Title: Book the Best Hotels with POOL in Winthrop in 2026 | Expedia.ca [Winthrop Travel Guide](https://expedia.ca/Winthrop.dx175875)[Hotels in Winthrop](https://expedia.ca/Winthrop-Hotels.d175875.Travel-Guide-Hotels)[Vacation Rentals in Winthrop](https://expedia.ca/Winthrop-Vacation-Rentals.d175875.Travel-Guide-VacationRentals)[Flights to Winthrop](https://expedia.ca/Cheap-Flights-To-Winthrop.d175875.Travel-Guide-Flights)[Winthrop Car Rentals](https://expedia.ca/Car-Rentals-In-Winthrop.d175875.Car-Rental-Guide)[Winthrop Vacation Packages](https://expedia.ca/Winthrop.d175875.Destination-Travel-Guides) ![Historic Water Tower at the coast in Winthrop Head in town of Winthrop, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175875/0fab3468-aede-4870-9973-b6fa1f9d84fc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Winthrop, MA from CA $189 - ![](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 Winthrop Hotels with a Pool Tonight [Jan 10 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=175875&startDate=2026-01-10&endDate=2026-01-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 11 - Jan 12](https://www.expedia.ca/Hotel-Search?regionId=175875&startDate=2026-01-11&endDate=2026-01-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=175875&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=175875&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winthrop hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/e07ab872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/f43a68cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/3a90f50b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seaport Hotel Boston [](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) Seaport District 9.6/10 Exceptional (3,877 reviews) "Great accommodations and friendly staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas CA $167 CA $242 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/c50bac3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/d6de0f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/116c5658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/2d0dd8e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft by Marriott, Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-Aloft-Boston-Seaport-District.h11263952.Hotel-Information) Seaport District 9.0/10 Wonderful (1,397 reviews) "Clean room, great bar and breakfast options and good location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bianca CA $149 CA $214 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Boston-Hotels-Aloft-Boston-Seaport-District.h11263952.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/w3840h2495x0y3-de7291b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/7f0cccc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/w2557h3837x3y3-ca2d3d94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/866dc285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Boston [](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) Downtown Boston 9.0/10 Wonderful (1,777 reviews) "Wonderful stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sujata CA $176 CA $254 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) ![Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/25300/25280/d045bec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/30000/25300/25280/c1fad6f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/25300/25280/e3bedf47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, Japanese cuisine](https://images.trvl-media.com/lodging/1000000/30000/25300/25280/6c59327a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Verb Hotel [](https://www.expedia.ca/Boston-Hotels-The-Verb-Hotel.h25280.Hotel-Information) Fenway–Kenmore 9.6/10 Exceptional (1,981 reviews) "This hotel is quirky and awesome. Loved our stay tremendously. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Irene CA $124 CA $208 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Boston-Hotels-The-Verb-Hotel.h25280.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/98a96315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/ef05180d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/e8e42358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/4f4d7c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Seaport.h55421972.Hotel-Information) Seaport District 9.2/10 Wonderful (2,784 reviews) "Excellent hotel and stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ana CA $175 CA $204 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Seaport.h55421972.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/57000000/56290000/56289400/56289302/95e5db73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/57000000/56290000/56289400/56289302/9e29ca3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/57000000/56290000/56289400/56289302/647818b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/57000000/56290000/56289400/56289302/38218ff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-Homewood-Suites-By-Hilton-Boston-Seaport.h56289302.Hotel-Information) Seaport District 9.2/10 Wonderful (1,414 reviews) "Clean, good breakfast, location is good too" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carla CA $164 CA $189 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Boston-Hotels-Homewood-Suites-By-Hilton-Boston-Seaport.h56289302.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11270000/11264100/11264010/cda52efb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11270000/11264100/11264010/f525b774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/12000000/11270000/11264100/11264010/6a0ac84d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/12000000/11270000/11264100/11264010/5ff5610a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element by Marriott, Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-Element-Boston-Seaport-District.h11264010.Hotel-Information) Seaport District 9.0/10 Wonderful (1,001 reviews) "Everything about the hotel was great and will be staying again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zuri CA $148 CA $207 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Boston-Hotels-Element-Boston-Seaport-District.h11264010.