Title: Chilmark Cottages from CA $590 | Expedia.ca [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)[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) ![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__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 prices for these dates In two weeks [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-06-05&endDate=2026-06-07&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) ![Interior](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/7f904b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/108000000/107997300/107997278/da383bf5.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) ### Charming cottage overlooking the bay in Padanaram Village. [](https://www.expedia.ca/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. CA $335 CA $590 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/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.ca/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. CA $407 CA $833 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-02-26&endDate=2026-02-27®ionId=6135676&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_6135676) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CONDO) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=APART_HOTEL) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=VILLA) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chilmark%2C+Massachusetts%2C+United+States+of+America®ionId=6135676&latLong=41.34317%2C-70.744751&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CABIN) ![](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%2FChilmark-Cottages.d6135676-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChilmark-Cottages.d6135676-aaCottages.Travel-Guide-Accommodation) ## Top Chilmark Hotel Reviews ![Iris Hotel Cape Cod ](https://images.trvl-media.com/lodging/1000000/20000/12000/11989/63513190_y.jpg) ### Iris Hotel Cape Cod 10/10 Excellent "The bed was so comfortable. Towels thick and luxurious! Had an E station for my electric car." [](https://expedia.ca/Falmouth-Hotels-Hotel-Cape-Cod.h11989.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 "Friendly staff, nice clean room" [](https://expedia.ca/Vineyard-Haven-Hotels-Vineyard-Harbor-Motel.h60384563.Hotel-Information) ![Falmouth Tides ](https://images.trvl-media.com/lodging/70000000/69380000/69374600/69374512/3742adf6_y.jpg) ### Falmouth Tides 10/10 Excellent "Yes and yes. The room was absolutely spotless and the receptionist, Sierra, could not have been more pleasant. We had an off-season balcony, ocean view room, and it, together with the town of Falmouth was absolutely charming. A delightful midweek escape." [](https://expedia.ca/Falmouth-Hotels-Falmouth-Tides-Motel.h69374512.Hotel-Information) ![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.ca/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.ca/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.ca/Falmouth-Hotels-Falmouth-Inn.h893142.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.ca/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.ca/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.ca/Vineyard-Haven-Hotels-Mansion-House-Inn-And-Spa.h2182094.Hotel-Information) ## Find out more about Chilmark ## Chilmark Cottages information | Number of reviews | 11 | | ----------------- | ------------ | | Accommodation | 153 Cottages | | Lowest Price | CA $590 | | Highest Price | CA $833 | ## 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 Rental - Other - More ways to book - [3 Star Hotels in Martha's Vineyard ](https://www.expedia.ca/3Star-Marthas-Vineyard-Hotels.s30-0-d6047691.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Martha's Vineyard ](https://www.expedia.ca/4Star-Marthas-Vineyard-Hotels.s40-0-d6047691.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Martha's Vineyard ](https://www.expedia.ca/5Star-Marthas-Vineyard-Hotels.s50-0-d6047691.Travel-Guide-Filter-Hotels) - 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