Title: Chilmark, MA Cottage Rentals from $416 | Expedia.com [Chilmark Travel Guide](https://expedia.com/Chilmark.dx6135676)[Hotels in Chilmark](https://expedia.com/Chilmark-Hotels.d6135676.Travel-Guide-Hotels)[Vacation Rentals in Chilmark](https://expedia.com/Chilmark-Vacation-Rentals.d6135676.Travel-Guide-VacationRentals)[Flights to Chilmark](https://expedia.com/Cheap-Flights-To-Chilmark.d6135676.Travel-Guide-Flights)[Things to do in Chilmark](https://expedia.com/Things-To-Do-In-Chilmark.d6135676.Travel-Guide-Activities)[Car Rentals in Chilmark](https://expedia.com/Car-Rentals-In-Chilmark.d6135676.Car-Rental-Guide)[Chilmark Vacation Packages](https://expedia.com/Chilmark.d6135676.Destination-Travel-Guides) ![Chilmark Shellfish Department on Martha’s Vineyard](https://images.trvl-media.com/place/6135676/824050a0-a336-4250-9bcd-66c115369156.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6135676/824050a0-a336-4250-9bcd-66c115369156.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=6135676&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6135676&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=6135676&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6135676&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chilmark cottages ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/ad29049f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/70923cac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/324c2c1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/7f904b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming cottage overlooking the bay in Padanaram Village. [](https://www.expedia.com/South-Dartmouth-Hotels-Charming-Cottage-Overlooking-The-Bay-In-Padanaram-Village.h107997278.Hotel-Information) Dartmouth 10/10 Exceptional (11 reviews) "Beautiful cottage ! Immaculately kept! Sunsets at night were amazing to watch. Very comfortable and inviting home. Definitely recommend a nice stay ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ralpjh c. $373 nightly $416 total Feb 7 - Feb 8 Total with taxes and fees [](https://www.expedia.com/South-Dartmouth-Hotels-Charming-Cottage-Overlooking-The-Bay-In-Padanaram-Village.h107997278.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27120000/27117800/27117723/37e0972d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27117800/27117723/925f539a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, beach towels](https://images.trvl-media.com/lodging/28000000/27120000/27117800/27117723/1d390dbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/28000000/27120000/27117800/27117723/424a2e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced [](https://www.expedia.com/Mashpee-Hotels-Charming-Beach-Cottage.h27117723.Hotel-Information) New Seabury 8.6/10 Excellent (91 reviews) "Property needs a refresh." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul B. $539 nightly $617 total Feb 28 - Mar 1 Total with taxes and fees [](https://www.expedia.com/Mashpee-Hotels-Charming-Beach-Cottage.h27117723.Hotel-Information) 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. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-02-19&endDate=2026-02-20®ionId=6135676&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=COTTAGE) Cabins [](https://www.expedia.com/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CABIN) Condos [](https://www.expedia.com/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CONDO) Apartments [](https://www.expedia.com/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=APARTMENT) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=APART_HOTEL) Villas [](https://www.expedia.com/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=VILLA) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChilmark-Cottages.d6135676-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChilmark-Cottages.d6135676-aaCottages.Travel-Guide-Accommodation) ## Top Chilmark Hotel Reviews ![Hampton Inn by Hilton New Bedford/Fairhaven](https://images.trvl-media.com/lodging/1000000/60000/55000/54948/647c4f15_y.jpg) ### Hampton Inn by Hilton New Bedford/Fairhaven 10/10 Excellent "Clean room. Comfortable bed.Great coffee! Friendly staff workers." [](https://expedia.com/Fairhaven-Hotels-Hampton-Inn-By-Hilton-New-BedfordFairhaven.h54948.Hotel-Information) ![The Club at New Seabury](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/4270e26b_y.jpg) ### The Club at New Seabury 10/10 Excellent "Everything was superb, accommodations, check in service, check out service!!" [](https://expedia.com/Mashpee-Hotels-The-Club-At-New-Seabury.h11621632.Hotel-Information) ![Falmouth Inn](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/a26689a2_y.jpg) ### Falmouth Inn 10/10 Excellent "I stay here alot" [](https://expedia.com/Falmouth-Hotels-Falmouth-Inn.h893142.Hotel-Information) ![Falmouth Tides ](https://images.trvl-media.com/lodging/70000000/69380000/69374600/69374512/3742adf6_y.jpg) ### Falmouth Tides 10/10 Excellent "Everything was great except we wish we had a little table in the room. " [](https://expedia.com/Falmouth-Hotels-Falmouth-Tides-Motel.h69374512.Hotel-Information) ![Vineyard Harbor Motel - Private Beach](https://images.trvl-media.com/lodging/61000000/60390000/60384600/60384563/6bd7fc20_y.jpg) ### Vineyard Harbor Motel - Private Beach 10/10 Excellent "Professional Courteous Attentive Clean room and good shower" [](https://expedia.com/Vineyard-Haven-Hotels-Vineyard-Harbor-Motel.h60384563.Hotel-Information) ![Inn on the Square](https://images.trvl-media.com/lodging/1000000/10000/10000/9953/27ed2889_y.jpg) ### Inn on the Square 10/10 Excellent "Familiar hotel " [](https://expedia.com/Falmouth-Hotels-Inn-On-The-Square.h9953.Hotel-Information) ![The Coonamessett](https://images.trvl-media.com/lodging/7000000/6600000/6591200/6591194/4add9b13_y.jpg) ### The Coonamessett 10/10 Excellent "The room was spacious and lovely. The room was extremely clean. The staff was friendly. The breakfast had a lovely variety including healthy options. The woman who was serving breakfast was friendly and helpful. The grounds were pretty. Our only disappointment was the noise from several trucks nearby (it sounded like the parking lot and behind us) that sounded like they were unloading things extremely early (around 4 am)." [](https://expedia.com/Falmouth-Hotels-The-Coonamessett.h6591194.Hotel-Information) ![Mansion House Inn And Spa](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/e86ce24b_y.jpg) ### Mansion House Inn And Spa 10/10 Excellent "Spotless, beautiful room with comfortable bed, and welcoming staff through the inn. Also, very close to the ferry and shops/restaurants; ideal location. Would definitely stay here again (and again)!" [](https://expedia.com/Vineyard-Haven-Hotels-Mansion-House-Inn-And-Spa.h2182094.Hotel-Information) ![InnSeason Resorts Surfside](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154024/d2448752_y.jpg) ### InnSeason Resorts Surfside 10/10 Excellent "Room was clean, beautiful view, loved the hot tub in the room, and staff was very friendly and always willing to help. " [](https://expedia.com/East-Falmouth-Hotels-InnSeason-Resorts-Surfside.h1154024.Hotel-Information) ## Find out more about Chilmark ## Chilmark Cottages information | Number of reviews | 96 | | ----------------- | ------------ | | Accommodation | 153 Cottages | | Lowest Price | $416 | | Highest Price | $617 | ## Frequently asked questions ### How much do cottages in Chilmark cost? ### Why book your cottage in Chilmark with Expedia? ### How can I find cheap cottages in Chilmark? ### What is there to do in Chilmark near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotels near Chilmark Chocolates ](https://www.expedia.com/Chilmark-Chocolates-Hotels.0-l553248621532666149-0.Travel-Guide-Filter-Hotels) - [B&B in Menemsha ](https://www.expedia.com/Menemsha-Bed-And-Breakfast.d6060685-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Menemsha ](https://www.expedia.com/Menemsha-Cottages.d6060685-aaCottages.Travel-Guide-Accommodation) - 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