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Vacation Homes in Chilmark

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.0 out of 10, (22)
"There were times when the shower in the master bathroom only emitted cold water. The water spigot in the tubs would not turn completely off in bathroom in the hallway. I had trouble with the lockbox. Maybe add more specific directions. It would have been helpful to know that MV transit bus was available at the intersection of the street and County Road."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Maushop - 6 Hammock Pond Rd

9.0 out of 10, Wonderful, (32)
"Very clean, comfortable furniture, close walk to beach. We had a great visit!"
Maushop - 6 Hammock Pond Rd

Maushop Property - First Time Available

10.0 out of 10, Exceptional, (41)
"Great spot, we loved it!"
Maushop Property - First Time Available

Popponesset-New rental-3 Bedrooms, close to beaches, A/C and so much more.

10.0 out of 10, Exceptional, (11)
"Clean, well maintained home in a great location"
Popponesset-New rental-3 Bedrooms, close to beaches, A/C and so much more.

Spacious home in central location with beautiful patio, pool table, W/D, & AC

10.0 out of 10, Exceptional, (1)
"We loved our stay. This is the first time I have rented a house without a prior review. So glad we did! The house seemed brand new or very recently remodeled. The pool table and media area downstairs made the rainy day we had on the island a great one. We had a party of seven and plenty of space to spread out and relax. It was easy to walk to town but we also rented bikes to get around. I would highly recommend this home to anyone looking for a relaxing stay on Martha's Vineyard."
Spacious home in central location with beautiful patio, pool table, W/D, & AC

Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C

6.2 out of 10, (17)
"This property has not been well cared for or cleaned. Arrived to a very musty/moldy smell, trash outside, the walls were streaked with dead bug guts and then the stove didn't work!! It was a step above camping. You get what you pay for!"
Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

8.6 out of 10, Excellent, (38)
"Close to the beach , clean and a wonderful Vineyard stay"
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Waterfront Home w/ Guest Cottage

10.0 out of 10, Exceptional, (1)
"I lined the view from the home and the safety in the area! Overall, great place for a big family !"
Waterfront Home w/ Guest Cottage

Victorian cottage overlooking downtown Oak Bluffs and the Harbor.

2.0 star property
10.0 out of 10, Exceptional, (1)
"Nice nostalgic home Needs minor work (Toilet seats)(Middle room mirror )AC "
Victorian cottage overlooking downtown Oak Bluffs and the Harbor.

Charming 3-bedroom house with a pool, AC, WiFi in pleasant East Falmouth

9.4 out of 10, Exceptional, (3)
"Really beautiful place with a lot of space and a very helpful host"
Charming 3-bedroom house with a pool, AC, WiFi in pleasant East Falmouth

Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.

10.0 out of 10, Exceptional, (15)
"had a great weekend at the house and the area... might be back again"
Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.

New Seabury home, spacious deck & outdoor shower

9.2 out of 10, Wonderful, (13)
"My adult family members stayed at this home during a family gathering. The space was clean and had ample space for all. "
New Seabury home, spacious deck & outdoor shower

West Falmouth Cottage in the Heart of This Historic Village.

10.0 out of 10, Exceptional, (51)
"Great location, comfortable and perfect for my family of four. "
West Falmouth Cottage in the Heart of This Historic Village.

Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

9.6 out of 10, Exceptional, (52)
"This was a lovely home in a very nice location"
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

Spacious colonial home close to town with AC, porches, & W/D

10.0 out of 10, Exceptional, (3)
"We had such a great stay here. Very clean and super close to town. We would definitely stay here again. Thanks!"
Spacious colonial home close to town with AC, porches, & W/D

Your Oasis Awaits

9.6 out of 10, Exceptional, (40)
"We had a great stay. Nice and close to the beach so my mid 80’s mom could even walk back and forth. and the raw bar on property was the perfect place for an easy meal. Would happily stay again."
Your Oasis Awaits

Cape Escape: Beaches and Bonfires with King bed

10.0 out of 10, Exceptional, (2)
"Everything was in great condition and we had everything we need and more. We were all very happy with the accommodations. Easy check in/out."
Cape Escape: Beaches and Bonfires with King bed

Charming Home with Deck, Screened Porch, Private Balcony, Near Beaches

9.4 out of 10, Exceptional, (60)
"Loved the area and the peacefulness"
Charming Home with Deck, Screened Porch, Private Balcony, Near Beaches

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

10.0 out of 10, Exceptional, (2)
"Mike & Olya's house is even more beautiful in person, both inside and out.The house is equipped with everything needed for a peaceful stay. The décor and contemporary style made us want to live there — very tasteful.Check-in and check-out were easy to access. We were authorized to enter the house starting at 4 p.m.The cleaning crew was delayed by just a few minutes (maybe 5 minutes), and I immediately received a message saying I had been refunded for the inconvenience. Although such a gesture...
$620 nightly
The price is $710
Aug 25 - Aug 26
Total includes taxes and fees
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

The Field House - Peaceful Martha’s Vineyard Escape with Serene Field Views

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had such a wonderful stay at this house! The layout was perfect — all the bedrooms were spacious and comfortable for our whole group. We especially loved the bright, open living space and the kitchen, which made gathering together so easy. The house was clean and full of natural light.The back deck with its patio seating was the perfect spot for an early morning coffee, and the large open field was great for a soccer game with our group. Plus, the hot tub was an amazing bonus. It was so much...
The Field House - Peaceful Martha’s Vineyard Escape with Serene Field Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chilmark Hotel Reviews