Photo by Wen C.

Search Cottages in Chilmark

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Compare 123 Cottages in Chilmark with updated reviews, rates, and availability.

Martha's Vineyard Getaway Cottage

10.0 out of 10, Exceptional, (2)
"Bright, open, clean & cozy. Will return and love the year round option."
Martha's Vineyard Getaway Cottage

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

8.6 out of 10, Excellent, (79)
"Great location but the place was dirty. Need a better cleaning service. "
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Chappy cottage with private beach

10.0 out of 10, Exceptional, (14)
"This cottage was the perfect little getaway for our family to base our first visit on Chappy. We loved being able to walk to the beach and appreciated the cleanliness of the cottage as well as its charm. "
Chappy cottage with private beach

One Bedroom Private Cottage on Large Quiet Property.

9.6 out of 10, Exceptional, (4)
"I kind of don't want to leave a good review because it will likely result in this property becoming too hard to book. jk. Seriously, everything about my experience was beyond excellent from the booking process to meeting the owners. The pictures honestly do not do it justice. It is a beautiful cottage that is far enough away from the main house to give you all the privacy one may need/want. It is in walking distance to the Vineyard Haven ferry dock and the retail in that area. The owners were...
One Bedroom Private Cottage on Large Quiet Property.

Cozy Beach Cottage

10.0 out of 10, Exceptional, (41)
"We (a party of 3 lifelong friends!) loved this little tucked away cottage. Despite the bad weather cards we were dealt with, (a lot of rain and wind) we easily walked to the Campground and marvelled at the uniqueness of the gingerbread cottages and found some good rainy day hang-out's that I wasn't aware of (especially loved Behind The Bookstore & ventured out on a little bit on a rainy night to listen to live music at Nonan's) The check-in was super easy and we took advantage of the outdoor...
Cozy Beach Cottage

3 Bedroom Cottage just steps to Private Beach! Pet Friendly!

9.6 out of 10, Exceptional, (38)
"We had an awesome time at the cottage. It’s a quick walk to the neighborhood beach that is very clean. Beautiful area and the neighbors always smiled and waved as we went by. The house was fully equipped and had everything we needed and more and was clean. We only had to buy food- all soaps and supplies were provided which was nice. The owners Matt and Carly were very responsive and friendly and gave us some great recommendations for food (Turk’s is a must!) and activities. "
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!

Martha's Vineyard 3BR, Pets Ok, 10 Min Walk to Beach or Shops!

9.6 out of 10, Exceptional, (68)
"Was exactly what I expected for our stay on the Island. I grew up on Cape Cod and looking forward to a cozy cottage on the island. The property mgr also lives on the property but I only saw her once when I communicated that the coffee maker broke and was promptly replaced with a new one. Short drive or pleasant walk to downtown Edgartown with its restaurants and shops. Love the outside shower. Was there in September so the beaches are everywhere. Great farms on the island so it's easy and fun...
Martha's Vineyard 3BR, Pets Ok, 10 Min Walk to Beach or Shops!

12 VINEYARD VIEW - FULLY RENOVATED

9.8 out of 10, Exceptional, (39)
"We had such an amazing time staying here! The location is perfect and has amazing ocean views right from the house. Everything was super clean and well maintained. We will definitely be coming back! "
12 VINEYARD VIEW - FULLY RENOVATED

Cozy Family Cottage Circuit Ave OB Walk to Everything

2.0 star property
Cozy Family Cottage Circuit Ave OB Walk to Everything

Cape Cod Cottage steps from Private Beach

10.0 out of 10, Exceptional, (32)
"Property was great. Small but we were out a lot. Great location and ownner was very helpful and responsive"
Cape Cod Cottage steps from Private Beach

★The Islander | Steps From Water, Fire Pit, AC★

10.0 out of 10, Exceptional, (44)
"I was travelling with my 3 sisters from Canada heading towards Martha's Vineyard for a sister's reunion. We all appreciated the cleanliness and the attention to detail. The space was well appointed. The fridge ice maker did not work well so having some ice cube trays would have been helpful. I highly recommend The Islander."
★The Islander | Steps From Water, Fire Pit, AC★

Cozy New TimberFrame Vineyard Haven!

