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Vacation Homes in Chilmark

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

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

6.2 out of 10, (24)
"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Cape beach house steps to beach, a short walk to town & AC
Dining

Cape beach house steps to beach, a short walk to town & AC

10.0 out of 10, Exceptional, (5)
Cape beach house steps to beach, a short walk to town & AC
Private cottage nestled in center of the Vineyard
Beach nearby

Private cottage nestled in center of the Vineyard

10.0 out of 10, Exceptional, (49)
"This whole experience was better than I could have imagined. The cottage was beautiful in a perfect setting. my Hosts went the extra distance. I didn't arrive until close to midnight. My hosts had left fruit, salad, yogurt and ice cream for me. Since I was unable to get a rental car this meant I had something to eat in the morning. I will definitely stay there again! "
Private cottage nestled in center of the Vineyard
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
Terrace/patio

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

8.8 out of 10, Excellent, (33)
"Great spot for a get away. Private with easy access to activities."
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
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.
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Outdoor dining

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

8.4 out of 10, Very Good, (39)
"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
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.
Popponesset, Exclusive, 3-Bdrm, 4-Bths, Sleeps 6, pool, hot tub, firepit, & A/C
Smart TV, fireplace, books

Popponesset, Exclusive, 3-Bdrm, 4-Bths, Sleeps 6, pool, hot tub, firepit, & A/C

10.0 out of 10, Exceptional, (81)
"Loved the house. Enjoyed our walk to the beach "
Popponesset, Exclusive, 3-Bdrm, 4-Bths, Sleeps 6, pool, hot tub, firepit, & 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
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!!
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 modern Falmouth home near the beach
Outdoor dining

Coastal modern Falmouth home near the beach

10.0 out of 10, Exceptional, (2)
"We have stayed in many vacation rentals and this was by far the nicest home we have ever stayed in. We had an absolutely wonderful stay at this beautiful coastal Falmouth home. The location is absolutely perfect and the town of Falmouth is adorable. From the moment we arrived, Jon and Libby made us feel so welcome. They are truly outstanding hosts. The house was spotless, bright, and beautifully decorated, creating such a cozy and inviting atmosphere. Every detail was thoughtfully taken care of,...
Coastal modern Falmouth home near the beach
Enjoy the off season on Cape Cod in a Charming 3-BR house in pleasant E Falmouth
Smart TV

Enjoy the off season on Cape Cod in a Charming 3-BR house in pleasant E Falmouth

9.6 out of 10, Exceptional, (5)
Enjoy the off season on Cape Cod in a Charming 3-BR house in pleasant E Falmouth
Last minute deal - walk to the beach - 4 bedroom - super cute!
Beach nearby, sun loungers

Last minute deal - walk to the beach - 4 bedroom - super cute!

9.6 out of 10, Exceptional, (81)
"This was such a perfect spot to spend time with friends before our wedding! Loved being near the beach and plenty of space for all our guests. Thank you so much! "
Last minute deal - walk to the beach - 4 bedroom - super cute!
New Seabury home, spacious deck & outdoor shower
TV

New Seabury home, spacious deck & outdoor shower

9.2 out of 10, Wonderful, (14)
"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
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
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
Fridge, microwave, oven, stovetop

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

7.6 out of 10, Good, (4)
"We loved the location. The outdoor shower was a hit with the kids."
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
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
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, (26)
"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."
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
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

Green Harbor Waterfront Lodging

Green Harbor Waterfront Lodging

10/10 Excellent
"The place is incredibly clean staff very helpful a/c great , shower fantastic only thing is it dated but well kept we enjoy our stay will be back and recommend to friends"
felix 2-night trip
Posted 3 days ago
Green Harbor Waterfront Lodging