Photo by Wen C.

Search Chilmark Cottage Rentals from CA $552

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select Chilmark Cottages

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Beach nearby, sun loungers, beach towels

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

9.6 out of 10, Exceptional, (64)
"Clean property, great location"
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.
On the beach, sun loungers, beach towels

5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.

10.0 out of 10, Exceptional, (20)
"Maushop is the perfect place for a family getaway right on the ocean. The property was clean and spacious for a tiny cottage. We had a wonderful time."
The price is CA $552
CA $1,222 total
includes taxes & fees
May 21 - May 22
5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach
Property grounds

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

6.2 out of 10, (17)
"Great location and private beach access. Charming enclave perfect for our weekend getaway."
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach
Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower
Beach nearby, sun loungers, beach towels

Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower

10.0 out of 10, Exceptional, (23)
"This is our 2nd time at this property and we loved it again. The location is great. The property was super clean and inviting. Everything we needed to enjoy our stay. Just excellent across the board."
Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower
Oceanside Cottage with Private Beach
Terrace/patio

Oceanside Cottage with Private Beach

10.0 out of 10, Exceptional, (3)
"Excellent sea view and very quiet place"
Oceanside Cottage with Private Beach
2-bdrm Cottage | Close to Everything | Pet Friendly
Exterior

2-bdrm Cottage | Close to Everything | Pet Friendly

9.8 out of 10, Exceptional, (9)
"Many things to do nearby, beautiful town. The cottage was cozy, the beds comfortable. The views were great."
2-bdrm Cottage | Close to Everything | Pet Friendly
★The Islander | Steps From Water, Fire Pit, AC★
Terrace/patio

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

10.0 out of 10, Exceptional, (47)
"Our host, Matt was attentive and responsive. The house and neighborhood were exactly what we were looking for our brief getaway. It was off the beaten path, quiet and beautiful. Whatever we needed, we found within a short distance. "
★The Islander | Steps From Water, Fire Pit, AC★
Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability

Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability

10.0 out of 10, Exceptional, (25)
"My dad and I booked this cottage for a weekend trip. Easy to find, host was friendly and very responsive to our questions. Would definitely stay again!"
Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability
12 VINEYARD VIEW - FULLY RENOVATED
Property grounds

12 VINEYARD VIEW - FULLY RENOVATED

9.6 out of 10, Exceptional, (40)
"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
Peaceful hideaway on Westport Point
Beach

Peaceful hideaway on Westport Point

9.8 out of 10, Exceptional, (39)
"We love coming here. This year, we brought our croquet set and played in the big yard. Ate a lot of meals outside, as well, under the shade."
Peaceful hideaway on Westport Point
Cozy New TimberFrame Vineyard Haven!
Exterior

Cozy New TimberFrame Vineyard Haven!

10.0 out of 10, Exceptional, (19)
"We very much enjoyed our few days in MV here. The place was perfect, clean and cozy. "
Cozy New TimberFrame Vineyard Haven!
One Bedroom Private Cottage on Large Quiet Property.
TV

One Bedroom Private Cottage on Large Quiet Property.

9.8 out of 10, Exceptional, (6)
"Served as a great home-base while we explored the island!"
One Bedroom Private Cottage on Large Quiet Property.
Maushop Village Getaway with Ocean Views, Steps to Private Beach
Exterior

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
Cozy Beach Cottage
Beach nearby, sun loungers, beach towels

Cozy Beach Cottage

10.0 out of 10, Exceptional, (41)
"Really adorable place that is very well appointed for everything you need"
Cozy Beach Cottage
Martha's Vineyard 3BR, Pets Ok, 10 Min Walk to Beach or Shops!

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

9.6 out of 10, Exceptional, (68)
"We loved everything about this place and had a great week! Great proximity to Edgartown and the beach!"
The price is CA $553
CA $1,148 total
includes taxes & fees
May 28 - May 29
Martha's Vineyard 3BR, Pets Ok, 10 Min Walk to Beach or Shops!
Edgartown cottage in a garden setting. New and near bike path in Katama
Exterior

Edgartown cottage in a garden setting. New and near bike path in Katama

Edgartown cottage in a garden setting. New and near bike path in Katama
Popponesset-3 Bed, 1 bath, outdoor shower. Ten house walk to Bluff Ave beach
Beach nearby, sun loungers, beach towels

Popponesset-3 Bed, 1 bath, outdoor shower. Ten house walk to Bluff Ave beach

9.8 out of 10, Exceptional, (14)
"Nice place. Very clean and close to the beach. Great place for a cape week"
Popponesset-3 Bed, 1 bath, outdoor shower. Ten house walk to Bluff Ave beach
Cozy Family Cottage Circuit Ave OB Walk to Everything
Terrace/patio

Cozy Family Cottage Circuit Ave OB Walk to Everything

2.0 star property
Cozy Family Cottage Circuit Ave OB Walk to Everything
Chappy Summer Cabin!
Interior

Chappy Summer Cabin!

8.2 out of 10, Very good, (33)
"Great host , amazing property "
Chappy Summer Cabin!
Make Lasting Memories In This Adorable Vineyard Cottage!
Exterior

Make Lasting Memories In This Adorable Vineyard Cottage!

9.8 out of 10, Exceptional, (142)
"Easy to find, clean, easy check in and put. Super cute cottage. "
Make Lasting Memories In This Adorable Vineyard Cottage!
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

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
2 bedrooms, iron/ironing board, internet, bed sheets

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

8.8 out of 10, Excellent, (9)
"Private with beach access minutes away."
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
InnSeason Resorts Captain's Quarters
On the beach, white sand

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (168)
"Very peaceful "
InnSeason Resorts Captain's Quarters
The Club at New Seabury
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (315)
"Perfect little cottage!"
The price is CA $261
CA $299 total
includes taxes & fees
May 1 - May 2
The Club at New Seabury
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.