Title: Book the Best Hotels with POOL in Chilmark in 2026 | 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 availability on Chilmark Hotels with a Pool Tonight [Feb 17 - Feb 18](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-02-17&endDate=2026-02-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 18 - Feb 19](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-02-18&endDate=2026-02-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-02-20&endDate=2026-02-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-02-27&endDate=2026-03-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chilmark hotels with a pool ![Private beach nearby, beach bar](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/0e09af58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/c3910e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/481dceb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/d67fc379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Club at New Seabury [](https://www.expedia.ca/Mashpee-Hotels-The-Club-At-New-Seabury.h11621632.Hotel-Information) New Seabury 9.0/10 Wonderful (350 reviews) "Everything was superb, accommodations, check in service, check out service!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dianna CA $201 CA $230 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Mashpee-Hotels-The-Club-At-New-Seabury.h11621632.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/32247115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/b950a23c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/bdde1267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/2385000d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mansion House Inn And Spa [](https://www.expedia.ca/Vineyard-Haven-Hotels-Mansion-House-Inn-And-Spa.h2182094.Hotel-Information) Vineyard Haven 9.4/10 Exceptional (1,000 reviews) "My favorite place to stay on the Island! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $237 CA $284 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Vineyard-Haven-Hotels-Mansion-House-Inn-And-Spa.h2182094.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/30000/25600/25567/1fc9f4bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/30000/25600/25567/9c451226.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Oceanfront](https://images.trvl-media.com/lodging/1000000/30000/25600/25567/a0e3a329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/25600/25567/c3420944.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea Crest Beach Resort [](https://www.expedia.ca/North-Falmouth-Hotels-Sea-Crest-Beach-Hotel.h25567.Hotel-Information) North Falmouth 8.0/10 Very good (251 reviews) "Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Felix CA $138 CA $236 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/North-Falmouth-Hotels-Sea-Crest-Beach-Hotel.h25567.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/e319d793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Accessible](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/339f4ae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/3f32a5de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/9f2f620c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Falmouth Inn [](https://www.expedia.ca/Falmouth-Hotels-Falmouth-Inn.h893142.Hotel-Information) Falmouth 8.0/10 Very good (1,001 reviews) "I stay here alot" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ronan CA $137 CA $185 total includes taxes & fees Feb 24 - Feb 25 [](https://www.expedia.ca/Falmouth-Hotels-Falmouth-Inn.h893142.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/12000/11989/85b80a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/12000/11989/66889665.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served](https://images.trvl-media.com/lodging/1000000/20000/12000/11989/fe097a20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/12000/11989/aec4f7ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Iris Hotel Cape Cod [](https://www.expedia.ca/Falmouth-Hotels-Hotel-Cape-Cod.h11989.Hotel-Information) Falmouth 8.6/10 Excellent (181 reviews) "The Good: Clean room, friendly staff, fast check in, vaulted ceiling, confortable bed, quiet. Not so good: Breakfast food was awful, very dim bathroom lighting. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $146 CA $167 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/Falmouth-Hotels-Hotel-Cape-Cod.h11989.Hotel-Information) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3600000/3592900/3592874/230a23d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3600000/3592900/3592874/8314806b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room](https://images.trvl-media.com/lodging/4000000/3600000/3592900/3592874/403ecda3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/4000000/3600000/3592900/3592874/ebed4240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ShoreWay Acres Inn & Cape Cod Lodging [](https://www.expedia.ca/Falmouth-Hotels-ShoreWay-Acres-Inn-Cape-Cod-Lodging.h3592874.Hotel-Information) Falmouth 8.4/10 Very good (450 reviews) "Very good for a lower priced motel/inn. Two minutes walk into town, so very convenient. Easy to park. