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Chilmark Holiday Rentals

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Holiday Rentals in Chilmark

Aerial view
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
10.0 out of 10, Exceptional, (33)
"Everything about this house was perfect for our visit with family on MV. It was clean, comfortable, and had all the amenities we needed for a lovely fall week on MV. The location is private and peaceful, with beautiful views. Communication with Christian was easy and accommodating. A little gem!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
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
Outdoor dining
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
10.0 out of 10, Exceptional, (157)
"Loved everything about this home! Perfect location. Fantastic views and decorated so beautifully. Would love to stay here again. Highly recommend!"
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
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Property grounds
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
10.0 out of 10, Exceptional, (11)
"All my wife's children and grandchildren gathered at this lovely home to celebrate her 70th birthday. The home and grounds/neighborhood are simply great and Thomas was a wonderful and responsive host. Since some folks stayed the whole visit and others were only with us for a long weekend, we were thrilled that the dining area accommodated our whole group when necessary, and the kitchen allowed many hands to make light work. The dining table doubled as a spot for the family to gather and...
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Fridge, microwave, oven, stovetop
Stunning East Falmouth Home w/ Pool and Central AC
10.0 out of 10, Exceptional, (7)
"Spacious, clean, loved the pool"
Stunning East Falmouth Home w/ Pool and Central AC
Fridge, microwave, oven, stovetop
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
10.0 out of 10, Exceptional, (171)
"This property is absolutely beautiful. It is tastefully redone with amazing touches that make you feel clean, welcome and comfortable! I cannot say enough about this home. We had the best stay here. The rooms were large with comfortable beds and PLENTY of extra pillows and blankets. It is the perfect house for a large family. Simple walk to Main Street / library/ huge playground. The host Roberta thought of everything you might ever need during your stay. She was responsive and kind. There...
The price is AU$873
per night
29 May - 30 May
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Property grounds
Centrally-Located New Seabury Waterfront: Week Of June 22-29 At 35% Off!!
10.0 out of 10, Exceptional, (115)
"Very nice and would stay there again"
The price is AU$1,990
per night
16 May - 17 May
Centrally-Located New Seabury Waterfront: Week Of June 22-29 At 35% Off!!
Exterior
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
9.8 out of 10, Exceptional, (63)
"Property is in a great location, walking distance to the shore and a little longer walk or short drive will get you to town with a pub and a few places to eat. Martha’s Vineyard ferry parking is less than ten minutes away with a free shuttle bus that takes you to the ferry. Regina (owner) is right next door and is very friendly and accommodating!!"
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
Iron/ironing board, WiFi, bed sheets
Romantic seaside getaway with pool & tennis courts - dog-friendly
9.8 out of 10, Exceptional, (36)
"Great location, lots of amenities - pool, fire pits, tennis courts, nearby restaurant. Communication for checking was excellent."
Romantic seaside getaway with pool & tennis courts - dog-friendly
On the beach, white sand
InnSeason Resorts Captain's Quarters
3.5 star property
9.6 out of 10, Exceptional, (142)
"We had an amazing time and stay. Just wish we had known in advance that this was a no smoking town. Not many places to smoke. But will totally come back again. Every day i went to the beach and collected the most beautiful shells."
InnSeason Resorts Captain's Quarters
Interior
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
9.6 out of 10, Exceptional, (70)
"The apartment was spotless! Open and airy. The host left excellent instructions, and a phone number if needed. We did and he responded immediately and problem resolved. I have only one suggestion. You need more than one mirror It’s located in the bathroom. Need another either in hall or bedroom I would recommend this apartment to anyone"
The price is AU$1,053
per night
16 May - 17 May
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Fridge, microwave, oven, stovetop
Beautiful bright home with firepit, deck & backyard - walk to beach
9.6 out of 10, Exceptional, (45)
"Very clean, welcoming"
Beautiful bright home with firepit, deck & backyard - walk to beach
Property grounds
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
9.6 out of 10, Exceptional, (74)
"Place was nice. Pool was the key selling point for a winter trip. Tv in every room, but I think something was wrong w the xfinity. Only master bedroom worked with Netflix to watch. That was a huge bummer. If it was warmer weather wouldn’t have been as much of an issue. They had lots of things to do for nice weather but wasn’t the time of year. House was over all nice and relaxing."
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
Fridge, microwave, oven, stovetop
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
9.6 out of 10, Exceptional, (28)
"This home away from home offers spacious bedrooms and living spaces on a nice grassy lot in a quaint neighborhood setting. Step out onto your deck and sit at the table and watch the little bunnies nibbling the grass and listen to the birds singing. Clean, well-equipped and stocked with essentials, including all linens, this place has got you covered! A bookshelf full of guides and summer reads, toys and games for the kiddos for family time indoors as well as a beach wagon loaded-up for...
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Property grounds
new listing Waterview 3BR/2BTH home in East Falmouth with lake views and access
9.6 out of 10, Exceptional, (23)
"Fantastic!"
new listing Waterview 3BR/2BTH home in East Falmouth with lake views and access
Property grounds
Last minute deal - walk to the beach - 4 bedroom - super cute!
9.6 out of 10, Exceptional, (72)
"Such an easy walk to Falmouth Heights Beach and a 5 min drive to downtown, we loved the location of this house! The house itself was large and we comfortably fit 8 adults and 2 babies. Thank you!"
Last minute deal - walk to the beach - 4 bedroom - super cute!
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
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
Breathtaking Views with Private Dock & Pool: Summer Special 40% off!
9.2 out of 10, Wonderful, (17)
"We had 3 family birthdays this week & for the 1st time in years we were all together. What made it extra special was this fantastic property & superb location. Maria was so easy to communicate with, it just made everything super smooth. When you get the weather here in the creeks and rivers it is an incredibly enjoyable place to stay, protected kayaking, peaceful yet close to the shops at Mashpee Commons for all the essentials. Thank you Maria."
Breathtaking Views with Private Dock & Pool: Summer Special 40% off!
Seasonal outdoor pool, pool cabanas (surcharge), pool umbrellas
The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (281)
"Good "
The price is AU$342
per night
28 May - 29 May
The Club at New Seabury
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See all available properties in Chilmark
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 types of properties in Chilmark you may be interested in

Porch
Summercamp
3.5 star property
9.2 out of 10, Wonderful, (589)
"Great location, clean, staff were very helpful and friendly."
The price is AU$346
per night
22 May - 23 May
Summercamp
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
Exterior
Sea Crest Beach Hotel
3.5 star property
7.8 out of 10, Good, (1001)
"We stay here regularly, but there was construction going on this time and the hot tub was also closed the whole weekend which was unfortunate. Had we known that, we may have chose to stay on different dates. Although it is off-season, there were some cleanliness features that were not up to par in both the room and around the property. "
The price is AU$292
per night
20 May - 21 May
Sea Crest Beach Hotel
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.

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.