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Find hotels in Chilmark, MA from CA $143

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Top 10 Chilmark hotels and places to stay

Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
8.0 out of 10, Very good, (3)
Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
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
Cozy efficiency apartment/heated pool
10.0 out of 10, Exceptional, (16)
"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
Cozy Sanctuary with Water Views
Cozy Sanctuary with Water Views
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
8.4 out of 10, Very good, (21)
"Wonderful place for a getaway to MV. Well appointed, comfy home with great pool. Plenty of privacy but easy to get to. Enjoyed our stay"
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Beautiful dog-friendly home with water view, balcony & washer/dryer
8.0 out of 10, Very good, (11)
"The house is tucked down a magical driveway with serene surroundings. Unfortunately, there were a few things that left us feeling a bit disappointed. It was clear we were one of the first visitors of the season. The house was quite musty, the washer was filled with water and mold, the showers were not cleaned, showing clear hard water, spider webs, and some build up. The comforter in the master was stained, including some blood. The AC on the top floor was not working. Lastly, the door handle...
Beautiful dog-friendly home with water view, balcony & washer/dryer
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
8.4 out of 10, Very good, (6)
"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
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
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
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
10.0 out of 10, Exceptional, (41)
"Beautiful and peaceful "
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
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
Private Hillside Home with Open Property and a Fully Equipped Kitchen
9.6 out of 10, Exceptional, (7)
"SUV a must.Quiet and remote location. Home is spacious but needs small repairs in upstairs bathrooms. Also, changing the water filter more frequently may lower the sense of iron from the water. Kitchen was equipped with all needed for a one week stay. Perfect place to reflect surrounded by beautiful hiking trails and close proximity to the beach - not for swimming but gazing at the ocean and hiking over beach stones."
Private Hillside Home with Open Property and a Fully Equipped Kitchen
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
Magical House in the Trees - 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 - Secluded Area
Beautiful Aquinnah Home: Ocean View, Walk to Beach
3.0 star property
Beautiful Aquinnah Home: Ocean View, Walk to Beach
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
10.0 out of 10, Exceptional, (33)
"Fantastic beach cabin in a nice location, close to Gay Head lighthouse and several beaches, including the dog-friendly Lobsterville. Good views, plenty of land, we had a good time!"
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
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.
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
Peaceful Chilmark Farmhouse by Menemsha Beach
3.0 star property
Peaceful Chilmark Farmhouse by Menemsha Beach
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
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Frequently asked questions

Where is the best place for a stay in Chilmark?

Based on Expedia's traveler preferences, Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks is a top place to stay in Chilmark. Other good options for your trip to the area are Sea Crest Beach Hotel and Summercamp. 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 hotel for a family vacation in Chilmark?

Menemsha Inn & Cottages is a top 3-star hotel on Expedia for families, and features 2 restaurants and free parking. Attractions in the area like Island Cove Adventures are also fun for the whole family. Find more child-friendly accommodations in Chilmark.

What's the best pet-friendly hotel in Chilmark?

Menemsha Inn & Cottages is a top hotel for people traveling with their pets, and offers 2 restaurants and a 24-hour fitness center for its human guests. See more pet-friendly hotel accommodations in Chilmark.

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's the best accommodation to stay near the beach in Chilmark?

Menemsha Inn & Cottages is a top beach hotel offering 2 restaurants and free WiFi, located within a short 15-minute walk of Menemsha Beach. See more stays near the beach in Chilmark.

What are some hotels with pools in Chilmark?

Sea Crest Beach Hotel: Hotel, 2-minute walk from Cape Cod Beaches. Offers a children's pool, a seasonal outdoor pool, and a private beach. Holiday Inn Cape Cod-Falmouth, an IHG Hotel 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 spa hotel in Chilmark?

Menemsha Inn & Cottages is a highly recommended beach spa hotel featuring a 24-hour fitness center and outdoor tennis courts. See all spa hotels 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 81 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 Lucy Vincent Beach, Menemsha Beach, and Squibnocket Pond. A couple of additional sights to add to your agenda are Chilmark Chocolates and Menemsha Blues Charters. 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.