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Check prices for these dates

Next weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Chilmark Cottages

Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
Stroll through a charming neighborhood lined with classic homes and lush greenery.

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

2.0 star property
9.2 out of 10, Wonderful, (7)
"Perfect cottage"
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach
Situated in a residential area, this two-story house features a gabled roof and a beautiful garden with mature trees and shrubs.

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

5.6 out of 10, (24)
"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
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Welcome to this charming home with a front door, garage, and cozy porch area.

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

9.6 out of 10, Exceptional, (68)
"Clean property, great location"
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Cozy family-friendly cottage on beautiful Shining Sea bike trail
Enjoy cooking in this well-lit kitchen with a central island, sink, microwave, and coffee maker.

Cozy family-friendly cottage on beautiful Shining Sea bike trail

10.0 out of 10, Exceptional, (4)
"This cottage is charming and inviting. The hosts have outdone themselves with their attention to detail. This place has everything you could want or need. We hope to return someday! "
Cozy family-friendly cottage on beautiful Shining Sea bike trail
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Stunning two-story house with a central entrance, flanked by windows and a charming porch.

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

10.0 out of 10, Exceptional, (53)
"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!
5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.
Stunning coastal homes line a scenic road leading to the sea.

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

10.0 out of 10, Exceptional, (28)
"We had a great trip and look forward to staying there again. Location is the best part!"
5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Set amidst a serene garden, this charming two-story house offers a peaceful retreat.

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

10.0 out of 10, Exceptional, (25)
"This was the perfect place for a weekend on the island. Great location and my son loved the upstairs rooms to play in. "
The price is CA $1,100
CA $1,405 total
includes taxes & fees
Aug 19 - Aug 20
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Cozy Beach Cottage
Charming single-story home with a gabled roof and covered porch, set amidst a well-manicured lawn and a large tree.

Cozy Beach Cottage

10.0 out of 10, Exceptional, (48)
"The property was prepared, very thoughtful and had everything you could think of for a wonderful beach Island stay. The only downside was cable because I’m addicted to TV and I would’ve appreciated at least a smart TV that I could connect my own Netflix. "
Cozy Beach Cottage
Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower
Relax in a serene outdoor space surrounded by lush greenery, complete with a deck and storage shed.

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

9.8 out of 10, Exceptional, (27)
"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
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach
Situated in a grassy yard, this charming house features a gabled roof and a welcoming front porch.

Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach

9.6 out of 10, Exceptional, (4)
"The Pinkletink was a quaint home for a wonderful visit to Martha's Vinyard. It is in a quiet neighborhood and a nice walk from both the beach and the town of Oak Bluffs. Perfect location for a couple wanting to visit Martha's Vinyard and enjoy the island."
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach
4 Mi to Bristol Beach: Cottage w/ Pond & Deck
Relax and dine al fresco on this serene outdoor deck, featuring a grill station and comfortable seating.

4 Mi to Bristol Beach: Cottage w/ Pond & Deck

2.0 star property
4 Mi to Bristol Beach: Cottage w/ Pond & Deck
Make Lasting Memories In This Adorable Vineyard Cottage!
Relax on the deck surrounded by lush greenery and enjoy the serene atmosphere.

Make Lasting Memories In This Adorable Vineyard Cottage!

9.8 out of 10, Exceptional, (145)
"Absolutely loved this place. Had everything we needed. Such cute decor. Perfect cute little rental in convenient location. "
Make Lasting Memories In This Adorable Vineyard Cottage!
Oceanside Cottage with Private Beach Access
Guests can enjoy ocean views from the deck leading to this residential building.

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
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
Walk along the beach, where the shore meets the calm waters and a peaceful atmosphere awaits.

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

9.6 out of 10, Exceptional, (43)
"Nice rental property very close to ocean in a very quiet neighborhood. Would recommend"
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
12 VINEYARD VIEW - FULLY RENOVATED
Relax under the covered patio with a beautiful garden view.

12 VINEYARD VIEW - FULLY RENOVATED

9.8 out of 10, Exceptional, (43)
"Definitely would stay again!"
12 VINEYARD VIEW - FULLY RENOVATED
Cozy New TimberFrame Vineyard Haven!
Situated in a lush landscape, this cabin features a welcoming front porch with a bench and a small enclosed area perfect for relaxation or dining.

Cozy New TimberFrame Vineyard Haven!

10.0 out of 10, Exceptional, (24)
"We very much enjoyed our few days in MV here. The place was perfect, clean and cozy. "
Cozy New TimberFrame Vineyard Haven!
Cozy vineyard cottage close to downtown with outdoor living space and amentiies.
Relax in an outdoor space with a hot tub and patio.

Cozy vineyard cottage close to downtown with outdoor living space and amentiies.

8.0 out of 10, Very good, (1)
"The property manager was wonderful to work with. The property location was perfect. The property was fairly clean but did have a musty smell. Would suggest the use of a dehumidifier. Overall, our stay here was great and enjoyable. We would definitely stay here again."
Cozy vineyard cottage close to downtown with outdoor living space and amentiies.
Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!
Exterior

Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!

The price is CA $551
CA $1,078 total
includes taxes & fees
Sep 1 - Sep 2
Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!
Cape Cod Cottage steps from Private Beach
Set amidst a charming white picket fence, this two-story house features a covered porch and a stone wall.

Cape Cod Cottage steps from Private Beach

10.0 out of 10, Exceptional, (35)
"Lovely cottage in great location to poppaneset and the beach."
Cape Cod Cottage steps from Private Beach
This Romantic Cottage is Simply a Cut Above -
Set amidst a well-maintained lawn, this home features a single-story design with a gabled roof and a two-car garage.

This Romantic Cottage is Simply a Cut Above -

10.0 out of 10, Exceptional, (58)
"Such a beautiful cottage for a Martha’s Vineyard stay. The home is very clean and nicely designed and furnished; kitchen is well equipped for cooking and grilling; location is great, about 2 miles from the beach and close to Edgartown. The owner kept in touch and we appreciated how responsive she was to any question we had about the island. We visited in late April, and although that is not technically “high season,” it was a lovely time to visit. We had great weather; many shops and restaurants...
This Romantic Cottage is Simply a Cut Above -
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
"I love that I can walk out of my room and be right on the beach. "
Erin 2-night trip
Posted 21 hours ago
Falmouth Tides