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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, (45)
"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, (307)
"accommodation was good but cleanliness could have been better. Not bad but some areas needed more attention. Good restaurant and bar service on Thursday. No restaurant available on Saturday."
The price is €172
includes taxes & fees
26 Dec - 27 Dec
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."
The price is €157
includes taxes & fees
6 Jan - 7 Jan 2025
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 €952
includes taxes & fees
20 Jan - 21 Jan 2025
Coastal chic meets French Provençal in this newly renovated oceanfront home.

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.

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 €962
includes taxes & fees
31 Dec - 1 Jan 2025
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

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

Sea Mist Resort by VRI Americas

3.0 star property
8.8 out of 10, Excellent, (113)
"We loved having two full bathrooms and kitchen "
Sea Mist Resort by VRI Americas

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!

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!

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

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

9.6 out of 10, Exceptional, (76)
"We loved our 2 day stay in Falmouth. We came up for an October wedding. The VRBo was 3 minutes walking distance from the beautiful beach. There was plenty of room and the house was very clean. We would love to come up again and would definitely recommend staying here! "
Last minute deal - walk to the beach - 4 bedroom - super cute!

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

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, (189)
"This was our second stay at Roberta’s lovely home. The house is in a great location (very nice area, close to everything) and is very comfortable. There were 5 of us and there was plenty of room. The kitchen is very nice and was great for preparing Thanksgiving dinner- plenty of seating in the dining area. The house was very clean, nicely decorated, with a great backyard. Roberta is a great host- very responsive and helpful- she had the fridge stocked with water and cream for coffee as well...
The price is €510
includes taxes & fees
5 Jan - 6 Jan 2025
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

new listing Waterview 3BR/2BTH home in East Falmouth with lake views and access

9.6 out of 10, Exceptional, (26)
"We enjoyed relaxing on back porch listening to the birds in the morning and the quiet nights so very peaceful! Our host was great to give us recommendations for the area. Since it was our first time in Cape, it made things a little easier in deciding where to eat and places to visit. Thanks again!!"
new listing Waterview 3BR/2BTH home in East Falmouth with lake views and access
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

Holiday Inn Cape Cod-Falmouth, an IHG Hotel

3.0 star property
7.6 out of 10, Good, (774)
"I have stayed here many times through different ownership and it has always been safe, quiet and comfortable. There is evidence of wear and tear that could use and upgrade but nothing that affects the comfort of the stay."
The price is €102
includes taxes & fees
30 Dec - 31 Dec
Holiday Inn Cape Cod-Falmouth, an IHG Hotel

Sea Crest Beach Resort

3.5 star property
8.2 out of 10, Very good, (30)
"Room was fantastic. Staff was super friendly. Great location on the ocean. Just a great experience.."
The price is €175
includes taxes & fees
5 Jan - 6 Jan 2025
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 68 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 Menemsha Beach and Lucy Vincent 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.