Title: Book the Best Hotels with POOL in Chilmark in 2025 | 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. # Find Hotels with a Pool in Chilmark, MA ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Hotels with a Pool Tonight [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-10-02&endDate=2025-10-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-10-03&endDate=2025-10-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-10-03&endDate=2025-10-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chilmark Hotels with a Pool ## Top Chilmark Hotel Reviews ![Iris Hotel Cape Cod ](//images.trvl-media.com/lodging/1000000/20000/12000/11989/63513190_y.jpg) ### Iris Hotel Cape Cod 10/10 Excellent "Floor needs cleaning" [](https://expedia.ca/Falmouth-Hotels-Hotel-Cape-Cod.h11989.Hotel-Information) ![Falmouth Inn](//images.trvl-media.com/lodging/1000000/900000/893200/893142/a26689a2_y.jpg) ### Falmouth Inn 10/10 Excellent "We attened an event very close ny at a marina. We were able to park and walk. Hotel has a restaurant and bar, but lots of options withinn walking distsnce. Close to main street shopping with lots of shops and restaurants. Not a big deal, but we arrivrd at 1pm, check in is at 3pm. Our room was ready but they said $20 extra to check in early, we just left our truck and went out and came back later for our keys. Room was clean. Bed was comfortable. Its a basic hotel, we would stay again " [](https://expedia.ca/Falmouth-Hotels-Falmouth-Inn.h893142.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 "The staff were " [](https://expedia.ca/Falmouth-Hotels-Inn-On-The-Square.h9953.Hotel-Information) ![Faraway Martha's Vineyard](//images.trvl-media.com/lodging/1000000/70000/65700/65623/10e4fb42_y.jpg) ### Faraway Martha's Vineyard 10/10 Excellent "Great location, clean hotel, walkable to everything in edgartown" [](https://expedia.ca/Edgartown-Hotels-Faraway-Marthas-Vineyard.h65623.Hotel-Information) ![Admiralty Inn & Suites - a Red Collection Hotel](//images.trvl-media.com/lodging/2000000/1280000/1279900/1279850/64d1c0e2_y.jpg) ### Admiralty Inn & Suites - a Red Collection Hotel 10/10 Excellent "Did not use gym." [](https://expedia.ca/Falmouth-Hotels-Admiralty-Inn-Suites.h1279850.Hotel-Information) ![The Club at New Seabury](//images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/4270e26b_y.jpg) ### The Club at New Seabury 10/10 Excellent "Stayed in one of the cottages. It was so cute. Had everything you needed. Only stood overnight wished we had more time. " [](https://expedia.ca/Mashpee-Hotels-The-Club-At-New-Seabury.h11621632.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 "Loved the beach view from ocean front rooms. Clean , beds comfortable, loved new shower. They now only offer 2 small bottles of water for whole stay Use to be be 2, daily." [](https://expedia.ca/North-Falmouth-Hotels-Sea-Crest-Beach-Hotel.h25567.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 "Great hotel on the island with history" [](https://expedia.ca/Vineyard-Haven-Hotels-Mansion-House-Inn-And-Spa.h2182094.Hotel-Information) ![Harbor View Hotel](//images.trvl-media.com/lodging/1000000/10000/8600/8504/7b9d68f4_y.jpg) ### Harbor View Hotel 10/10 Excellent "The staff was amazing. Everyone was friendly and willing to help you with anything, from dinner recommendations, sites to see, parking, helping with bags and helping to install the top on my jeep." [](https://expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Chilmark? > [Iris Hotel Cape Cod](https://www.expedia.ca/Falmouth-Hotels-Hotel-Cape-Cod.h11989.Hotel-Information): Offers a snack bar/deli, an indoor pool, and free self parking. [Falmouth Inn](https://www.expedia.ca/Falmouth-Hotels-Falmouth-Inn.h893142.Hotel-Information): Provides daily, a pool, and free self parking. [Sea Crest Beach Resort](https://www.expedia.ca/North-Falmouth-Hotels-Sea-Crest-Beach-Hotel.h25567.Hotel-Information): Hotel, 2-minute walk from Cape Cod Beaches. Features a children's pool, a seasonal outdoor pool, and a private beach. [Inn on the Square](https://www.expedia.ca/Falmouth-Hotels-Inn-On-The-Square.h9953.Hotel-Information): Offers complimentary wireless internet access, an indoor pool, and televisions. [Summercamp](https://www.expedia.ca/Oak-Bluffs-Hotels-Summercamp.h10058501.Hotel-Information): Provides 2 restaurants, a seasonal outdoor pool, and complimentary wired internet access. ### What is there to see and do in Chilmark? > The picturesque setting of Menemsha Beach and Lucy Vincent Beach showcase the area's natural beauty. During your stay, check out sights such as Chilmark Town Hall, Chilmark Public Library, and Chilmark Chocolates. ### When is the best time to book a hotel with a pool in Chilmark? > Taking into account the local weather in Chilmark can help you maximize your time at the pool during your trip. 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. 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[Luxury Hotels in West Tisbury](https://www.expedia.ca/West-Tisbury-Hotels-Luxury-Hotel.0-0-d3000007836-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in West Tisbury](https://www.expedia.ca/West-Tisbury-Hotels-Shopping-Hotel.0-0-d3000007836-tShoppingHotel.Travel-Guide-Filter-Hotels) - [West Tisbury Hotels](https://www.expedia.ca/West-Tisbury-Hotels.d3000007836.Travel-Guide-Hotels) - [Houseboats in West Tisbury](https://www.expedia.ca/West-Tisbury-Houseboats.d3000007836-aaHouseboats.Travel-Guide-Accommodation) - [Inns in West Tisbury](https://www.expedia.ca/West-Tisbury-Inns.d3000007836-aaInns.Travel-Guide-Accommodation) - [Flights from Aquinnah](https://www.expedia.ca/lp/flights/553248634998599060/flights-from-aquinnah) - [Visit Aquinnah](https://www.expedia.ca/Aquinnah.dx553248634998599060) - [Things to do in Menemsha](https://www.expedia.ca/Things-To-Do-In-Menemsha.d6060685.Travel-Guide-Activities) - [Book Hotels with a Pool in Chilmark on Expedia.com](https://www.expedia.com/Chilmark-Hotels-Hotel-With-Pool.0-0-d6135676-tHotelwithPool.Travel-Guide-Filter-Hotels)