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne Monique CA $182 CA $209 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Falmouth-Hotels-ShoreWay-Acres-Inn-Cape-Cod-Lodging.h3592874.Hotel-Information) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1280000/1279900/1279850/13951ac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (2 King Beds, Townhouse, Smoke Free)](https://images.trvl-media.com/lodging/2000000/1280000/1279900/1279850/b50603f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1280000/1279900/1279850/64d1c0e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Jetted Tub (Smoke Free)](https://images.trvl-media.com/lodging/2000000/1280000/1279900/1279850/ccfd7232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Admiralty Inn & Suites - a Red Collection Hotel [](https://www.expedia.ca/Falmouth-Hotels-Admiralty-Inn-Suites.h1279850.Hotel-Information) East Falmouth 8.8/10 Excellent (382 reviews) "Short overnight stay. Big clean rooms and comfortable beds. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $142 CA $179 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Falmouth-Hotels-Admiralty-Inn-Suites.h1279850.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/fa5d1d1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/7f6b1d68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/fcdb2776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/23bd3a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### InnSeason Resorts Captain's Quarters [](https://www.expedia.ca/Falmouth-Hotels-InnSeason-Resorts-Captains-Quarters.h1154022.Hotel-Information) Falmouth Heights 9.8/10 Exceptional (199 reviews) "This is my go to hotel when I’m in Falmouth. Always clean and the staff are very friendly. The one bedroom units are very nice!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff CA $177 CA $202 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Falmouth-Hotels-InnSeason-Resorts-Captains-Quarters.h1154022.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/60000/55000/54948/0dab3d80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gym](https://images.trvl-media.com/lodging/1000000/60000/55000/54948/b39a2f00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/60000/55000/54948/3adc333d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible, Non Smoking](https://images.trvl-media.com/lodging/1000000/60000/55000/54948/149bf2ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton New Bedford/Fairhaven [](https://www.expedia.ca/Fairhaven-Hotels-Hampton-Inn-By-Hilton-New-BedfordFairhaven.h54948.Hotel-Information) Fairhaven 8.8/10 Excellent (1,001 reviews) "Check in was quick, staff was friendly and knowledgeable, room was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $146 CA $163 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Fairhaven-Hotels-Hampton-Inn-By-Hilton-New-BedfordFairhaven.h54948.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/3f1a493f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden view](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/b0e1e614.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/fc5aa5e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/7c321ede.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 (1,001 reviews) "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) 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=2026-03-03&endDate=2026-03-04®ionId=6135676&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Chilmark Breakfast included 4 stars Ocean view 5 stars Hot tub ![](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=AFFINITY_SPRING_PROMO_6135676) ## 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 "Room was great. Staff was excellent. Breakfast was delicious. Thank you" [](https://expedia.ca/Falmouth-Hotels-Hotel-Cape-Cod.h11989.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 "We always stay here when visiting Falmouth. Extremely friendly staff. We travel with a service dog and the setting is convenient to walking him, and good lighting as we walk. Feel very welcomed and safe in the location. The room was clean, and all requests for additional items we needed was met quickly and happily. We won”’t stay anywhere else when in the area!!" [](https://expedia.ca/Falmouth-Hotels-Inn-On-The-Square.h9953.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) ![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) ![Mariner Motel](https://images.trvl-media.com/lodging/5000000/4560000/4555100/4555042/01f382c5_y.jpg) ### Mariner Motel 10/10 Excellent "Clean, comfortable bed, easy check in and check out" [](https://expedia.ca/Falmouth-Hotels-Mariner-Motel.h4555042.Hotel-Information) ![Sea Crest Beach Resort](https://images.trvl-media.com/lodging/1000000/30000/25600/25567/19fd0067_y.jpg) ### Sea Crest Beach Resort 10/10 Excellent "Great location." [](https://expedia.ca/North-Falmouth-Hotels-Sea-Crest-Beach-Hotel.h25567.Hotel-Information) ![Admiralty Inn & Suites - a Red Collection Hotel](https://images.trvl-media.com/lodging/2000000/1280000/1279900/1279850/64d1c0e2_y.jpg) ### Admiralty Inn & Suites - a Red Collection Hotel 10/10 Excellent "Heat wasn’t working even after switching rooms but other than that it was a great stay." [](https://expedia.ca/Falmouth-Hotels-Admiralty-Inn-Suites.h1279850.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Chilmark? ### What is there to see and do in Chilmark? ### When is the best time to book a hotel with a pool in Chilmark? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Other - More ways to book - [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) - [Guest Houses in Aquinnah ](https://www.expedia.ca/Aquinnah-Guest-Houses.d553248634998599060-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Aquinnah ](https://www.expedia.ca/Aquinnah-Holiday-Parks.d553248634998599060-aaHolidayParks.Travel-Guide-Accommodation) - [Hotels with a Pool in Aquinnah ](https://www.expedia.ca/Aquinnah-Hotels-Hotel-With-Pool.0-0-d553248634998599060-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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