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Chilmark Vacation Rentals

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Vacation Rentals in Chilmark

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

10.0 out of 10, Exceptional, (52)
"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)
"A great unique and quiet place, very close to Boston."
The price is CA $381
CA $436 total
includes taxes & fees
Sep 2 - Sep 3
The Club at New Seabury

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (176)
"Just a quick weekend away. Great location for beach lovers. Also excellent retaurants "
InnSeason Resorts Captain's Quarters

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (133)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is CA $220
CA $252 total
includes taxes & fees
Sep 2 - Sep 3
Sea Mist Resort

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (98)
"Great location! Nice property! "
The price is CA $434
CA $497 total
includes taxes & fees
Aug 19 - Aug 20
Beachside Village Resort

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 CA $160
CA $310 total
includes taxes & fees
Aug 19 - Aug 20
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

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.

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

Renovated 1-bedroom apartment in Downtown Falmouth Located Right on Main Street

2.0 star property
9.0 out of 10, Wonderful, (2)
"I would 100% recommend this apartment! My friends and I had the best experience. The host was so friendly and made himself available for us via text and in person whenever we needed. The listing aligns perfectly with the actual apartment. The apartment was extremely clean and shampoo conditioner etc were provided for us as well as extra bedding. The building is super easy to access with the instructions provided and the location is amazing as it is right on Main Street in Falmouth! Overall we...
Renovated 1-bedroom apartment in Downtown Falmouth Located Right on Main Street

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 CA $275
CA $873 total
includes taxes & fees
Sep 17 - Sep 18
Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.

Breathtaking Views with Private Dock & Pool!

9.2 out of 10, Wonderful, (25)
"Great location!! Awesome stay"
Breathtaking Views with Private Dock & Pool!

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

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)
"We had a wonderful stay! The place was clean, cute, and very conveniently located. Would definitely return!"
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

9.6 out of 10, Exceptional, (69)
"Clean property, great location"
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

Walking-distance to town, shops, restaurants & ferry!

10.0 out of 10, Exceptional, (18)
"I rented this for my staff, and they said it was the best place they have stayed on Martha's Vineyard."
Walking-distance to town, shops, restaurants & ferry!

4-bedroom house in lovely Mashpee 5 minutes from beach

10.0 out of 10, Exceptional, (1)
"We came for the weekend. It was super clean, and well furnished. It was surprising to me that we were his first VRBO stay. "
4-bedroom house in lovely Mashpee 5 minutes from 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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Top Chilmark Hotel Reviews

Frequently asked questions

Can I find vacation rentals in Chilmark?

Yes, there are vacation rentals in Chilmark near Chilmark Chocolates, or you can select a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals that Chilmark has to offer?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This vacation home rental near Chilmark offers a patio, a barbecue grill, 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 vacation rentals are there in Chilmark?

Choose from 74 Expedia vacation rentals in Chilmark for a memorable vacation.

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 vacation rental in Chilmark like?

A vacation rental is a private property where you can stay for a long or short time in Chilmark. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.