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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sep - 14 Sep
In two months
10 Oct - 12 Oct

Cottages in Chilmark

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

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
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
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, (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.
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, (68)
"Clean property, great location"
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Cozy Beach Cottage
Beach nearby, sun loungers, beach towels

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
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (5)
"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
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, (10)
"Charming village, cute cottage and walking distance to beach and shops."
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
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"
The price is SAR 4,500
SAR 5,744 total
includes taxes & fees
14 Aug - 15 Aug
WATERFRONT Downtown Cottage w/ Beach
Relaxing Island Retreat, Cozy Cottage, Lamberts Cove Beach Access!
Beach nearby, sun loungers, beach towels

Relaxing Island Retreat, Cozy Cottage, Lamberts Cove Beach Access!

9.6 out of 10, Exceptional, (20)
"Such a cute cottage and perfect for me and my Dad. We came to MV for a family wedding and the cottage was in the perfect location - central to all of the festivities. Also a very clean stay!"
Relaxing Island Retreat, Cozy Cottage, Lamberts Cove Beach Access!
Make Lasting Memories In This Adorable Vineyard Cottage!
Exterior

Make Lasting Memories In This Adorable Vineyard Cottage!

9.8 out of 10, Exceptional, (146)
"Absolutely loved this place. Had everything we needed. Such cute decor. Perfect cute little rental in convenient location. "
The price is SAR 938
SAR 1,916 total
includes taxes & fees
1 Sep - 2 Sep
Make Lasting Memories In This Adorable Vineyard Cottage!
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!
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
Beach nearby, sun loungers, beach umbrellas, beach towels

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

9.6 out of 10, Exceptional, (44)
"Nice rental property very close to ocean in a very quiet neighborhood. Would recommend"
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
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
Cozy New TimberFrame Vineyard Haven!
Exterior

Cozy New TimberFrame Vineyard Haven!

10.0 out of 10, Exceptional, (25)
"We very much enjoyed our few days in MV here. The place was perfect, clean and cozy. "
Cozy New TimberFrame Vineyard Haven!
Peaceful hideaway on Westport Point
Fridge, microwave, oven, stovetop

Peaceful hideaway on Westport Point

9.8 out of 10, Exceptional, (39)
"Beautiful yard, great location and comfortable cottage"
Peaceful hideaway on Westport Point
Cape Cod Cottage steps from Private Beach
TV

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 -
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 -
Maushop Village Getaway with Ocean Views, Steps to Private Beach
Dining

Maushop Village Getaway with Ocean Views, Steps to Private Beach

10.0 out of 10, Exceptional, (32)
"Lovely cottage just steps from the beach - if I'm in the area, would definitely go back again!"
Maushop Village Getaway with Ocean Views, Steps to Private Beach
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 SAR 1,220
SAR 1,954 total
includes taxes & fees
10 Sep - 11 Sep
Charming cottage overlooking the bay in Padanaram Village.
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

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

10/10 Excellent
"Unexpected gem. On the waterfront, bus line, and shopping area. "
Tamara 1-night trip
Posted 23 hours ago
Vineyard Harbor Motel - Private Beach

Frequently asked questions

How much do cottages in Chilmark cost?
You can expect to pay between SAR 938 and SAR 4,500 per night for cottages in Chilmark. No matter your budget, a fantastic stay is just a click or two away on Expedia. 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 that vacations should be a walk in the park, so if you're searching for cottages in Chilmark at an affordable price, Expedia can help. Keep the budget under control and pick a low-cost option far away from the city rush, or book a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Chilmark?
With Expedia's filter tool, sourcing cheap cottages in Chilmark is a snap. To find properties that'll make your wallet smile, narrow down your search by star rating, budget and amenities.