Chilmark, MA

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
$480 nightly
The price is $536 total per night from Sep 28 to Sep 29
$536 total
Sep 28 - Sep 29
Total with taxes and 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
Fully refundable
$218 nightly
The price is $249 total per night from Oct 21 to Oct 22
$249 total
Oct 21 - Oct 22
Total with taxes and 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 ...
7.6/10 Good! (507 reviews)
"Small rooms, okay bed. We got extra rolling bed but it was useless due to very poor mattress, even kids can’t sleep on them. They gave us 4 cards for 4 pool towels saying guests are stealing towels. If you loose towel card, you will be charged extra $15 per card. Overly priced food. Their payment ..."

Reviewed on Sep 20, 2026

Sea Crest Beach Resort
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
$133 nightly
The price is $152 total per night from Oct 12 to Oct 13
$152 total
Oct 12 - Oct 13
Total with taxes and 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 ...
8.4/10 Very Good! (394 reviews)
"Awesome!"

Reviewed on Sep 20, 2026

Iris Hotel Cape Cod
See all 2,238 properties in Chilmark
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.
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! (368 reviews)
"A"

Reviewed on Sep 10, 2026

The Club at New Seabury
Sea Mist Resort

Sea Mist Resort

3 out of 5
141 Great Neck Rd South Mashpee MA
Book a stay at this business-friendly aparthotel in Mashpee. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Regal Mashpee Commons and ...
8.6/10 Excellent! (169 reviews)
"Our Unit was very nice & clean. And the staff were quite pleasant. However, the mini blinds in the kitchen need replacing and a couple of cob webs removed. The pipes in the bathroom to the toilets are all rusted. And the green stains in the tub and sinks are not appealing. I take there is a lot if ..."

Reviewed on Sep 18, 2026

Sea Mist Resort
See all properties in Chilmark
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.

Stay near popular Chilmark attractions

Menemsha Beach

Why not spend a carefree afternoon at Menemsha Beach during your travels in Chilmark? Take in the festivals and sunsets in the area.
See properties

Things to do

Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
Beautiful Aquinnah Cliffs

Martha's Vineyard Private 4 hour Tour for groups up to 6 people

$700
per traveler
Martha's Vineyard Private 4 hour Tour for groups up to 6 people
Marthas Vineyard Luxury Tour

Marthas Vineyard Luxury Tour (2hrs)

$550
per traveler
Marthas Vineyard Luxury Tour (2hrs)
See all activities in Chilmark

Frequently asked questions

Is Chilmark worth visiting?
Chilmark is worth visiting for its serene coastal beauty, highlighted by Menemsha Beach and Lucy Vincent Beach. Travelers can relax on these scenic shores and also find local grocers for convenient self-catering during their visit.
When is the best time to visit Chilmark?
The best time to visit Chilmark is from June through August, when the destination is most popular. For travelers seeking fewer crowds and better value, the quieter months of October through December are a good bet, offering a more relaxed experience.
What is Chilmark known for?
Chilmark is known for its scenic coastal beauty, home to popular spots like Menemsha Beach and Lucy Vincent Beach. Travelers can also enjoy contemporary dance and performance at The Yard, an acclaimed cultural institution.
What is a good itinerary length for Chilmark?
A good itinerary length for Chilmark is two to three days to enjoy Menemsha Beach and Lucy Vincent Beach, plus a Martha's Vineyard tour. For a more relaxed trip, four to five days allows travelers to explore The Yard, spend more time at the beaches, and savor local seafood. See Chilmark Activities.
What are the top things to do in and around Chilmark?
Chilmark and its surrounding area offer beautiful beaches, natural reserves, and unique island tours:

  • Relax at Menemsha Beach, a scenic natural area.
  • Take a Shared Jaws tour to explore filming locations around Martha's Vineyard.
  • Stroll along Lucy Vincent Beach, another beautiful natural beach.
  • Visit The Yard, a local landmark.
  • Explore Waskosim's Rock Reservation, a tranquil nature spot.

How do I plan a trip to Chilmark?
To plan your trip to Chilmark, book flights, hotels, and rental cars in advance. Explore attractions like Menemsha Beach and Lucy Vincent Beach, and consider activities such as a Martha's Vineyard Private Tour or a Full-Island Tour. Always have indoor backup plans for outdoor activities to ensure weather flexibility.
Can I book a refundable hotel in Chilmark?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Chilmark by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Chilmark with Expedia?
Expedia makes it easier to plan your Chilmark trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Chilmark?
The best choice depends on your travel style. Hotels in Chilmark can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Chilmark trip on Expedia?
Once you've booked your Chilmark trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Chilmark trip?
Expedia offers customer support before, during, and after your Chilmark trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Chilmark?
If it's your first trip to Chilmark, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Chilmark hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Chilmark hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Chilmark

An aerial view of a coastal area with a sandy beach, a small island with buildings, and numerous boats in the water.

Vineyard Haven

A marina with numerous sailboats docked at the pier.

West Tisbury

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