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Compare 129 Cottages in Chilmark with updated reviews, rates, and availability.

Cape Cod Holiday Estates, a VRI resort
Property grounds
Cape Cod Holiday Estates, a VRI resort
3.0 star property
9.6 out of 10, Exceptional, (120)
"Nice & clean. The only complaint Would be that the pool closed at 6 PM because they were low on staff so by the time we got back from sightseeing, we weren’t able to get in the pool"
Cape Cod Holiday Estates, a VRI resort
Martha's Vineyard Getaway Cottage
Exterior
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/CozyBeachCottage-Please note rental details prior to booking. Thank You
Beach
Charming/CozyBeachCottage-Please note rental details prior to booking. Thank You
9.8 out of 10, Exceptional, (19)
"A beautiful, serene and cozy cottage, in a beautiful quiet location. Close walk or drive to the beaches. Close proximity to see sunrises and sunsets. Feels like home away from home. Thank you for making it such a comfortable place to stay and for making communication so easy. Grateful to have found this sweet gem! Looking forward to the next stay!"
Charming/CozyBeachCottage-Please note rental details prior to booking. Thank You
12 VINEYARD VIEW - FULLY RENOVATED
Exterior
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
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Just steps from path down to the beach. Can easily go back and forth for baby's naps and lunch
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
Cozy cottage w/ remodeled kitchen - less than a mile from Woods Hole Ferry
Cozy cottage w/ remodeled kitchen - less than a mile from Woods Hole Ferry
7.8 out of 10, Good, (26)
"Nice 1-bedroom with easily accessible loft within walking distance of Woods Hole village. Very clean with a nice kitchen and bath. Needs some attention to the yard and to the sump pump. I was also disappointed that the window air conditioners had not been installed yet."
The price is SAR 451
SAR 1,428 total
includes taxes & fees
21 Nov - 22 Nov
Cozy cottage w/ remodeled kitchen - less than a mile from Woods Hole Ferry
Cozy Massachusetts Escape w/ Patio, Near Beaches!
Fairhaven Vacation Rental | 2BR | 1BA | 500 Sq Ft | 3 Exterior Steps Required
Cozy Massachusetts Escape w/ Patio, Near Beaches!
10.0 out of 10, Exceptional, (1)
Cozy Massachusetts Escape w/ Patio, Near Beaches!
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Exterior
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
New Rental - 2 bedrooms, 1.5 baths, with magnificent views.
4 Race Point-Maushop Village
New Rental - 2 bedrooms, 1.5 baths, with magnificent views.
10.0 out of 10, Exceptional, (19)
"Everything was perfect. Super clean. Location was perfect. House had everything you need. The owner even made sure the weather was great. "
New Rental - 2 bedrooms, 1.5 baths, with magnificent views.
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Property grounds
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
10.0 out of 10, Exceptional, (16)
"Warm and inviting property. Everything was perfect, from the solar lights on the patio to the fireplace in the living area. We enjoyed a walk to dinner. Walked to Carboat for coffee in the morning. Fun visit to Martha’s Vineyard and a pleasant stay in this house !"
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
2bdrm Captains Cottage Steps to Beach and Downtown Edgartown with Pool!
Front view of Lighthouse Cottage
2bdrm Captains Cottage Steps to Beach and Downtown Edgartown with Pool!
9.8 out of 10, Exceptional, (7)
"Enjoyed the stay"
The price is SAR 1,803
SAR 2,708 total
includes taxes & fees
17 Nov - 18 Nov
2bdrm Captains Cottage Steps to Beach and Downtown Edgartown with Pool!
Chappy cottage with private beach
Dike Bridge
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
Cozy Beach Cottage
Exterior
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!
Brandt Beach (private to residents and guests only)
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!
Maushop Village Getaway with Ocean Views, Steps to Private Beach
Front of property
Maushop Village Getaway with Ocean Views, Steps to Private Beach
9.8 out of 10, Exceptional, (29)
"Very pleasant! "
Maushop Village Getaway with Ocean Views, Steps to Private Beach
Martha's Vineyard 1BR, Pets Ok, 10 Min walk to beach or Edgartowns shops!
Entrance to the cottage and its private fenced in yard. Rose of sharon in bloom
Martha's Vineyard 1BR, Pets Ok, 10 Min walk to beach or Edgartowns shops!
9.6 out of 10, Exceptional, (74)
"Really a five star place. Well outfitted and surprising private even though you are close to town. Highly recommended."
Martha's Vineyard 1BR, Pets Ok, 10 Min walk to beach or Edgartowns shops!
Martha's Vineyard 3BR, Pets Ok, 10 Min Walk to Beach or Shops!
Living room w/large sectional couch, kitchen pass thru & new 32 LCD TV.
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!
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Outdoor dining
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
10.0 out of 10, Exceptional, (45)
"Perfect little property for our weekend getaway. Recently renovated, very clean and comfortable. Great location for a home base for our island explorations. We would definitely return."
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Chappy Summer Cabin!
Terrace/patio
Chappy Summer Cabin!
8.2 out of 10, Very Good, (33)
"Great host , amazing property "
Chappy Summer Cabin!
Cozy Family Cottage Circuit Ave OB Walk to Everything
Dining
Cozy Family Cottage Circuit Ave OB Walk to Everything
2.0 star property
Cozy Family Cottage Circuit Ave OB Walk to Everything
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
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
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.
Outdoor dining
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
10.0 out of 10, Exceptional, (44)
"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 SAR 451 and SAR 1,803 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?
Expedia is here to help you track down cheap cottages in Chilmark. To find your dream stay in a matter of clicks, use the filter tool to refine your search by amenities, budget and star rating.