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Vacation Homes in Chilmark

Our top choices for Chilmark vacation homes

Maushop - 6 Hammock Pond Rd

9.0 out of 10, Wonderful, (34)
"The beach access very nice nice for early morning or evening walks - quiet and private neighborhood. The 2 bedroom unit was comfortable and met our needs."
Maushop - 6 Hammock Pond Rd

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

10.0 out of 10, Exceptional, (182)
"The best and the most relaxing stay in Cape Cod. Close to ocean, breathtaking views , beautiful and very comfortable house. "
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C

West Falmouth Cottage in the Heart of This Historic Village.

10.0 out of 10, Exceptional, (55)
"Great location, comfortable and perfect for my family of four. "
West Falmouth Cottage in the Heart of This Historic Village.

Your Oasis Awaits

9.6 out of 10, Exceptional, (43)
"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

Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach

5.8 out of 10, (6)
"The living room was moldy, the door doesn’t lock, the insects were in every room; including the bed, the kitchen tools were rusty, the floors were dirty, the place is a mess. The post states a gas grill; there’s only a charcoal grill without any charcoal, the post states resident beach parking pass; there was none, the post states a queen size bed; there wasn’t one. The kitchen floor was completely stripped of tile. Overall the house was dirty and a complete waste of money. The only nice thing...
Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach

Maushop Property - First Time Available

10.0 out of 10, Exceptional, (42)
"Property is very quiet and only a few minutes walk to the beach! The pictures of the beach and stairs can be a bit misleading as these are for the entire property, not this house. The beach did look nice and had plenty of room for everyone staying here. Would definitely recommend for a couple or a family with kids. Plenty to do and lots of great restaurants within a half hour drive "
Maushop Property - First Time Available

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

10.0 out of 10, Exceptional, (179)
"Great location and host was easy to talk to. The house was nice and plenty spacious enough for 2 families. Great central location to beaches and restaurants. "
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!

10.0 out of 10, Exceptional, (62)
"The most magical place, thank you for the prefect stay."
Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!

Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts

9.8 out of 10, Exceptional, (78)
"Central property with all essentials!"
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts

Cozy cottage 3/4 mile from Oak Bluffs harbor

9.8 out of 10, Exceptional, (48)
"Stayed here with 3 friends as we were running the marathon. Better than the photos! So cute, everything was thoughtfully set up, we had anything we needed and having a washer dryer was a huge bonus! Flexible check in as well. Secluded, but easily walkable to many great places to eat and shop. Would 100% stay here again, highly recommend."
Cozy cottage 3/4 mile from Oak Bluffs harbor

Maushop - Perfect for your Vacation

9.8 out of 10, Exceptional, (34)
"Perfect fall getaway"
Maushop - Perfect for your Vacation

Quaint,,,Quiet..up island feel yet a short walk to town and harbor

9.8 out of 10, Exceptional, (92)
"Awesome, fun place. Has everything you need for a great Vineyard stay!"
Quaint,,,Quiet..up island feel yet a short walk to town and harbor

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

6.6 out of 10, (29)
"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

Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

10.0 out of 10, Exceptional, (109)
"Great outdoor spaces. Loved the kayaks, beach and fire pit. Our 2 year old grandson loved the outdoor shower. Our dog had a ball chasing squirrels in the fenced backyard. We would definitely stay again. Close to everything in Falmouth including Woodneck beach, our low tide favorite. "
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

9.8 out of 10, Exceptional, (23)
"We had a great week staying at this property. It's well maintained and had plenty of room for a family getaway to the Cape. Steps away from the beach, this property is well taken care of and had everything we needed for a comfortable stay. This would be our first choice for any future trips to the Cape."
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS

9.6 out of 10, Exceptional, (31)
"This home was absolutely beautiful. In a great location to get anywhere in the island. The host was extremely helpful when needed. I would one hundred percent recommend this place to anybody! "
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS

Sanctuary House: An ocean-view farmhouse retreat

10.0 out of 10, Exceptional, (34)
"Property was as presented and the attention to detail throughout the house to ensure we enjoyed the stay was noticed and appreciated! Will definitely recommend Dan and Havens Sanctuary Farm to others!"
Sanctuary House: An ocean-view farmhouse retreat

The quintessential MV home. Now booking for 2026!

9.8 out of 10, Exceptional, (53)
"Just a quick 4 minute drive to downtown. Listing was accurate and place was clean!"
The quintessential MV home. Now booking for 2026!

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

9.6 out of 10, Exceptional, (92)
"Overall, it was a wonderful stay... very peaceful. Thank you so much. I would consider even buying it if it were for sale (depending on price of course)."
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!

Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach

10.0 out of 10, Exceptional, (87)
"Very nice house and property in the quietest part of the island. Great thing is that it is only 2.5 miles away from the beach!!"
Martha's Vineyard Cozy Getaway Near Picturesque Philbin 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

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Chilmark Vacation Homes information

Number of reviews
1,194
Accommodation
980 Vacation Homes
Lowest Price
Highest Price