Photo by Wen C.

Holiday Rentals in Chilmark

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Holiday Rentals in Chilmark

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
8.4 out of 10, Very good, (21)
"Wonderful place for a getaway to MV. Well appointed, comfy home with great pool. Plenty of privacy but easy to get to. Enjoyed our stay"
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Beautiful dog-friendly home with water view, balcony & washer/dryer
8.0 out of 10, Very good, (11)
"The house is tucked down a magical driveway with serene surroundings. Unfortunately, there were a few things that left us feeling a bit disappointed. It was clear we were one of the first visitors of the season. The house was quite musty, the washer was filled with water and mold, the showers were not cleaned, showing clear hard water, spider webs, and some build up. The comforter in the master was stained, including some blood. The AC on the top floor was not working. Lastly, the door handle...
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, (41)
"Beautiful and peaceful "
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Cozy efficiency apartment/heated pool
10.0 out of 10, Exceptional, (16)
"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, (298)
"The property was nice! Super location as it’s just steps away from the beach. Get to beach early or there’s no umbrellas available. They do a great job with setting up chairs on the beach. Hard workers! Beach bars are super convenient and bathrooms were clean. Tons to do all around. Nice restaurants, lots of shopping. Bummed to see some of the cute shops at marketplace aren’t there anymore. Still cute though. "
The price is €235
includes taxes & fees
29 Sept - 30 Sept
The Club at New Seabury
Sea Mist Resort by VRI Americas
3.0 star property
8.8 out of 10, Excellent, (101)
"Check in was easy and we got to check in at 3:30pm. Our room was large, kitchen, LR, 2 baths, BR and deck. It was very quiet, clean, and the bed was comfortable. No coffee is available in the room, or shampoo/conditioner. Only gripe was before leaving we got calls in the room and on our cell to get out. Check out is 10am...most are 11am. The resort was pretty much empty so it wasn't like they needed the room asap. I've never had this happen and didn't appreciate the calls. "
Sea Mist Resort by VRI Americas
InnSeason Resorts Captain's Quarters
3.5 star property
9.6 out of 10, Exceptional, (148)
"Need more comfortable chairs in tv room"
InnSeason Resorts Captain's Quarters
Coastal chic meets French Provençal in this newly renovated oceanfront home.
10.0 out of 10, Exceptional, (68)
"We loved the entire experience. Great location. Host was very responsive and helpful. House was perfect. "
The price is €985
includes taxes & fees
22 Sept - 23 Sept
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, (68)
"Great time"
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
9.2 out of 10, Wonderful, (46)
"We needed a little getaway at the end of summer and this was the perfect place! Great location! Great views! We enjoyed it very much. Photos were accurate. "
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
9.6 out of 10, Exceptional, (77)
"Great stay. Like others have said, only two towels, no beach towels, and have to deal with electrical breakers on your own. Got info for getting into place in a timely fashion but didnt get a response on a question i asked during my stay. Best view on the island. Just bring your own stuff"
The price is €640
includes taxes & fees
22 Oct - 23 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
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, (17)
"Large kitchen and living area with enough space to sleep the 12 of us. Large beautiful back deck with a nice fire pit. Great location, close to everything including our favorite Old Silver Beach and if you don’t feel like going to the beach you can float, swim or take the paddle boat on the lake right in your back yard. We would definitely stay here again!!"
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Beautiful bright home with firepit, deck & backyard - walk to beach
9.6 out of 10, Exceptional, (48)
"Great home - hope to be back again! We had a blast. "
Beautiful bright home with firepit, deck & backyard - walk to beach
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
10.0 out of 10, Exceptional, (181)
"I think this was our 7th year staying at this wonderful house. It’s become a home away from home for our family. Everything about the house and our stay was, and always is, perfect. And the property owner, Roberta, is extremely responsive and an absolute pleasure. I wish I could give it more than 5 stars! "
The price is €529
includes taxes & fees
1 Oct - 2 Oct
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
9.6 out of 10, Exceptional, (79)
"We enjoyed our stay at Kelly's place. Kelly was extremely responsive anytime I reached out with a question which was very appreciated. The location of the home is wonderful and exactly what we wanted. Highlights: quiet neighborhood, lots of space, warm + clean pond, clean pool that we could adjust temp on to be more like a hot tub or pool, comfortable beds, beautiful outdoors. We hope to return! "
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
10.0 out of 10, Exceptional, (170)
"The house was very pretty inside and out but the view was spectacular. Walking paths around the pond and directly to the beach. Great restaurants and towns to visit."
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
8.6 out of 10, Excellent, (76)
"We had a wonderful family vacation at this property. The owner was so helpful and communicative. We loved the location. We really appreciated the two minute walk to the beach and quick walk to the Poppy Market which we visited daily for morning coffees and dinner. The water views off the back patio were beautiful. Would definitely recommend! "
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
8.8 out of 10, Excellent, (25)
"Perfect space for a couple, minutes out of Edgartown in a wildlife refuge."
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
Escape on conservation land with furnished deck, pond views, sunroom, & AC
9.0 out of 10, Wonderful, (13)
"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
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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
8.4 out of 10, Very good, (21)
"Wonderful place for a getaway to MV. Well appointed, comfy home with great pool. Plenty of privacy but easy to get to. Enjoyed our stay"
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Summercamp
3.5 star property
9.2 out of 10, Wonderful, (827)
"Perfect location liked sitting on the porch for morning coffee and evening watching the activity around the marina"
The price is €196
includes taxes & fees
21 Oct - 22 Oct
Summercamp
Sea Crest Beach Resort
3.5 star property
7.8 out of 10, Good, (1000)
"Nice beachside resort. "
The price is €209
includes taxes & fees
21 Oct - 22 Oct
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 Menemsha Blues Charters, whereas Lucy Vincent Beach and Menemsha Beach are a couple of great spots to enjoy the outdoors. While here, Waskosim's Rock Reservation and Fulling Mill Brook Preserve 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.