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Compare 717 Vacation Homes in Chilmark with updated reviews, rates, and availability.

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Access to pond with dock and paddle boat!

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

10.0 out of 10, Exceptional, (22)
"Thank you Thomas and Julie, had a great week, so convenient and Welcoming. "
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Exterior

Historic Oak Bluffs home, short walk to town, beach, and harbor.

9.6 out of 10, Exceptional, (28)
"We enjoy it all. "
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Gorgeous Spacious Victorian Cape Code Beach View Retreat
Exterior

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Gorgeous Spacious Victorian Cape Code Beach View Retreat
Large New Seabury Home with Heated Pool and Hot Tub
The perfect backyard for summer fun. A brand new hot tub and pool await.

Large New Seabury Home with Heated Pool and Hot Tub

10.0 out of 10, Exceptional, (39)
"We stayed for a week over the Christmas holidays. The house easily accommodated our group of eight people and one dog. We enjoyed the easy walk to the National Wildlife Refuge and a quick drive for winter beach walks. We enjoyed spending time with a roaring fire and a few dips in the hot tub. Tori was very responsive to the couple of issues that arose. "
Large New Seabury Home with Heated Pool and Hot Tub
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Exterior

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

10.0 out of 10, Exceptional, (56)
"This house is the perfect destination for a group get together. It is an easy walk to the ferry so cars are not needed on the island. we had a great time and are looking forward to our next stay."
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches
Cathedral Cape located in the highly desirable Katama area of Edgartown

Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches

10.0 out of 10, Exceptional, (89)
"My friends and I stayed at this wonderful property for my birthday celebration. We had a wonderful time. This is the best supplied Vrbo house I have ever stayed in and I have stayed in many. Korrie is a perfect host and her house is amazing. Great for a family with kids in that there are 2 separate fun areas for kids and grownups! We played ping pong and put puzzles together. The first floor bedroom is perfect for those who don't love stairs. I rate this house as 5/5 stars! Thank you...
Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches
Martha’s Vineyard 4BR Home-Katama Edgartown South Beach Area-open Mem Day wknd
2 Crafts Field Way, Edgartown (outside shower) (9 beach chairs in shed)

Martha’s Vineyard 4BR Home-Katama Edgartown South Beach Area-open Mem Day wknd

9.8 out of 10, Exceptional, (49)
"We enjoyed our stay at this property. We didn’t spend a lot of time at the house but it certainly served its purpose. I think it would be a great place to stay in the summer with its proximity to the beach and bike path. The only minus was having to drive the long way around because of the horrible condition of the main dirt road. All that said, I would certainly stay there again!"
Martha’s Vineyard 4BR Home-Katama Edgartown South Beach Area-open Mem Day wknd
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

7.4 out of 10, Good, (3)
"We had a wonderful early-June weekend stay at this charming house minutes walk from town. Highlights were reading on the rocking chair on the deck and playing games in the screened-in porch. Everything looks just like in the listing - charming, warm, like staying at your grandpa's beach house. There were a few bumps - the listed dryer was in a locked shed, a faucet wasn't working - but our sense was this is a new listing and details are still being ironed out. None of that interfered with our...
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
Walk To Town - Beautiful Edgartown House
Living room

Walk To Town - Beautiful Edgartown House

9.8 out of 10, Exceptional, (52)
"We had a wonderful stay in this home. Perfectly appointed and you can’t beat the location. Especially loved the outdoor shower!"
Walk To Town - Beautiful Edgartown House
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Exterior

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (74)
"Beautiful home and views"
The price is SAR 1,594
SAR 4,022 total
includes taxes & fees
7 Feb - 8 Feb
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Rear view of the house with deck, patio, grill, adirondacks,two tables 12 seats.

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10.0 out of 10, Exceptional, (190)
"Once again, we enjoyed our family Christmas on the Cape in our favorite area. This house has everything you will need for a comfortable stay. The house is immaculate and completely stocked. The beds are extremely comfortable, there is plenty of room for our entire family to enjoy themselves and Roberta was so easy to communicate with if needed. We will definitely stay here again. "
The price is SAR 675
SAR 1,945 total
includes taxes & fees
31 Jan - 1 Feb
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
The Beach Estate, Panoramic Ocean Views, 5700 sqft
Exterior

The Beach Estate, Panoramic Ocean Views, 5700 sqft

10.0 out of 10, Exceptional, (5)
"This house is spectacular and we cannot wait to rent again. There’s nothing to complain about except we didn’t rent it longer. "
The price is SAR 2,626
SAR 6,565 total
includes taxes & fees
12 Feb - 13 Feb
The Beach Estate, Panoramic Ocean Views, 5700 sqft
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
Exterior

Beachfront On John's Pond, Indoor HEATED Pool, and Dock!

