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) ![In the fishing village of Menemsha in Marthas Vineyard. Delicious lobster rolls, clam chowder, lobster bisque etc. they'll boil your fresh lobster for you if you don't want to do it yourself. Some benches outside if you want to 'eat in' but best bet is to take your food down to the beach for a picnic. ](https://images.trvl-media.com/place/6135676/25271101-6fdf-4e1c-9afc-551d4a7f6b53.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Shobha George # Find Hotels with a Pool in Chilmark, MA from CA $171 - ![](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 [Jan 2 - Jan 3](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-01-02&endDate=2026-01-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 3 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-01-03&endDate=2026-01-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6135676&startDate=2026-01-09&endDate=2026-01-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chilmark hotels with a pool ![Seasonal outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/3348dea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/36a1f0b0.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) ![Seasonal outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/f0ed7d64.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 (343) "Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose O. CA $198 CA $227 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Mashpee-Hotels-The-Club-At-New-Seabury.h11621632.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) ![Hallway](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/c832e252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/ba60e8de.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) ### Falmouth Inn [](https://www.expedia.ca/Falmouth-Hotels-Falmouth-Inn.h893142.Hotel-Information) Falmouth 8.0/10 Very good (1000) "Clean room, good shower and helpful staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $129 CA $176 total includes taxes & fees Jan 12 - Jan 13 [](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) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/12000/11989/b77771b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/12000/11989/63513190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12000/11989/d05815b1.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 (160) "Very good " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Welington CA $149 CA $171 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Falmouth-Hotels-Hotel-Cape-Cod.h11989.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) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1280000/1279900/1279850/cbad7255.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1280000/1279900/1279850/64d1c0e2.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 (373) "Short overnight stay. Big clean rooms and comfortable beds. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $137 CA $173 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Falmouth-Hotels-Admiralty-Inn-Suites.h1279850.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/4000000/3600000/3592900/3592874/70add531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3600000/3592900/3592874/1f27df8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/4000000/3600000/3592900/3592874/84bcc25b.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 (449) "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 $184 CA $210 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Falmouth-Hotels-ShoreWay-Acres-Inn-Cape-Cod-Lodging.h3592874.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/10000/9953/aa02dacb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/10000/9953/554c64cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch served; American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/10000/10000/9953/w1280h882x0y8-1138e6a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/10000/9953/78ad9652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn on the Square [](https://www.expedia.ca/Falmouth-Hotels-Inn-On-The-Square.h9953.Hotel-Information) Falmouth 8.6/10 Excellent (1002) "Great location Comfortable beds Reasonably price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $148 CA $202 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Falmouth-Hotels-Inn-On-The-Square.h9953.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/65350001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/a3da66ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/ce22346a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/910c8a68.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 (195) "Best scenery ever !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline CA $160 CA $183 total includes taxes & fees Jan 7 - Jan 8 [](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) ![1 bedroom, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/60000/55000/54948/647c4f15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/60000/55000/54948/0fae0ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/60000/55000/54948/c84111b8.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 (1003) "courteous staff, clean room, quiet" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gail CA $159 CA $178 total includes taxes & fees Jan 9 - Jan 10 [](https://www.expedia.ca/Fairhaven-Hotels-Hampton-Inn-By-Hilton-New-BedfordFairhaven.h54948.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/f30d9b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/ec427f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/d7a18547.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) ### 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 (1000) "Our second time staying. Friendly staff, perfect location, great views. Highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kurt CA $238 CA $286 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Vineyard-Haven-Hotels-Mansion-House-Inn-And-Spa.h2182094.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/b242e02b.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/8ca88d65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/3c648f42.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 (1000) "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=2026-01-16&endDate=2026-01-17®ionId=6135676&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chilmark Hotel Reviews ![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 "Spacious bedroom. " [](https://expedia.ca/Falmouth-Hotels-Admiralty-Inn-Suites.h1279850.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 "Our second time staying. Friendly staff, perfect location, great views. Highly recommend." [](https://expedia.ca/Vineyard-Haven-Hotels-Mansion-House-Inn-And-Spa.h2182094.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 "Staff was very friendly! " [](https://expedia.ca/North-Falmouth-Hotels-Sea-Crest-Beach-Hotel.h25567.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 "This was our 2nd stay. We stay here when visiting family in December. Hotel is clean, comfortable and quiet. Bathroom is spacious. Very easy to walk town. " [](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 "Should add hand rails in shower/tub" [](https://expedia.ca/Fairhaven-Hotels-Hampton-Inn-By-Hilton-New-BedfordFairhaven.h54948.Hotel-Information) ![InnSeason Resorts HarborWalk](https://images.trvl-media.com/lodging/1000000/10000/3000/2974/e1718fd5_y.jpg) ### InnSeason Resorts HarborWalk 10/10 Excellent "Great experience. Nice staff" [](https://expedia.ca/Falmouth-Hotels-InnSeason-Resorts-HarborWalk.h2974.Hotel-Information) ![Faraway Martha's Vineyard](https://images.trvl-media.com/lodging/1000000/70000/65700/65623/10e4fb42_y.jpg) ### Faraway Martha's Vineyard 10/10 Excellent "Very cozy comfortable hotel!!" [](https://expedia.ca/Edgartown-Hotels-Faraway-Marthas-Vineyard.h65623.Hotel-Information) ![Falmouth Inn](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/a26689a2_y.jpg) ### Falmouth Inn 10/10 Excellent "Clean room, amenities, indoor pool " [](https://expedia.ca/Falmouth-Hotels-Falmouth-Inn.h893142.Hotel-Information) ![Harbor View Hotel](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/7b9d68f4_y.jpg) ### Harbor View Hotel 10/10 Excellent "Cannot wait to return 😊" [](https://expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.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) - 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