10.0 out of 10, Exceptional, (19)
"As advertised. Photos are accurate, as is description. Short walk to town/supermarket, cafes and more. Accommodations are clean, well-kept, and basically brand new. Thanks! Brett Star"
Cozy New TimberFrame Vineyard Haven!

Cozy cottage w/ remodeled kitchen - less than a mile from Woods Hole Ferry

8.0 out of 10, Very Good, (28)
"We had a great time staying in Woods Hole while I was doing some work on sabbatical. It was a great location, and we lucked out with the weather too. Walking distance to the village and the beach, and very quiet neighborhood."
Cozy cottage w/ remodeled kitchen - less than a mile from Woods Hole Ferry

Charming/CozyBeachCottage-Please note rental details prior to booking. Thank You

9.8 out of 10, Exceptional, (19)
"Cozy little cottage on the beach lots of memories from my husband’s childhood. Lovely stay."
Charming/CozyBeachCottage-Please note rental details prior to booking. Thank You

Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

6.2 out of 10, (17)
"We did not stay. Place was a dump No one has called us We are not paying It is illegal not to have carbon / smoke detectors We went to condos at new seabury"
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

Cozy Lakeside Cottage Just Steps To The Beach

10.0 out of 10, Exceptional, (5)
"Beautiful area. Just a little confusion about access to the beach/lake. Otherwise house was very clean. "
Cozy Lakeside Cottage Just Steps To The Beach

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

9.6 out of 10, Exceptional, (64)
"Great property in great location on Cape Cod. 30 min drive for ferry to Nantucket. 2 minute walk to Beach within neighborhood. Cozy and quiet. Would not hesitate to stay again. "
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

Cozy, clean, relaxing beach cottage awaits you!!

10.0 out of 10, Exceptional, (34)
"Dominant house in photo is not rental. House obsequred by tree is the rental. Not enough hanging space. Single room in left house is part of rental."
Cozy, clean, relaxing beach cottage awaits you!!

1 Bedroom Guest Cottage With Water View

7.6 out of 10, Good, (27)
"It was an enjoyable place to stay in a convenient location. It’s a small, modest cottage next to the hosts who were very friendly, available, helpful and extremely accommodating. We recommend staying here and would stay here again."
1 Bedroom Guest Cottage With Water View

Cozy East Falmouth Cottage on the Seacoast Shores

2.0 out of 10, (1)
"When we arrived the house was visibly not cleaned. Perishables and half eaten food were left in the fridge, linens were visibly soiled, bathroom was dirty and owners toiletries, underwear and clothing were left in the bureau in the main bedroom. The owner was very responsive and said he would take money off to make up for it, but we still spent our first day there cleaning and laundering all of the linens and towels. We used the outdoor shower and mostly hung out on the screen porch which was...
Cozy East Falmouth Cottage on the Seacoast Shores
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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Other property types in Chilmark

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

8.6 out of 10, Excellent, (22)
"We didn't realize how beautiful and unique the architecture of this residence was before we arrived. It is a gorgeous place and we were please by the cleanliness and simplicity of it. "
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

Beautiful dog-friendly home with water view, balcony & washer/dryer

7.8 out of 10, Good, (14)
"A Vacasa managed property that has everything you could want. We stayed 4 nights with our whole family and our small dog. It had everything we could want and we enjoyed ourselves. Recently redone, with good fit and finish and places to hang cook and relax off a dirt road that is well situated. Our only comments would be that there were some things needing fixing like the grill handle, lights not in sockets, and general disarray of bedding and supplies in the closets. While clean and fresh...
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, (45)
"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 + Lvl 2 EV charger.
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

How much do cottages in Chilmark cost?
Prices for cottages in Chilmark range between and per night. No matter your budget, you’ll find the perfect place to soak up nature’s beauty. 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 a getaway should be simple, so if you’re searching for cottages in Chilmark at the perfect price, Expedia can help. Keep the budget in check and pick a thrifty option far away from the downtown buzz, or splurge on an upmarket cottage to spoil the ones you love most.
How can I find cheap cottages in Chilmark?
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