Photo by Wen C.

Find hotels in Chilmark, MA from AED 381

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check Chilmark hotel prices

Tonight
26 Dec - 27 Dec
Tomorrow night
27 Dec - 28 Dec
This weekend
27 Dec - 29 Dec
Next weekend
3 Jan - 5 Jan

Filter by

Guest rating
Guest rating
Star rating

Compare 2,098 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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

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

8.8 out of 10, Excellent, (9)
"We had such a lovely time staying at this house. It was absolutely immaculate inside and appointed with everything we could need and more. The house is light and airy inside, which helped when we had a few days of rain. The location is secluded in the woods (be careful, we did find ticks on us) but a short drive away from the beaches. We will definitely be back "
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Outdoor dining

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.

10.0 out of 10, Exceptional, (45)
"We were in town for a wedding in Chilmark and the property was exactly what we needed!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

8.6 out of 10, Excellent, (22)
"We didn't realize how beautiful and unique the architecture of this residence was before we arrived. It is a gorgeous place and we were please by the cleanliness and simplicity of it. "
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach

Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach

3.0 out of 10, (2)
"We were shocked when we arrived at this property. The word "rustic" should be added to its description. The front door to the property is a sliding glass does that does not from the outside. When we walked through the house upon arriving, we walked through spiderwebs on the inside of the house, the smell of mildew was overwhelming, most of the windows had been screwed closed with no way to open them, there were rodent traps in every room, the mini splits (AC units) worked extremely well, the...
Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach
Water-view home with large deck, balcony, enclosed sunroom & peaceful location

Water-view home with large deck, balcony, enclosed sunroom & peaceful location

10.0 out of 10, Exceptional, (5)
"Spent a wonderful week at Lobsterville Landing — a delightful home perfect for time with friends and family. Only a quick walk to the beach, not that we were in a hurry to leave this beautiful home."
Water-view home with large deck, balcony, enclosed sunroom & peaceful location
Modern beach house - Walking distance to Philbin Beach
Ocean View

Modern beach house - Walking distance to Philbin Beach

10.0 out of 10, Exceptional, (27)
"Beautiful spacious home near beach. Perfect setup for our family. Lovely kitchen and deck. You could hear the birds and the waves from the deck. A perfect spot to enjoy this beautiful part of the Vineyard."
Modern beach house - Walking distance to Philbin Beach
Cozy Sanctuary with Water Views
Room

Cozy Sanctuary with Water Views

Cozy Sanctuary with Water Views
Cozy efficiency apartment/heated pool
Pool

Cozy efficiency apartment/heated pool

9.8 out of 10, Exceptional, (17)
"What a wonderful gem in the woods of Chilmark. The pool is the icing on the cake. Ronnie was such a wonderful host! Hope to return in the fall, but definitely again in the future."
Cozy efficiency apartment/heated pool
Magical House in the Trees with Water View - Secluded Area
Windows EVERYWHERE!

Magical House in the Trees with Water View - Secluded Area

10.0 out of 10, Exceptional, (76)
"Lisa’s home truly is unique. Located in a very beautiful part of the island. It’s far from the ferry (and the crowds :)) so it would be best to stay here if you have a car on island. Ubering could be difficult and expensive. The privacy and fenced in back yard are unbeatable. Comfortable beds, well equipped kitchen, close to gay head and lobsterville beaches. We had such an amazing stay!!"
Magical House in the Trees with Water View - Secluded Area
Charming and comfortable custom home. Private ocean beach/pond access + kayaks
Welcome to our peaceful home in Aquinnah, just above Menemsha Pond!

Charming and comfortable custom home. Private ocean beach/pond access + kayaks

10.0 out of 10, Exceptional, (56)
"We had a wonderful stay in Aquinnah in September 2024! We loved the house, and its design and setting gave us a great base to explore the island. With access to six plus beaches and the use of kayaks, there’s lots to see if you want to, but also lots of great places just to sit and relax. The deck at the house is a wonderful place to watch sunrises, sunsets, and moon rises too! We will be back!"
Charming and comfortable custom home. Private ocean beach/pond access + kayaks
Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
Living area

Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.

10.0 out of 10, Exceptional, (21)
"My wife, 2 dogs and I visited for a week. This house was well appointed, clean and relaxing. The deck, yard and views are spectacular. We were looking for a quiet place to decompress and recharge and this house did the trick. Christian was very responsive and helpful to every question. I highly recommend."
Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
Beautiful Aquinnah Home: Ocean View, Walk to Beach
Terrace/patio

Beautiful Aquinnah Home: Ocean View, Walk to Beach

3.0 star property
Beautiful Aquinnah Home: Ocean View, Walk to Beach
Quaint & Quiet Quitsa: 3-bedroom house with WiFi, AC in peaceful Chilmark
Property grounds

Quaint & Quiet Quitsa: 3-bedroom house with WiFi, AC in peaceful Chilmark

2.0 star property
Quaint & Quiet Quitsa: 3-bedroom house with WiFi, AC in peaceful Chilmark
Fully Appointed Water View House Ten Minutes Walk from Beach
Gay Head from front deck

