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Oct 3 - Oct 5
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Oct 10 - Oct 12
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Oct 24 - Oct 26
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Nov 21 - Nov 23

Cottages in Chilmark

Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.
Exterior

Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.

10.0 out of 10, Exceptional, (30)
"Cute and efficient lodging stocked with everything you would ever need. We enjoyed our brief stay as home base to exploring the Cape."
Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.
Beautiful Carriage House on the Chop
Exterior

Beautiful Carriage House on the Chop

10.0 out of 10, Exceptional, (24)
"Great location, well outfitted, great kitchen, comfortable beds. Would stay again."
Beautiful Carriage House on the Chop
Cozy Beach Cottage
Exterior

Cozy Beach Cottage

10.0 out of 10, Exceptional, (53)
"This was the perfect property for our visit to Martha’s Vineyard. The owners were so responsive and gave us a seamless experience. I would definitely stay at the Cozy Cottage again! "
Cozy Beach Cottage
Contemporary cottage with outdoor shower infrared sauna 6 Min drive to the beach
Terrace/patio

Contemporary cottage with outdoor shower infrared sauna 6 Min drive to the beach

9.0 out of 10, Wonderful, (2)
"Great house with enjoyable blend of spaciousness and cozy appeal. Kitchen was well appointed and great overall aesthetic, layout - roomy for 5. Upstairs suite very open and lots of windows in house. 5 min drive to BREATHTAKING reservation on beach ($20 to park for non members and well worth it), peaceful Japanese gardens nearby too. There's a super cute 500ft ferry ride ($35 round trip) to get to and from this location so plan for food accordingly!"
Contemporary cottage with outdoor shower infrared sauna 6 Min drive to the beach
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
Property grounds

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

2.0 star property
8.8 out of 10, Excellent, (14)
"Charming village, cute cottage and walking distance to beach and shops."
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
Make Lasting Memories In This Adorable Vineyard Cottage!
Property grounds

Make Lasting Memories In This Adorable Vineyard Cottage!

9.8 out of 10, Exceptional, (150)
"Absolutely loved this place. Had everything we needed. Such cute decor. Perfect cute little rental in convenient location. "
$429 nightly
The price is $479
Oct 1 - Oct 2
Total with taxes and fees
Make Lasting Memories In This Adorable Vineyard Cottage!
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Exterior

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

10.0 out of 10, Exceptional, (54)
"We had a wonderful stay! The place was clean, cute, and very conveniently located. Would definitely return!"
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Charming cottage overlooking the bay in Padanaram Village.
Terrace/patio

Charming cottage overlooking the bay in Padanaram Village.

2.0 star property
10.0 out of 10, Exceptional, (8)
"Beautiful property. The cottage is beautifully decorated and well maintained. Amazing location. Host was very good at communicating. "
$406 nightly
The price is $454
Oct 16 - Oct 17
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Exterior

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

10.0 out of 10, Exceptional, (28)
"Perfect for my family of 4. Very walkable to everything Vineyard Haven. "
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach
Exterior

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

5.8 out of 10, (28)
"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
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Property grounds

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

8.6 out of 10, Excellent, (85)
"Loved the neighborhood and proximity to the beach and marketplace. Cute space, host was very responsive. Would stay again"
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Oceanside Cottage with Private Beach Access
Terrace/patio

Oceanside Cottage with Private Beach Access

9.8 out of 10, Exceptional, (7)
"Excellent sea view and very quiet place"
Oceanside Cottage with Private Beach Access
Spacious Home - 1500 ft from Beach & Circuit Ave
Exterior

Spacious Home - 1500 ft from Beach & Circuit Ave

10.0 out of 10, Exceptional, (12)
"Great stay, clean, great location and Judy the owner was always available if anything came up!"
Spacious Home - 1500 ft from Beach & Circuit Ave
★The Islander | Steps From Water, Fire Pit, AC★
Property grounds

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

10.0 out of 10, Exceptional, (51)
"We stayed for a sisters weekend and it was just perfect!"
★The Islander | Steps From Water, Fire Pit, AC★
Small One Bedroom Private Cottage on Large Quiet Property.
Exterior

Small One Bedroom Private Cottage on Large Quiet Property.

9.8 out of 10, Exceptional, (9)
"Absolutely perfect, right down to the brands of soaps and shampoos! Beautiful artwork everywhere. I wouldn't change a thing!"
$332 nightly
The price is $371
Oct 12 - Oct 13
Total with taxes and fees
Small One Bedroom Private Cottage on Large Quiet Property.
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, (71)
"Clean property, great location"
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Cape Cod Cottage steps from Private Beach
Exterior

Cape Cod Cottage steps from Private Beach

10.0 out of 10, Exceptional, (39)
"Excellent location- we will be back! "
Cape Cod Cottage steps from Private Beach
This Romantic Cottage is Simply a Cut Above -
Exterior

This Romantic Cottage is Simply a Cut Above -

10.0 out of 10, Exceptional, (58)
"What a great Cottage. We would stay there again."
This Romantic Cottage is Simply a Cut Above -
Bright and cozy menemsha cottage
Property grounds

Bright and cozy menemsha cottage

10.0 out of 10, Exceptional, (5)
"Peaceful location near conservation trail and a short drive to Lucy Vincent and the Chilmark Store. Clean, spacious and comfortable for our family of six adults. The owner mailed the key and information about the house ahead of our stay, which was helpful. Highly recommended!"
Bright and cozy menemsha cottage
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
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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Top Chilmark Hotel Reviews

Falmouth Tides

Falmouth Tides

10/10 Excellent
"A great little find, modern and stylish but most importantly right on the beach and in easy walking distance to the Island Queen ferry to Marthas Vinyard. The coffee truck outside also is a really nice touch."
Tim 2-night trip
Posted 23 hours ago
Falmouth Tides

Find out more about Chilmark

Find out more about Chilmark

Chilmark Cottages information

Number of reviews
629
Accommodation
160 Cottages
Lowest Price
$371
Highest Price
$479

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