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Search Cottages in Chilmark

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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 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 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!
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
Cape Cod Cottage steps from Private Beach
Exterior

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
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
WATERFRONT Downtown Cottage w/ Beach
Main level back deck with view of the Vineyard Haven harbor

WATERFRONT Downtown Cottage w/ Beach

10.0 out of 10, Exceptional, (41)
"First time on the Vinyard. Home is wonderful and restful and appointed very nicely. Host was great to work with and everything about the place made us want to come back. Beautiful views and very relaxing. "
WATERFRONT Downtown Cottage w/ Beach
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.
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!
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
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
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community

Charming Seaside Cottage Central to the Beach and New Seabury Resort Community

2.0 star property
10.0 out of 10, Exceptional, (3)
"Perfect cottage"
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
★The Islander | Steps From Water, Fire Pit, AC★
Living area

★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!
Timber Front

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!
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)
"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

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
Exterior

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
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 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.
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