9.6 out of 10, Exceptional, (82)
"Wonderful property on the pond. We had a great time. Would rent again. "
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana
18 Menemsha Road, Popponesset 14 x 28, heated in-ground saltwater pool

Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana

10.0 out of 10, Exceptional, (70)
"Loved the house. Enjoyed our walk to the beach "
Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana
Beach front, fenced yard, pet friendly, central air, fire pit, kayaks, hot tub
View from Deck overlooking the pond

Beach front, fenced yard, pet friendly, central air, fire pit, kayaks, hot tub

10.0 out of 10, Exceptional, (94)
"Great location, even with the weather being awful we were able to utilize some of the amenities. "
Beach front, fenced yard, pet friendly, central air, fire pit, kayaks, hot tub
Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom
Living area

Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom

8.0 out of 10, Very Good, (7)
"Cute property in a great location. The neighborhood felt very safe and it was a perfect spot for my family. House was clean and the space was great. "
Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom
SPECTACULAR SUMMER RETREAT
Exterior

SPECTACULAR SUMMER RETREAT

9.6 out of 10, Exceptional, (25)
"This house felt like a home away from home! Everything we needed was readily available, and the host couldn’t be nicer. The cottage itself is adorable, and really makes you feel like you’re in a true beach town. The easy walk to the beach was unparalleled, and the beach itself was a dream. This is definitely a place we’ll definitely come back to - and we highly recommend it to all!"
SPECTACULAR SUMMER RETREAT
Country Farmhouse, Old Vineyard charm, New Amenities, Central AC, 2 King beds.
East side of house.

Country Farmhouse, Old Vineyard charm, New Amenities, Central AC, 2 King beds.

9.6 out of 10, Exceptional, (4)
"Nice and Quiet place. Would book again!"
Country Farmhouse, Old Vineyard charm, New Amenities, Central AC, 2 King beds.
Steps to 3 Falmouth Beaches in our 6+bedroom with oversized outdoor shower
Exterior

Steps to 3 Falmouth Beaches in our 6+bedroom with oversized outdoor shower

Steps to 3 Falmouth Beaches in our 6+bedroom with oversized outdoor shower
Elisa's Cottage - Your Family Vacation Destination
Exterior

Elisa's Cottage - Your Family Vacation Destination

10.0 out of 10, Exceptional, (5)
"We chose Elisa’s Cottage for a weekend visit with friends who live in the area. We could not have made a better choice. Andrew has thought of everything guests might need. The house is immaculately clean and thoughtfully decorated. It is spacious and comfortable. The location is quiet and private. Andrew met us at check in to make sure we had everything we needed. The goodies in the welcome basket were a nice touch! Thank you Andrew’"
Elisa's Cottage - Your Family Vacation Destination
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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Other property types in Chilmark

The Club at New Seabury
Outdoor pool

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (311)
"Tired unit. Primary bath water closet leaked around base. No soap or paper towels. "
The price is SAR 512
SAR 586 total
includes taxes & fees
13 Feb - 14 Feb
The Club at New Seabury
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Exterior

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (74)
"Beautiful home and views"
The price is SAR 1,594
SAR 4,022 total
includes taxes & fees
7 Feb - 8 Feb
Coastal chic meets French Provençal in this newly renovated oceanfront home.
InnSeason Resorts Captain's Quarters
Aerial view

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (158)
"This is the 4th time I've stayed at an Inn Season resort in Falmouth. There are 3 properties available and they are all quite nice. This visit was at Captains Quarters overlooking Heights Beach. It was a winter weekend with a steady fall of very fine snow. The accommodations are always spot on. It was picturesque and a perfect weekend getaway to relax and unwind. "
The price is SAR 671
SAR 768 total
includes taxes & fees
31 Jan - 1 Feb
InnSeason Resorts Captain's Quarters
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.