Title: 5 Stars Hotels in Chilmark, Massachusetts from CA $335 - Find Cheap Chilmark Hotels With 5 Stars | Expedia.ca [Chilmark Travel Guide](https://expedia.ca/Chilmark.dx6135676)[Hotels in Chilmark](https://expedia.ca/Chilmark-Hotels.d6135676.Travel-Guide-Hotels)[Vacation Rentals in Chilmark](https://expedia.ca/Chilmark-Vacation-Rentals.d6135676.Travel-Guide-VacationRentals)[Flights to Chilmark](https://expedia.ca/Cheap-Flights-To-Chilmark.d6135676.Travel-Guide-Flights)[Things to do in Chilmark](https://expedia.ca/Things-To-Do-In-Chilmark.d6135676.Travel-Guide-Activities)[Chilmark Car Rentals](https://expedia.ca/Car-Rentals-In-Chilmark.d6135676.Car-Rental-Guide)[Chilmark Vacation Packages](https://expedia.ca/Chilmark.d6135676.Destination-Travel-Guides) ![In the fishing village of Menemsha in Marthas Vineyard. Delicious lobster rolls, clam chowder, lobster bisque etc. they'll boil your fresh lobster for you if you don't want to do it yourself. Some benches outside if you want to 'eat in' but best bet is to take your food down to the beach for a picnic. ](https://images.trvl-media.com/place/6135676/25271101-6fdf-4e1c-9afc-551d4a7f6b53.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Shobha George # 5 Stars Hotels in Chilmark, Massachusetts from CA $335 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chilmark 5 Star Hotels Tonight [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-12-21&endDate=2025-12-22&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-12-22&endDate=2025-12-23&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-12-26&endDate=2025-12-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chilmark 5-star hotels ![View from room](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/7b9d68f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/8ca88d65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/3c648f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/b242e02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbor View Hotel [](https://www.expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) Edgartown 8.8/10 Excellent (1000) "The area was safe and the dining experience was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Albert [](https://www.expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Chilmark-Hotels.s50-0-d6135676.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Chilmark-Hotels.s50-0-d6135676.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Chilmark. ![AutoCamp Cape Cod](https://images.trvl-media.com/lodging/50000000/49180000/49175900/49175859/3458b4d1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### AutoCamp Cape Cod 836 Palmer Avenue Falmouth MA CA $245 CA $335 total Dec 29 - Dec 30 includes taxes & fees 9.2/10 Wonderful! (301 reviews) [](https://expedia.ca/Falmouth-Hotels-AutoCamp-Cape-Cod.h49175859.Hotel-Information) ![Vineyard Square Hotel & Suites](https://images.trvl-media.com/lodging/1000000/700000/694900/694842/2026bafa_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Vineyard Square Hotel & Suites 38 North Water Street Edgartown MA [Get rates](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=694842&PinnedHotelID=694842&HadPinnedHotel=true®ionId=6135676) 9.2/10 Wonderful! (310 reviews) [](https://expedia.ca/Edgartown-Hotels-Vineyard-Square-Hotel-Suites.h694842.Hotel-Information) ![ We are back! Exceptional home 3min to bike path,beach,restaurants. Private pool](https://images.trvl-media.com/lodging/38000000/37010000/37009900/37009839/5ba03a06_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### We are back! Exceptional home 3min to bike path,beach,restaurants. Private pool North Falmouth MA [Get rates](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=37009839&PinnedHotelID=37009839&HadPinnedHotel=true®ionId=6135676) 9.8/10 Exceptional! (9 reviews) [](https://expedia.ca/North-Falmouth-Hotels-We-Are-Back-Exceptional-Home-3min-To-Bike-Path.h37009839.Hotel-Information) Still don't see what you're looking for? [See all properties in Chilmark.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=6135676&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=6135676&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=6135676&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=6135676&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=6135676&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=6135676&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Chilmark Menemsha Beach offers spectacular sunsets where locals and visitors gather with picnic dinners to watch the sky change colours. Hike the scenic trails at Waskosim's Rock Reservation or visit nearby Martha's Vineyard for charming shops and restaurants. [See all hotels in Chilmark](https://www.expedia.ca/Hotel-Search?startDate=2026-01-04&endDate=2026-01-05&adults=2®ionId=6135676) ![In the fishing village of Menemsha in Marthas Vineyard. Delicious lobster rolls, clam chowder, lobster bisque etc. they'll boil your fresh lobster for you if you don't want to do it yourself. Some benches outside if you want to 'eat in' but best bet is to take your food down to the beach for a picnic. ](https://images.trvl-media.com/place/6135676/25271101-6fdf-4e1c-9afc-551d4a7f6b53.jpg?impolicy=fcrop&w=806&h=605&p=1&q=high) Photo by Shobha George ## Top Chilmark Hotel Reviews ![Harbor View Hotel](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/7b9d68f4_y.jpg) ### Harbor View Hotel 10/10 Excellent "Cannot wait to return 😊" [](https://expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) ## Find out more about Chilmark ## Five Star Hotels in Chilmark There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Chilmark so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Chilmark and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Chilmark Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Chilmark The results are in, and Chilmark 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Chilmark! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Chilmark today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Chilmark? > - Search for the lowest price per night from CA $335 ### What makes a hotel 5 stars in Chilmark? ### Are there any 5-star all-inclusive resorts in Chilmark? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [1 Star Hotels in Chappaquiddick Island ](https://www.expedia.ca/1Star-Chappaquiddick-Island-Hotels.s10-0-d6287412.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Orleans ](https://www.expedia.ca/1Star-Orleans-Hotels.s10-0-d142149.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Quaise ](https://www.expedia.ca/1Star-Quaise-Hotels.s10-0-d553248635975748377.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Cape Cod ](https://www.expedia.ca/2Star-Cape-Cod-Hotels.s20-0-d180061.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Martha's Vineyard ](https://www.expedia.ca/2Star-Marthas-Vineyard-Hotels.s20-0-d6047691.Travel-Guide-Filter-Hotels) - 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