Chilmark

Travel Guide

A dock with boats, a small wooden structure, and a forested shoreline.
A beach with large rock formations and the ocean in the background.
A sunset over a calm sea with a rocky shoreline and a distant buoy.
A coastal landscape with a lighthouse, cliffs, and the ocean.
A building with a red door and a white fish sign.
Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool

Chilmark MA
The price is CA $530 per night from Sep 28 to Sep 29
CA $530
CA $812 total
Sep 28 - Sep 29
includes taxes & fees
Stay at this apartment in Chilmark. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Edys Island and Squibnocket Pond are located ...
9.6/10 Exceptional! (26 reviews)
"Beautiful property with an amazing pool. Great place to stay!"

Reviewed on Aug 30, 2026

Cozy efficiency apartment/heated pool
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd North Falmouth MA
The price is CA $231 per night from Oct 25 to Oct 26
CA $231
CA $345 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this beach hotel in North Falmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Sea Crest Beach Resort
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
The price is CA $188 per night from Oct 12 to Oct 13
CA $188
CA $215 total
Oct 12 - Oct 13
includes taxes & fees
Book a stay at this business-friendly hotel in Falmouth. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Woods Hole Ferry Terminal ...
Iris Hotel Cape Cod
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.
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

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

Chilmark MA
Book a stay at this family-friendly vacation home in Chilmark. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Waskosim's Rock ...
8.6/10 Excellent! (4 reviews)
"It’s a beautiful property that deserves some love. We had a wonderful weekend despite this tired little house. We rented the last weekend of the summer, 3 nights total for around 2000. It’s overpriced. Oven does not work properly. The tv is outdated (could not cast from your smart devices). The shower ..."

Reviewed on Sep 21, 2026

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool

Chilmark MA
Stay at this apartment in Chilmark. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Edys Island and Squibnocket Pond are located ...
9.6/10 Exceptional! (26 reviews)
"Beautiful property with an amazing pool. Great place to stay!"

Reviewed on Aug 30, 2026

Cozy efficiency apartment/heated pool
The Club at New Seabury

The Club at New Seabury

3.5 out of 5
95 Shore Drive West Mashpee MA
Book a stay at this beach aparthotel in Mashpee. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions South Cape Beach State Park and Popponesset ...
9/10 Wonderful! (370 reviews)
"The check in staff and staff at the 95 Restaurant were all excellent! The score is not perfect because the accomodations are dated and there was no ability to secure the unit because the locks required keys we did not have. If we didn't have familiarity with the area this would have been unnerving. ..."

Reviewed on Sep 25, 2026

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.

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