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Holiday Rentals in Chilmark

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Holiday Rentals in Chilmark

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
8.6 out of 10, Excellent, (22)
"We didn't realize how beautiful and unique the architecture of this residence was before we arrived. It is a gorgeous place and we were please by the cleanliness and simplicity of it. "
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Beautiful dog-friendly home with water view, balcony & washer/dryer
7.8 out of 10, Good, (14)
"A Vacasa managed property that has everything you could want. We stayed 4 nights with our whole family and our small dog. It had everything we could want and we enjoyed ourselves. Recently redone, with good fit and finish and places to hang cook and relax off a dirt road that is well situated. Our only comments would be that there were some things needing fixing like the grill handle, lights not in sockets, and general disarray of bedding and supplies in the closets. While clean and fresh...
Beautiful dog-friendly home with water view, balcony & washer/dryer
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
10.0 out of 10, Exceptional, (44)
"We were in town for a wedding in Chilmark and the property was exactly what we needed!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Cozy efficiency apartment/heated pool
9.8 out of 10, Exceptional, (17)
"What a wonderful gem in the woods of Chilmark. The pool is the icing on the cake. Ronnie was such a wonderful host! Hope to return in the fall, but definitely again in the future."
Cozy efficiency apartment/heated pool
The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (304)
"will definitely go back again .. awesome place! "
The price is €160
includes taxes & fees
25 Nov - 26 Nov
The Club at New Seabury
InnSeason Resorts Captain's Quarters
3.5 star property
9.8 out of 10, Exceptional, (154)
"Very clean property. Beach just across street. Great views."
InnSeason Resorts Captain's Quarters
Coastal chic meets French Provençal in this newly renovated oceanfront home.
10.0 out of 10, Exceptional, (72)
"The home and views were stunning! Clean, comfortable, and plenty of space for everyone. Easy communication with the host. We had a lovely stay!"
The price is €1,136
includes taxes & fees
13 Dec - 14 Dec
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Beachside Village Resort by VRI Americas
3.0 star property
9.2 out of 10, Wonderful, (86)
"A very nice place and wonderful location. You can see sunrise from this property. Staff are nice and friendly. A great experience!"
Beachside Village Resort by VRI Americas
Sea Mist Resort by VRI Americas
3.0 star property
8.8 out of 10, Excellent, (111)
"We loved having two full bathrooms and kitchen "
Sea Mist Resort by VRI Americas
Quiet duplex by the beach, short walk to Falmouth Village, 1 GB Internet.
9.8 out of 10, Exceptional, (70)
"Between the beautifully landscaped yard and the proximity to the ocean, this is a fabulous place! We love walking to the ocean for our am and pm walks, The Shining Sea Bike trail is also very close and just a joy! Property owners were great to work with. Definitely will stay here next year. Thanks for a great stay!!! "
Quiet duplex by the beach, short walk to Falmouth Village, 1 GB Internet.
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
9.0 out of 10, Wonderful, (53)
"Great location, clean, everything was as described in the listing. Upgraded furniture and linens would have yielded 5 stars."
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
Beautiful bright home with firepit, deck & backyard - walk to beach
9.6 out of 10, Exceptional, (50)
"Great space and location."
Beautiful bright home with firepit, deck & backyard - walk to beach
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
8.6 out of 10, Excellent, (79)
"Great location but the place was dirty. Need a better cleaning service. "
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Breathtaking Views with Private Dock & Pool!
9.2 out of 10, Wonderful, (21)
"Great location. Loved the deck overlooking the water, the dock, the kayaks and the pool right next to the house. We mostly stayed around the house and the bay. Local free beach was close by with no one there on cooler windy days. Host, Maria, was very responsive to questions we had."
Breathtaking Views with Private Dock & Pool!
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. "
The price is €1,078
includes taxes & fees
30 Nov - 1 Dec
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
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
10.0 out of 10, Exceptional, (68)
"We attended a wedding Friday night. The location of the house was within 1 mile. Great location. The property was beautiful and we couldn’t be happier with our stay. "
Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
10.0 out of 10, Exceptional, (173)
"What a wonderful stay on the Cape in a beautiful setting that was so quiet and peaceful, we both unwound and relaxed from our very busy lives. The house was warm and comfortable and the proximity to the beach was excellent. We especially loved the hot tub on the cool evenings. Big shout out to the property managers, Paul and Katy! THANK YOU and we look forward to future stays."
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Escape on conservation land with furnished deck, pond views, sunroom, & AC
9.0 out of 10, Wonderful, (14)
"House is great and has everything. The one remote to operate the a/c in one of the upstairs bedrooms needed new batteries (we think). Also we think the entry lock battery is low as it kept going out on us mid code. We wrote the Vacasa people and they wanted us to buy new batteries. NO. It up tk the property manager to take care of this."
Escape on conservation land with furnished deck, pond views, sunroom, & AC
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
10.0 out of 10, Exceptional, (188)
"The house was as advertised! Spacious, clean, comfy beds and close to town and beach. Very nice stay. We would definitely rent again! Thank you!"
The price is €560
includes taxes & fees
25 Nov - 26 Nov
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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Other types of properties in Chilmark you may be interested in

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
8.6 out of 10, Excellent, (22)
"We didn't realize how beautiful and unique the architecture of this residence was before we arrived. It is a gorgeous place and we were please by the cleanliness and simplicity of it. "
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Mansion House Inn And Spa
3.5 star property
9.4 out of 10, Exceptional, (1021)
"We love the Mansion House!"
The price is €171
includes taxes & fees
24 Nov - 25 Nov
Mansion House Inn And Spa
Sea Crest Beach Resort
3.5 star property
8.0 out of 10, Very good, (24)
"Places is very clean and organized. Everything is violently available right in the building."
The price is €200
includes taxes & fees
1 Dec - 2 Dec
Sea Crest Beach Resort
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.

Frequently asked questions

Can I find holiday rentals in Chilmark?

Yes, there are holiday rentals in Chilmark close to Chilmark Chocolates, or you can select a more secluded option if you're looking for a relaxing stay. Chilmark is known for its beaches and wineries. Make sure you have time to check out the festivals and local tours during your trip.

What are some of the best holiday rentals that Chilmark has to offer?

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks: This highly rated holiday home rental in Chilmark is located near the beach, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chilmark?

Choose from 69 Expedia holiday rentals in Chilmark for a memorable holiday.

What’s there to see and do in Chilmark?

Family-friendly attractions include Chilmark Chocolates and Fulling Mill Brook Preserve, whereas Lucy Vincent Beach and Menemsha Beach are a couple of great spots to enjoy the outdoors. While here, Chilmark Town Hall and Chilmark Public Library are other places worth a visit.

What’s a holiday rental in Chilmark like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chilmark. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.