Chilmark, MA Cottage Rentals from $620

A dock with boats, a small wooden structure, and a forested shoreline.

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In two weeks

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Our top choices for Chilmark cottages

1. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

East Falmouth

"We had a wonderful stay at this charming New England home. The house was spotless, beautifully maintained, and full of character. It had all the comforts we needed, inviting spaces to relax in after exploring the area. The location was perfect—close to local shops, scenic spots, and great dining. Our host was friendly, responsive, and made us feel right at home. We honestly couldn’t have asked for a better experience, and we look forward to returning."

Shaun G.

$552 nightly

Oct 5 - Oct 6

Total with taxes and fees

2. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

East Falmouth

$542 nightly

Oct 5 - Oct 6

Total with taxes and fees

3. Charming cottage overlooking the bay in Padanaram Village.

Dartmouth

Judith M.

$466 nightly

Sep 20 - Sep 21

Total with taxes and fees

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Top Chilmark Hotel Reviews

Hampton Inn by Hilton New Bedford/Fairhaven

8/10 Good

"The facility was excellent and we had a nice stay"

Faraway Martha's Vineyard

8/10 Good

"A few smaller items that made the stay slightly questionable, no elevator bags had to be carried. Not much to do about that in an historical building, but it's a note for guests. I would expect a notch better, especially when coming to bedding. The bed was comfortable, but I would expect down pillows and blanket at this price point. The record player was a lovely touch. Parking was challenging, but again, historical town we must make compromises. Wonderful shower towels, GREAT pool and hot tub area. The location of the hotel is / was supreme. Only coffee offered in the lobby, no inroom machine, and no option of a latte, or capp in the hotel or lobby, only in adjacent restaurant. (Loud bathroom fan, bug in room, a little mildew build up on the shower grout, definite degradation happening on plumbing fixtures. At this price point, should be better)"

Harbor View Hotel

10/10 Excellent

"We always enjoy our stays at the Harbor View. The rooms are terrific and beautifully appointed, and the staff is consistently helpful and friendly. The front veranda, with its sweeping views of Edgartown Lighthouse, the Atlantic Ocean, and Chappaquiddick, is truly delightful. The on-site Bettini Restaurant is another fabulous amenity—convenient, inviting, and absolutely delicious. You simply can’t go wrong booking a stay at the Harbor View!"

The Coonamessett

8/10 Good

"We really enjoyed our stay at the Coonamessett. We chose it because we were planning to visit Martha’s Vineyard, and its location was very convenient for getting to Woods Hole, where we caught our ferry. It was also a convenient distance from the ferry parking lot. Tish at the front desk was patient, welcoming, and extremely helpful throughout our stay. The property itself is charming, with beautiful grounds and a lovely, quaint feel. Our room had a cozy cottage feel and was quite spacious. The shower was clean and well stocked, and the two AC units worked very efficiently. We also appreciated having two TVs—one in the sitting area and one in the bedroom. There was plenty of closet space, which conveniently also housed the refrigerator and a collapsible luggage bench. A few things to note: there is no tea/coffee service or microwave in the room. We stayed in Room 8, which did not really have a water view, despite the property being advertised as having water views. Rooms 30 and possibly Room 1 appear to have better water views. Breakfast was fresh and delicious, although the offerings were the same throughout our stay. That’s fairly typical of hotels, but given that the Coonamessett is on the higher end, a little more variety would have been a nice touch. Overall, we had a very enjoyable stay. The charming setting, comfortable accommodations, convenient location, and wonderful hospitality made it a pleasant experience."

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Chilmark Cottages information

Number of reviews
Accommodation	149 Cottages
Lowest Price	$620
Highest Price	$620

Frequently asked questions

How much do cottages in Chilmark cost?

You can expect to pay between $620 and $620 per night for cottages in Chilmark. No matter your budget, a fantastic stay is just a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Why book your cottage in Chilmark with Expedia?

We think that vacations should be a walk in the park, so if you're searching for cottages in Chilmark at an affordable price, Expedia can help. Keep the budget under control and pick a low-cost option far away from the city rush, or book a 5-star cottage to treat your loved ones.

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With Expedia's filter tool, sourcing cheap cottages in Chilmark is a snap. To find properties that'll make your wallet smile, narrow down your search by star rating, budget and amenities.

What is there to do in Chilmark near my cottage?

Whatever you're interested in, Chilmark has lots of things to keep you entertained. Menemsha Beach, Lucy Vincent Beach and The Yard are on many visitors' trip plans. Don't forget about Chilmark Chocolates, Waskosim's Rock Reservation and Fulling Mill Brook Preserve either. With Expedia's hotel deals in Chilmark, you'll be able to discover more neat attractions like these with the money you save.

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Things to do in Martha's Vineyard

Room 1

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Our top choices for Chilmark cottages

1. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

2. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

3. Charming cottage overlooking the bay in Padanaram Village.

Find vacation rentals that suit your style

Top Chilmark Hotel Reviews

Hampton Inn by Hilton New Bedford/Fairhaven

ShoreWay Acres Inn & Cape Cod Lodging

Faraway Martha's Vineyard

Summercamp

Harbor View Hotel

Mansion House Inn And Spa

MV Surfside Hotel

The Coonamessett

The Cape Club Resort

Find out more about Chilmark

Chilmark Cottages information

Frequently asked questions

Explore a world of travel with Expedia

Search Chilmark Cottages

Check prices for these dates

Our top choices for Chilmark cottages

1. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

2. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

3. Charming cottage overlooking the bay in Padanaram Village.

Find vacation rentals that suit your style

Top Chilmark Hotel Reviews

Hampton Inn by Hilton New Bedford/Fairhaven

Find out more about Chilmark

Chilmark Cottages information

Frequently asked questions

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