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Holiday Rentals in Chilmark

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Holiday Rentals in Chilmark

Our top choices for Chilmark holiday rentals

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

10.0 out of 10, Exceptional, (53)
"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 + Lvl2 EV charger.

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (326)
"Nice amenities. "
The Club at New Seabury

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (176)
"We really enjoyed the warm hospitality, the spacious rooms, great location right by the beach and great size pool. It’s close to downtown and walkable to a few restaurants. "
InnSeason Resorts Captain's Quarters

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (134)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is €156
includes taxes & fees
2 Sept - 3 Sept
Sea Mist Resort

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (85)
"Great stay! "
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

8.6 out of 10, Excellent, (42)
"Great place for a summer vacation"
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.2 out of 10, (24)
"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (200)
"Enjoyed our stay."
Southcape Resort Mashpee a Ramada by Wyndham

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

8.4 out of 10, Very good, (20)
"So turn key and perfect for Month, Joy is an exceptional host and I’d recommend her place anytime"
The price is €176
includes taxes & fees
21 Aug - 22 Aug
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

9.6 out of 10, Exceptional, (40)
"Fantastic beach cabin in a nice location, close to Gay Head lighthouse and several beaches, including the dog-friendly Lobsterville. Good views, plenty of land, we had a good time!"
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

Relax & Unwind this Fall, at a very private & relaxing 1 bedroom 1 bath studio

10.0 out of 10, Exceptional, (6)
Relax & Unwind this Fall, at a very private & relaxing 1 bedroom 1 bath studio

The Costal Corner - Martha's Vineyard

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was great for our golf trip. The 3 bedrooms were exceptional "
The Costal Corner - Martha's Vineyard

Walking to the beach. Bars and Restaurants.

9.6 out of 10, Exceptional, (4)
"The home was very nice and in a convenient location. Ana was very helpful and quick with communications during our stay. Would highly recommend for anyone traveling to Oak Bluffs! "
Walking to the beach. Bars and Restaurants.

Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.

10.0 out of 10, Exceptional, (28)
"We had a great trip and look forward to staying there again. Location is the best part!"
The price is €555
includes taxes & fees
17 Sept - 18 Sept
Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.

Oceanview 2 Double Bed Groundfloor Suite

10.0 out of 10, Exceptional, (1)
"Our trip was a last minute decision, and needed to stay just one night. The location, the fast response, clear instructions, cleanliness, assigned parking and pricing all came together very nicely! "
The price is €203
includes taxes & fees
2 Sept - 3 Sept
Oceanview 2 Double Bed Groundfloor Suite

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

8.8 out of 10, Excellent, (33)
"Great spot for a get away. Private with easy access to activities."
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

Private cottage nestled in center of the Vineyard

10.0 out of 10, Exceptional, (49)
"This whole experience was better than I could have imagined. The cottage was beautiful in a perfect setting. my Hosts went the extra distance. I didn't arrive until close to midnight. My hosts had left fruit, salad, yogurt and ice cream for me. Since I was unable to get a rental car this meant I had something to eat in the morning. I will definitely stay there again! "
Private cottage nestled in center of the Vineyard

In Ground Pool, A/C, 4+BR, 3BA, Wifi, Game Room. Sleeps 10-12, strong wifi

9.0 out of 10, Wonderful, (57)
"We found this property to be ideally suitable for our needs as a family and very convenient for exploring the cape! The inground pool sure came in handy and everyone had a good time! "
In Ground Pool, A/C, 4+BR, 3BA, Wifi, Game Room. Sleeps 10-12, strong wifi

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

10.0 out of 10, Exceptional, (53)
"This home serves as a lovely base while vacationing on Martha’s Vineyard. It’s an easy walk to some great places to eat, a grocery store, boutiques, and more. Plus, it’s just down the street from the Vineyard Haven ferry terminal.The host is both incredibly proactive and responsive. Stocked with all the right stuff, immaculate, and decorated with cute coastal flair, this home makes for a super comfortable stay."
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
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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Top Chilmark Hotel Reviews

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?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This holiday home rental outside of Chilmark offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Chilmark?

Choose from 74 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.