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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Chilmark Vacation Homes

Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Outdoor dining

Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C

10.0 out of 10, Exceptional, (178)
"The property had all the amenities and features to make guests feel right at home. We appreciated all the details in the decor and we appreciated the suggestions for local restaurants. TheTheviewwdrdreadream!amademade"
The price is CA $484
CA $1,227 total
includes taxes & fees
Sep 2 - Sep 3
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Maushop - Perfect for your Vacation
Property grounds

Maushop - Perfect for your Vacation

9.8 out of 10, Exceptional, (30)
"Perfect fall getaway"
Maushop - Perfect for your Vacation
Beach Lovers Paradise! Cozy 3 bedroom home steps from the beach.
Exterior

Beach Lovers Paradise! Cozy 3 bedroom home steps from the beach.

9.8 out of 10, Exceptional, (7)
"Wonderful beach property. Clean home, comfortable beds and close to restaurants."
Beach Lovers Paradise! Cozy 3 bedroom home steps from the beach.
Dream vacation in our 4-Bedroom newly-renovated house 2.5 miles from the ocean.
Property grounds

Dream vacation in our 4-Bedroom newly-renovated house 2.5 miles from the ocean.

10.0 out of 10, Exceptional, (27)
"Very warm and comfortable stay with ample space and a massive backyard."
Dream vacation in our 4-Bedroom newly-renovated house 2.5 miles from the ocean.
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (198)
"As always, lovely home. Perfect place."
The price is CA $319
CA $816 total
includes taxes & fees
Sep 11 - Sep 12
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Dining

Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

9.6 out of 10, Exceptional, (40)
"Fantastic beach cabin in a nice location, close to Gay Head lighthouse and several beaches, including the dog-friendly Lobsterville. Good views, plenty of land, we had a good time!"
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Walking to the beach. Bars and Restaurants.
Paper towels

Walking to the beach. Bars and Restaurants.

9.6 out of 10, Exceptional, (4)
"The home was very nice and in a convenient location. Ana was very helpful and quick with communications during our stay. Would highly recommend for anyone traveling to Oak Bluffs! "
Walking to the beach. Bars and Restaurants.
2 Mi to Public Beach Access! Cape Cod Family Home
Fridge, microwave, stovetop, dishwasher

2 Mi to Public Beach Access! Cape Cod Family Home

2 Mi to Public Beach Access! Cape Cod Family Home
Family-Friendly Tisbury Escape - Walk to Town
Interior

Family-Friendly Tisbury Escape - Walk to Town

9.8 out of 10, Exceptional, (20)
"We were surprised by the amount of wild turkeys in the area, but other than that we really enjoyed our stay."
Family-Friendly Tisbury Escape - Walk to Town
Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel crib

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

10.0 out of 10, Exceptional, (85)
"Great stay! "
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Waterfront Home w/ Guest Cottage
Smart TV

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
4-bedroom house in lovely Mashpee 5 minutes from beach
Beach

4-bedroom house in lovely Mashpee 5 minutes from beach

10.0 out of 10, Exceptional, (1)
"We came for the weekend. It was super clean, and well furnished. It was surprising to me that we were his first VRBO stay. "
4-bedroom house in lovely Mashpee 5 minutes from beach
Sanctuary House: An ocean-view farmhouse retreat
Property grounds

Sanctuary House: An ocean-view farmhouse retreat

10.0 out of 10, Exceptional, (31)
"This property is as advertised. A perfect mix between old architecture and modern amenities. The water view faces west, so it’s a great place to relax after a day of adventure on the island and watch the sunset. Hosts were responsive and accommodating. Highly recommend. "
Sanctuary House: An ocean-view farmhouse retreat
West Falmouth Cottage in the Heart of This Historic Village.
Beach towels

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.
Quintessential waterfront cottage with screened porch - steps to Waquoit Bay
Property grounds

Quintessential waterfront cottage with screened porch - steps to Waquoit Bay

9.0 out of 10, Wonderful, (19)
"The architecture, the location on the estuary, and the view are outstanding! It is very private, but conveniently close to many Cape Cod attractions."
Quintessential waterfront cottage with screened porch - steps to Waquoit Bay
Best Kept Secret Retreat for Adults with Water & Golf Course Views!
Terrace/patio

Best Kept Secret Retreat for Adults with Water & Golf Course Views!

10.0 out of 10, Exceptional, (37)
"The home was beautiful and very well appointed. Easily accommodated our group of 8 adults with room to spare. Minor complaint is that there could’ve been a few more towels available, but the washer and dryer took care of that."
Best Kept Secret Retreat for Adults with Water & Golf Course Views!
Spacious colonial home close to town with AC, porches, & W/D
TV, DVD player, books

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

10.0 out of 10, Exceptional, (5)
Spacious colonial home close to town with AC, porches, & W/D
WOW! Still Available Last Min - Walk to Beach & Martha's Vineyard Ferry!
Outdoor dining

WOW! Still Available Last Min - Walk to Beach & Martha's Vineyard Ferry!

10.0 out of 10, Exceptional, (13)
"Had a wonderful time at this property. Very clean and well maintained. Close walk to the beach. Nice deck and back yard. Great for a family vacation! Thank you Nicole!"
WOW! Still Available Last Min - Walk to Beach & Martha's Vineyard Ferry!
Charming Home with Deck, Screened Porch, Private Balcony, Near Beaches
Terrace/patio

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

9.4 out of 10, Exceptional, (61)
"Loved the area and the peacefulness"
Charming Home with Deck, Screened Porch, Private Balcony, Near Beaches
The Field House - Peaceful Martha’s Vineyard Escape with Serene Field Views
Exterior

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location, walking distance to the fairgrounds, well appointed home, great house for our family. Large great room with windows to view the amazing property . The best outdoor shower I’ve ever been in."
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

Sea Crest Beach Resort

Sea Crest Beach Resort

10/10 Excellent
"Beautiful place to stay "
Stephanie 2-night trip
Posted 21 hours ago
Sea Crest Beach Resort