Title: Chilmark Guest Houses from CA $251 | 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) ![](https://mediaim.expedia.com/destination/2/92660841fb017fb68076d67660f760a8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Wen C. # Search Guest Houses in Chilmark from CA $251 ![](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 Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chilmark Guest Houses ![Exterior](https://images.trvl-media.com/lodging/12000000/11180000/11172600/11172592/d11aa513.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 Queen Bed with Sofa bed | Living area](https://images.trvl-media.com/lodging/12000000/11180000/11172600/11172592/27eb2c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 1 King Bed with Sofa bed | Private kitchen](https://images.trvl-media.com/lodging/12000000/11180000/11172600/11172592/430aaed8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 Queen Bed with Sofa bed | Private kitchen](https://images.trvl-media.com/lodging/12000000/11180000/11172600/11172592/d22dc480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lightkeepers Inn Edgartown 9.4/10 Exceptional (204) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin CA $225 CA $251 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Edgartown-Hotels-The-Lightkeepers-Inn.h11172592.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/w2388h1514x0y77-1097f3b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/0fb3af2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/a1cc2110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Video games, books, video library](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/w2323h1742x204y153-3585a9ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Estate with salt water pool & pond with kayaks Oak Bluffs CA $3,499 CA $5,644 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Oak-Bluffs-Hotels-Beautiful-Estate-With-Salt-Water-Pool-Pond-With-Kayaks.h54935241.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=2025-11-08&endDate=2025-11-09®ionId=6135676&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](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-Guest-Houses.d6135676-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChilmark-Guest-Houses.d6135676-aaGuestHouses.Travel-Guide-Accommodation) ## Top Chilmark Hotel Reviews ![AutoCamp Cape Cod](//images.trvl-media.com/lodging/50000000/49180000/49175900/49175859/3458b4d1_y.jpg) ### AutoCamp Cape Cod 10/10 Excellent "The property is beautiful very well set up the airstreams are also very well set up with air conditioning and heat. Great place to get away from the stresses of life" [](https://expedia.ca/Falmouth-Hotels-AutoCamp-Cape-Cod.h49175859.Hotel-Information) ![Mansion House Inn And Spa](//images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/e86ce24b_y.jpg) ### Mansion House Inn And Spa 10/10 Excellent "Overall, a great stay. We only stayed one night so didn't get to enjoy all the amenities but the staff was super friendly and informative, and they provided us with a fan and extra pillows when asked. We will certainly stay there again in the future should we visit MV again. " [](https://expedia.ca/Vineyard-Haven-Hotels-Mansion-House-Inn-And-Spa.h2182094.Hotel-Information) ![Inn on the Square](//images.trvl-media.com/lodging/1000000/10000/10000/9953/27ed2889_y.jpg) ### Inn on the Square 10/10 Excellent "Very pleased with everything I " [](https://expedia.ca/Falmouth-Hotels-Inn-On-The-Square.h9953.Hotel-Information) ![Summercamp](//images.trvl-media.com/lodging/11000000/10060000/10058600/10058501/4ff1c19a_y.jpg) ### Summercamp 10/10 Excellent "There is a unique charm to the building, inside and out. The Living Room instead of a Lobby, the dining area with coffee set up- a place to enjoy a coffee or take out meal with a beautiful ocean view. Our room was charming and clean. The office staff was helpful with directions, bus schedules, suggesting restaurants, offering to help us w/ luggage up and down stairs, setting up taxis for us and more. We loved our stay. " [](https://expedia.ca/Oak-Bluffs-Hotels-Summercamp.h10058501.Hotel-Information) ![Sea Crest Beach Resort](//images.trvl-media.com/lodging/1000000/30000/25600/25567/19fd0067_y.jpg) ### Sea Crest Beach Resort 10/10 Excellent "The lady working the desk when we ck’d in was excellent. Very helpful, friendly & informative. Our beach view was perfect. Enjoyed a beautiful sunset." [](https://expedia.ca/North-Falmouth-Hotels-Sea-Crest-Beach-Hotel.h25567.Hotel-Information) ![Iris Hotel Cape Cod ](//images.trvl-media.com/lodging/1000000/20000/12000/11989/63513190_y.jpg) ### Iris Hotel Cape Cod 10/10 Excellent "Clean room" [](https://expedia.ca/Falmouth-Hotels-Hotel-Cape-Cod.h11989.Hotel-Information) ![Hampton Inn by Hilton New Bedford/Fairhaven](//images.trvl-media.com/lodging/1000000/60000/55000/54948/647c4f15_y.jpg) ### Hampton Inn by Hilton New Bedford/Fairhaven 10/10 Excellent "This is my favorite hotel in the area" [](https://expedia.ca/Fairhaven-Hotels-Hampton-Inn-By-Hilton-New-BedfordFairhaven.h54948.Hotel-Information) ![Vineyard Harbor Motel - Private Beach](//images.trvl-media.com/lodging/61000000/60390000/60384600/60384563/6bd7fc20_y.jpg) ### Vineyard Harbor Motel - Private Beach 10/10 Excellent "We stayed here for an overnight and were pleasantly surprised by this motel. It is a basic accommodation, but very clean with a comfortable bed free coffee, great location and very reasonably priced. We will certainly stay here again in the future. Highly recommend it for the price!" [](https://expedia.ca/Vineyard-Haven-Hotels-Vineyard-Harbor-Motel.h60384563.Hotel-Information) ![Harbor View Hotel](//images.trvl-media.com/lodging/1000000/10000/8600/8504/7b9d68f4_y.jpg) ### Harbor View Hotel 10/10 Excellent "The area was safe and the dining experience was great. " [](https://expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) ## Find out more about Chilmark ## Chilmark Guest Houses information | Number of reviews | 204 | | --- | --- | | Accommodation | 6 Guest Houses | | Lowest Price | CA $251 | | Highest Price | CA $5,644 | ## 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) - [Aparthotels in Aquinnah](https://www.expedia.ca/Aquinnah-Apart-Hotels.d553248634998599060-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Aquinnah](https://www.expedia.ca/Aquinnah-Bed-And-Breakfast.d553248634998599060-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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