Fully Appointed Water View House Ten Minutes Walk from Beach

10.0 out of 10, Exceptional, (8)
"Loved the house and location. Host was very helpful. Hope to be back!"
Fully Appointed Water View House Ten Minutes Walk from Beach
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Property grounds

Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

9.8 out of 10, Exceptional, (37)
"We enjoyed our time here. The house sits is in a very quiet landscape. Remote and relaxing. Just what we have been looking for. Quick drive to beautiful beaches and the cliffs near Gays Lighthouse. Highly recommend this gem."
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Luxury Home in Exclusive Aquinnah
Exterior

Luxury Home in Exclusive Aquinnah

10.0 out of 10, Exceptional, (12)
"Great house and the host did a great job in answering all of our questions and being available when we needed them."
Luxury Home in Exclusive Aquinnah
Airey Two Bedroom Menemsha cottage
Menemsha cottage

Airey Two Bedroom Menemsha cottage

10.0 out of 10, Exceptional, (4)
"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!"
Airey Two Bedroom Menemsha cottage
Private Hillside Home with Open Property and a Fully Equipped Kitchen

Private Hillside Home with Open Property and a Fully Equipped Kitchen

9.6 out of 10, Exceptional, (8)
"The house was great"
Private Hillside Home with Open Property and a Fully Equipped Kitchen
Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W/D

Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W/D

7.8 out of 10, Good, (11)
"Nice and clean property; it’s really back “off the beaten path”."
Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W/D
Beautiful dog-friendly home with water view, balcony & washer/dryer

Beautiful dog-friendly home with water view, balcony & washer/dryer

7.8 out of 10, Good, (14)
"A Vacasa managed property that has everything you could want. We stayed 4 nights with our whole family and our small dog. It had everything we could want and we enjoyed ourselves. Recently redone, with good fit and finish and places to hang cook and relax off a dirt road that is well situated. Our only comments would be that there were some things needing fixing like the grill handle, lights not in sockets, and general disarray of bedding and supplies in the closets. While clean and fresh...
Beautiful dog-friendly home with water view, balcony & washer/dryer
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.
Don't see what you're looking for?
See all available properties in Chilmark
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Where is the best place for a stay in Chilmark?

Located 16.5 mi (26.6 km) from the heart of Chilmark, Holiday Inn Cape Cod-Falmouth, an IHG Hotel is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Sea Crest Beach Resort and Mansion House Inn And Spa. See all available top hotels, or vacation rentals in Chilmark.

What are some of the best vacation rentals in Chilmark?

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks: This highly rated vacation home rental in Chilmark is located near the beach and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. See all vacation rentals in Chilmark.

If I need to cancel my hotel reservation in Chilmark, will I receive a refund?

Yes! The majority of hotel room reservations are fully refundable as long as you cancel before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you have a reservation that's non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chilmark.

Where can I learn more about changing or cancelling my trip to Chilmark?

For more details about changing or cancelling your trip to Chilmark, go to https://www.expedia.com/service/.

What's the best place to stay near Aquinnah Cliffs?

The Little B&B in Aquinnah is one of the top choices for your stay based on our traveler data, and this B&B offers free breakfast and free parking. It's located 1.3 mi (2.1 km) from Aquinnah Cliffs.

What about the best place to stay near Gay Head Lighthouse?

One of the top choices for your stay is The Little B&B in Aquinnah, located 1.3 mi (2 km) from Gay Head Lighthouse, and this B&B offers free breakfast and free parking.

What are some hotels with pools in Chilmark?

Holiday Inn Cape Cod-Falmouth, an IHG Hotel: Offers a snack bar/deli, an indoor pool, and free self parking. Sea Crest Beach Resort and Mansion House Inn And Spa are two additional hotels with an onsite pool. View all hotels with pools in Chilmark.

What is the best hotel near Martha's Vineyard Airport (MVY)?

Mansion House Inn And Spa is one of the top choices for your stay and is a popular 3.5-star hotel featuring a full-service spa and free breakfast. It's located 4.5 mi (7.2 km) from Martha's Vineyard Airport. Another good option near the airport is HI Martha's Vineyard.

What is staying in Chilmark like?

Visitors can enjoy all that Chilmark has to offer including the beaches, wineries, and festivals. Tourists can also enjoy the city's local tours and university setting. In Chilmark, there are 79 hotels and other accommodations to choose from. Find out more about Chilmark.

What should I do while I'm visiting Chilmark?

Natural beauty is on display at Menemsha Beach, Lucy Vincent Beach, and Edys Island. A couple of additional sights to add to your agenda are Chilmark Town Hall and Chilmark Public Library. Check out what more to see and do in Expedia's Chilmark guide.

What's the weather like in Chilmark?

The hottest months are usually August and July with an average temp of 68°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Chilmark is 50 inches.