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Compare 749 Vacation Homes in Chilmark with updated reviews, rates, and availability.

Property grounds
Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths
10.0 out of 10, Exceptional, (7)
"Beautiful home with a great view, right on the ocean. Was very quiet when we went (off season), but will definitely be renting again. Very clean, and had just about everything you would need!"
Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths
Fridge, microwave, oven, stovetop
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
8.2 out of 10, Very Good, (24)
"Upon entering the property, everything was very clean and welcoming. The rooms were spacious and comfortable. It felt like home. We would definitely book this property again."
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
3 bedrooms, WiFi, bed sheets
Escape on conservation land with furnished deck, pond views, sunroom, & AC
8.8 out of 10, Excellent, (9)
"Very nice property. Excellent location!"
Escape on conservation land with furnished deck, pond views, sunroom, & AC
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Property grounds
Adorable waterfront home w/ boat access & a three-season sunroom
9.2 out of 10, Wonderful, (15)
"On the whole, we enjoyed our stay. Had informed Vacasa that we wouldn’t arrive in Falmouth until midnight 4/25 (as we picked up relatives at Logan Airport), but it hadn’t been forwarded: the sloping entry to the cottage was pitch-dark! In the morning we found garbage cans tipped over, & trash strewn all around the yard —the same thing happening the second night (both times we had to clean up a mess). We requested an hour’s leeway for departing 4/27, which was to have been relayed to local owner;...
Adorable waterfront home w/ boat access & a three-season sunroom
Aerial view
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
10.0 out of 10, Exceptional, (35)
"Christian was a terrific host. Very accommodating and quick to respond. The location was private, serene, with beautiful views. The house was clean, simply designed, and everything I needed was available. Perfect all around. Thank you, Christian!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Outdoor dining
SUMMER RETREAT AWAITS YOU
9.0 out of 10, Wonderful, (14)
"This was our second time staying in Mashup Village. The house was cozy and clean. Had everything we needed for a few nights away at the beach. The house was less than a 5 minute walk to the which was great for our 2 boys."
SUMMER RETREAT AWAITS YOU
Beach nearby
Private cottage nestled in center of island, access to Lambert's Cove beach
10.0 out of 10, Exceptional, (26)
"Host was exceptional. Very quiet and secluded. Central on the island for all points of interest. The cottage was private and well appointed."
Private cottage nestled in center of island, access to Lambert's Cove beach
TV, books
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
10.0 out of 10, Exceptional, (2)
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Outdoor dining
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
10.0 out of 10, Exceptional, (158)
"We had a great vacation dispite the weather. The property could not have been nicer!"
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Fridge, microwave, oven, stovetop
Stunning East Falmouth Home w/ Pool and Central AC RPAM038
10.0 out of 10, Exceptional, (7)
"Spacious, clean, loved the pool"
Stunning East Falmouth Home w/ Pool and Central AC RPAM038
Beach
Cozy Massachusetts Escape w/ Patio, Near Beaches!
Cozy Massachusetts Escape w/ Patio, Near Beaches!
Fridge, microwave, oven, stovetop
Renovated townhome with pool & 3 tennis courts - golfing & beaches nearby
9.4 out of 10, Exceptional, (28)
"Good"
Renovated townhome with pool & 3 tennis courts - golfing & beaches nearby
Private kitchen | Fridge, microwave, oven, stovetop
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
9.0 out of 10, Wonderful, (37)
"Very clean and updated property! Conveniently located near the water. Comfortable place for us to rest and give my daughter/husband their space. Recommend this place and look forward to hopefully staying again. My only suggestion is to add dimmable lighting. We felt on stage in the living/kitchen area, bedroom. It would be nice to turn down bathroom light during the night."
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
Property grounds
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
6.0 out of 10, (19)
"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
TV
Perfectly located duplex with comfy layout & beach gear - steps from Main Street
10.0 out of 10, Exceptional, (3)
"lovely"
Perfectly located duplex with comfy layout & beach gear - steps from Main Street
Interior
Walk your way into Vineyard Haven from Walker Way!
10.0 out of 10, Exceptional, (31)
"The property was perfect for our weekend getaway for a family wedding. The weather was terrible so we didn’t get to enjoy the cute deck! The string lights made it seem so inviting. The kitchen had everything we needed for 3 nights and the house had a great floorplan for us! We loved that you could walk to VH and hear the ferry whistle blow while in the house. The check in process couldn’t have been easier and the house felt very private. Thanks for a shirt but sweet stay!"
Walk your way into Vineyard Haven from Walker Way!
Outdoor dining
Inviting home near town and the beach with fast WiFi, fireplace, & private W/D
6.6 out of 10, (7)
"Stained curtains, worn furnishings, moldy smell offset the nice kitchen and great location."
Inviting home near town and the beach with fast WiFi, fireplace, & private W/D
Smart TV
3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights
9.6 out of 10, Exceptional, (19)
"The house is in the middle of everything Falmouth. We had a nice stay!"
3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights
Property grounds
Unique Up-Island Home
9.6 out of 10, Exceptional, (31)
"All the amenities that everyone needs."
Unique Up-Island Home
Sun loungers, beach towels
Megansett Beach Cottage
10.0 out of 10, Exceptional, (18)
"The house was perfect for our "girls" weekend. It is very clean with bath/kitchen updates and the surrounding neighborhood is quiet and peaceful. Very easy to walk to the beach and a short drive to the nearby village. The Host was very easy to reach with questions."
Megansett Beach Cottage
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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.

Other property types in Chilmark

View from property
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
8.4 out of 10, Very Good, (18)
"Overall my friends and I have come twice to the Noyes house and are planning to come back next year. As long as you’re comfortable not staying near the main towns, it’s an ideal location - close to the markets and stores of west tisbury, several of the best beaches on the island (Lucy Vincent and Aquinnah in particular), the Chilmark general store, and some of the best farms like beetlebung. The house is something between rustic and luxury, which is deal for a group of friends. It’s not a big...
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Aerial view
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
10.0 out of 10, Exceptional, (35)
"Christian was a terrific host. Very accommodating and quick to respond. The location was private, serene, with beautiful views. The house was clean, simply designed, and everything I needed was available. Perfect all around. Thank you, Christian!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Fridge, microwave, oven, stovetop
Beautiful dog-friendly home with water view, balcony & washer/dryer
9.4 out of 10, Exceptional, (8)
"Only reason I didn’t give a five for location is that it was sort of far away from most things, but it was a beautiful location out in the woods. The house was lovely and the views were awesome. Would recommend!"
Beautiful dog-friendly home with water view, balcony & washer/dryer
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.

Chilmark Vacation Homes information

Number of reviews
418
Accommodation
749 Vacation Homes
Lowest Price
Highest Price

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