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/a41b9393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast served](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/bc3320d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/89bc4993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/d1e2c1a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omni Boston Hotel at the Seaport [](https://www.expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) Seaport District 9.2/10 Wonderful (4,366 reviews) "Good place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $218 CA $310 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/c874e48e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/60cb4bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/65b5aa9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/b920b61e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-The-Westin-Boston-Seaport-District.h1450057.Hotel-Information) Seaport District 9.2/10 Wonderful (2,359 reviews) "Great staff, excellent room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne CA $211 CA $310 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Boston-Hotels-The-Westin-Boston-Seaport-District.h1450057.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1780000/1778200/1778190/caca53a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 Bedroom](https://images.trvl-media.com/lodging/2000000/1780000/1778200/1778190/31136a5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/2000000/1780000/1778200/1778190/b27fa32d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, minibar, in-room safe](https://images.trvl-media.com/lodging/2000000/1780000/1778200/1778190/b22783ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renaissance® Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-Renaissance-Boston-Waterfront-Hotel.h1778190.Hotel-Information) Seaport District 9.0/10 Wonderful (1,001 reviews) "Staff was very friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jean CA $181 CA $267 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Boston-Hotels-Renaissance-Boston-Waterfront-Hotel.h1778190.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=2026-01-24&endDate=2026-01-25®ionId=175875&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winthrop Hotel Reviews ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Room was cleaned, staff top notch and it was a perfect way " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Hyatt Regency Boston](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/24991d94_y.jpg) ### Hyatt Regency Boston 10/10 Excellent "Really nice hotel, great clean rooms, nice bath, super location, staff were great" [](https://expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Boston Somerville](https://images.trvl-media.com/lodging/1000000/550000/544200/544112/5c021408_y.jpg) ### La Quinta Inn & Suites by Wyndham Boston Somerville 10/10 Excellent "awesome and reasonable price" [](https://expedia.ca/Boston-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Boston-Somerville.h544112.Hotel-Information) ![Hilton Boston Back Bay](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/f418fbdd_y.jpg) ### Hilton Boston Back Bay 10/10 Excellent "Great" [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Back-Bay.h5928.Hotel-Information) ![The Westin Copley Place, Boston, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/10000/4500/4443/ac4901eb_y.jpg) ### The Westin Copley Place, Boston, a Marriott Hotel 10/10 Excellent "Room was great and staff very helpful" [](https://expedia.ca/Boston-Hotels-The-Westin-Copley-Place.h4443.Hotel-Information) ![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg) ### Hilton Boston Logan Airport 10/10 Excellent "Great!" [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "We love to stay at the seaport. The rooms and all the areas are very clean. The hotel was tastefully decorated for the holidays. Our only issue was with the restaurant in the hotel. We tried to get dinner but we sat for over 15/20 minutes without any service. We opted to leave. Otherwise our stay was great. " [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![The Newbury Boston](https://images.trvl-media.com/lodging/1000000/10000/400/395/de8ba46e_y.jpg) ### The Newbury Boston 10/10 Excellent "Staff was friendly and flexible ! Rooms were spacious and beautiful, the housekeeping was not as clean or organized or detailed as other places I’ve been to but still good " [](https://expedia.ca/Boston-Hotels-The-Newbury-Boston.h395.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "Excellent stay. The room was very clean, comfortable, and well maintained. The staff was friendly and always willing to help. The location is perfect, close to many attractions and easy access to transportation. I would definitely stay here again and highly recommend it." [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Winthrop? ### What is there to see and do in Winthrop? ### When is the best time to book a hotel with a pool in Winthrop? ## Explore a world of travel with Expedia - Lodging - Flights - Cars - Other - More ways to book - [Adults Only Resorts & in Boston ](https://www.expedia.ca/Boston-Hotels-Adults-Only-Resorts.0-0-d178239-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Business Hotels in Boston ](https://www.expedia.ca/Boston-Hotels-Business-Hotel.0-0-d178239-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Boston ](https://www.expedia.ca/Boston-Hotels-Cheap-Hotels.0-0-d178239-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Boston ](https://www.expedia.ca/Boston-Hotels-Couples-Resorts-Hotels.0-0-d178239-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Boston ](https://www.expedia.ca/Boston-Hotels-Golf-Hotel.0-0-d178239-tGolfHotel.Travel-Guide-Filter-Hotels) - 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