Chatham's finest baseball team, the Chatham A's. In-town location close to everything. Sleeps 10 people. One bedroom with a king, one bedroom with a q View more...

Chatham Vacation Rental Home

This comfortable home is perfect for an extended family vacation.

Living spaces include a great room, a living room and a family room. Wonderful views of Bucks Creek and Nantucket Sound.

Private association area with dock and picnic facilities. Beautiful sunsets. Salt water canoeing and View more...

Cape Cod Cottage
This is an ideal retreat for a couple or small family. We have many extras to make your stay enjoyable, including beach gear, games, books, dvds, and numerous everyday conveniences of home. The sunny back deck is a nice spot for an afternoon barbecue, and a two minute bicycle ride will take you to t View more...

CHATHAM VACATION RENTALS

House - 4 Bedrooms, 2.5 Baths, Sleeps 8

House - 9 Bedrooms, 4 Baths, Sleeps 18

Cottage - 3 Bedrooms, 1.5 Baths, Sleeps 6

House - 3 Bedrooms, 1.5 Baths, Sleeps 7

House - 5 Bedrooms, 2.5 Baths, Sleeps 10

Condo - 2 Bedrooms, 2 Baths, Sleeps 6

House - 3 Bedrooms, 1.5 Baths, Sleeps 10

House - 4 Bedrooms, 2.5 Baths, Sleeps 10

Cottage - 1 Bedrooms, 1 Baths, Sleeps 4