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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Cottages in Chilmark

Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.
On the beach, sun-loungers, beach towels

Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great 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!"
The price is AU$989
includes taxes & fees
17 Sept - 18 Sept
Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Dining

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

9.6 out of 10, Exceptional, (69)
"Clean property, great location"
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Terrace/patio

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

10.0 out of 10, Exceptional, (53)
"This home serves as a lovely base while vacationing on Martha’s Vineyard. It’s an easy walk to some great places to eat, a grocery store, boutiques, and more. Plus, it’s just down the street from the Vineyard Haven ferry terminal.The host is both incredibly proactive and responsive. Stocked with all the right stuff, immaculate, and decorated with cute coastal flair, this home makes for a super comfortable stay."
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
WATERFRONT Downtown Cottage w/ Beach
Interior

WATERFRONT Downtown Cottage w/ Beach

10.0 out of 10, Exceptional, (47)
"Super clean, great location and all the amenities a true gem right on the beach. Host was wonderful"
WATERFRONT Downtown Cottage w/ Beach
Make Lasting Memories In This Adorable Vineyard Cottage!
Exterior

Make Lasting Memories In This Adorable Vineyard Cottage!

9.8 out of 10, Exceptional, (147)
"Absolutely loved this place. Had everything we needed. Such cute decor. Perfect cute little rental in convenient location. "
The price is AU$802
includes taxes & fees
1 Sept - 2 Sept
Make Lasting Memories In This Adorable Vineyard Cottage!
Cozy family-friendly cottage on beautiful Shining Sea bike trail
Fridge, microwave, oven, stovetop

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
Small One Bedroom Private Cottage on Large Quiet Property.
TV

Small One Bedroom Private Cottage on Large Quiet Property.

9.8 out of 10, Exceptional, (7)
"Absolutely perfect, right down to the brands of soaps and shampoos! Beautiful artwork everywhere. I wouldn't change a thing!"
Small One Bedroom Private Cottage on Large Quiet Property.
Beautiful Carriage House on the Chop
Exterior

Beautiful Carriage House on the Chop

10.0 out of 10, Exceptional, (24)
"Loved staying at The Carriage House! Very beautiful place to relax and plan all the wonderful things you get to do on the island. Easy communication, very comfortable beds and well stocked kitchen."
Beautiful Carriage House on the Chop
Charming cottage overlooking the bay in Padanaram Village.
Marina

Charming cottage overlooking the bay in Padanaram Village.

2.0 star property
10.0 out of 10, Exceptional, (8)
"Super location, very nice accommodations, very clean, modern and comfortable "
The price is AU$767
includes taxes & fees
17 Sept - 18 Sept
Charming cottage overlooking the bay in Padanaram Village.
Cozy Beach Cottage
Beach nearby, sun-loungers, beach towels

Cozy Beach Cottage

9.8 out of 10, Exceptional, (50)
"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, Sleeps 4, outdoor shower
Beach nearby, sun-loungers, beach towels

Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, Sleeps 4, 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, Sleeps 4, outdoor shower
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
TV

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

2.0 star property
9.2 out of 10, Wonderful, (11)
"Charming village, cute cottage and walking distance to beach and shops."
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
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
Chappaquiddick, Cozy 2 Bedroom, October Dates Available!
Marina

Chappaquiddick, Cozy 2 Bedroom, October Dates Available!

10.0 out of 10, Exceptional, (26)
"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, October Dates Available!
Edgartown cottage in a garden setting. New and near bike path in Katama
Property grounds

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

10.0 out of 10, Exceptional, (5)
Edgartown cottage in a garden setting. New and near bike path in Katama
Cape Cod Cottage steps from Private Beach
TV

Cape Cod Cottage steps from Private Beach

10.0 out of 10, Exceptional, (36)
"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 -
Beach nearby, sun-loungers, beach umbrellas, beach towels

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 -
A Charming Vineyard Cottage Just Off the Pond
3 bedrooms, free WiFi, bed sheets

A Charming Vineyard Cottage Just Off the Pond

9.4 out of 10, Exceptional, (39)
"This is a really great house, in a really great location, with a really great owner! We had a great week in this house and wouldn’t hesitate to book again!"
A Charming Vineyard Cottage Just Off the Pond
Bright and cozy menemsha cottage
Fridge, microwave, oven, stovetop

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
Popponesset-3 Bed, 1 bath, Sleeps 6, outdoor shower. Walk to Bluff Ave beach
Beach nearby, sun-loungers, beach towels

Popponesset-3 Bed, 1 bath, Sleeps 6, outdoor shower. Walk to Bluff Ave beach

9.8 out of 10, Exceptional, (15)
"Nice place. Very clean and close to the beach. Great place for a cape week"
Popponesset-3 Bed, 1 bath, Sleeps 6, outdoor shower. Walk to Bluff Ave 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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Top Chilmark Hotel Reviews

Sea Crest Beach Resort

Sea Crest Beach Resort

10/10 Excellent
"Beautiful place to stay "
Stephanie 2-night trip
Posted 20 hours ago
Sea Crest Beach Resort

Frequently asked questions

How much do cottages in Chilmark cost?
Cottages in Chilmark range between AU$767 and AU$989 per night. These properties offer a chance to get in touch with nature — at a price you can afford. This price was 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.
What is there to do in Chilmark near my cottage?
You'll find loads of fantastic things to do in Chilmark. Head for attractions like Lamberts Cove Beach, Menemsha Beach and Lucy Vincent Beach. Long Point Beach, The Yard and Gay Head Lighthouse also lure many visitors.