Title: Book the Best Hotels with POOL in Highlands in 2026 | Expedia.ca [Vacation Rentals in Boston](https://expedia.ca/Boston-Vacation-Rentals.d178239.Travel-Guide-VacationRentals)[Flights to Boston](https://expedia.ca/Cheap-Flights-To-Boston.d178239.Travel-Guide-Flights)[Things to do in Boston](https://expedia.ca/Things-To-Do-In-Boston.d178239.Travel-Guide-Activities)[Highlands Car Rentals](https://expedia.ca/Car-Rentals-In-Highlands.d553248635976468896.Car-Rental-Guide)[Highlands Vacations](https://expedia.ca/Highlands.d553248635976468896.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Highlands, MA from CA $143 - ![](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 Highlands Hotels with a Pool Tonight [Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976468896&startDate=2025-12-16&endDate=2025-12-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976468896&startDate=2025-12-17&endDate=2025-12-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976468896&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976468896&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Highlands hotels with a pool ![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) ![Presidential Suite](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/866dc285.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/1db57cc3.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 (1715) "Amazing room, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan CA $173 CA $250 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.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) ![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) ![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) ![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) ### Renaissance® Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-Renaissance-Boston-Waterfront-Hotel.h1778190.Hotel-Information) Seaport District 9.0/10 Wonderful (1004) "The room is so clean the hotel is beautiful the restaurant is amazing the service amazing to I recommend 😍" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marilyn CA $164 CA $247 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Boston-Hotels-Renaissance-Boston-Waterfront-Hotel.h1778190.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/b920b61e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/73cb3288.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 (2325) "Nice hotel and great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James Earl CA $156 CA $229 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Boston-Hotels-The-Westin-Boston-Seaport-District.h1450057.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) ![Meeting facility](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/a95c70b8.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) ![Property amenity](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/116c5658.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 (1381) "Room was nice and clean reception staff was very friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ede CA $142 CA $205 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Boston-Hotels-Aloft-Boston-Seaport-District.h11263952.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/1000000/480000/470900/470888/080f1e19.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/1000000/480000/470900/470888/fed0bbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/470900/470888/f8c0ae04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/480000/470900/470888/456b97a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Boston - Downtown [](https://www.expedia.ca/Boston-Hotels-DoubleTree-By-Hilton-Boston-Downtown.h470888.Hotel-Information) Bay Village 8.8/10 Excellent (1009) "Clean very nice room amd great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $123 CA $143 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-DoubleTree-By-Hilton-Boston-Downtown.h470888.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/12000000/11270000/11264100/11264010/cdc6335b.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) ### 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 (1002) "Room was clean and comfortable. Staff was friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $136 CA $193 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Boston-Hotels-Element-Boston-Seaport-District.h11264010.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) ![Lobby](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/4f4d7c0b.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) ![Premium Room, 1 King Bed with Sofa bed (Water View)](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/407ab4b8.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 (2709) "Good room, fantastic breakfast all very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andres CA $174 CA $202 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Seaport.h55421972.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/4c3ba16d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/19e1dda8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/22e761d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Corner (View) | Water view](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/4175b463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### InterContinental Boston by IHG [](https://www.expedia.ca/Boston-Hotels-InterContinental-Boston.h1573788.Hotel-Information) Downtown Boston 9.4/10 Exceptional (1011) "Room was clean, loved the pool, and the food was delicious! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather CA $236 CA $338 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Boston-Hotels-InterContinental-Boston.h1573788.Hotel-Information) ![Indoor pool, open 6:00 AM to 11:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/23000/22961/a9566701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Suite, 1 King Bed with Sofa bed | Living room](https://images.trvl-media.com/lodging/1000000/30000/23000/22961/20dfdeb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/30000/23000/22961/9eb1b062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23000/22961/56b6419d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boston Marriott Copley Place [](https://www.expedia.ca/Boston-Hotels-Boston-Marriott-Copley-Place.h22961.Hotel-Information) Back Bay 9.2/10 Wonderful (1712) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Farhad CA $219 CA $303 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Boston-Hotels-Boston-Marriott-Copley-Place.h22961.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/e07ab872.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/dea35c86.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) ### Seaport Hotel Boston [](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) Seaport District 9.6/10 Exceptional (3817) "Great weekend stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $233 CA $278 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.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=2025-12-30&endDate=2025-12-31®ionId=553248635976468896&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Highlands Hotel Reviews ![Hyatt Regency Boston](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/24991d94_y.jpg) ### Hyatt Regency Boston 10/10 Excellent "Excellent spa" [](https://expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.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 "The hotel is undergoing renovations which will be an exciting improvement. Still a great staff and excellent location. Will return! " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Back-Bay.h5928.Hotel-Information) ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg) ### Boston Harbor Hotel 10/10 Excellent "Yes" [](https://expedia.ca/Boston-Hotels-Boston-Harbor-Hotel.h26146.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 "It’s very convenient when you have an early flight in the am. " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.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 "The staff was very friendly and helpful. There is a restaurant connected to the hotel. Food and staff there were excellent " [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "As expected" [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "We intentionally stay at the Dagny Boston for so many reasons, but top of my list is the absolutely delightful friendliness we experience with EVERYONE on staff at the hotel. From being greeted at the door in arrival to the smiles from housekeeping staff, everyone is WONDERFUL!!! Thank you so much for a fabulous stay!!!!" [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Copley Square Hotel, a FOUND Hotel](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/72cd2881_y.jpg) ### Copley Square Hotel, a FOUND Hotel 10/10 Excellent "The staff were really friendly and accommodating. The valet was professional and right there when we needed them. The two gentlemen that checked us in at 3 PM were extremely hospitable and one of them even asked me to consider that I am in a home away from home. It was a birthday overnight with dinner and a show and we were in from out of town and already starting to have a good time so it was very nice to know that we could feel comfortable and relaxed. The overnight young woman at the front desk was also extremely hospitable and courteous as we returned from a fun night. She was very professional and patient with us when we returned and handled us with class. The rooms we stayed in were perfect for an overnight trip to Boston and Copley Square is right in the heart of Back Bay so it was perfect. Our only feedback was none of us could actually turn the heat down in the rooms. We all adjusted our thermostats to below 70 but the temperature stayed at around 72° all night. Not sure if they were overridden at the front desk, but none of the thermostats were adjusting to the temperatures that we set. That’s a little too stuffy for all of us. The outside temperature wasn’t that bad either, I believe it was in the 40s, it wasn’t freezing so we all thought that was just too warm and stuffy for sleeping. Fortunately, I was the only one who didn’t get much sleep. All of my friends were tired enough to get some sleep in their rooms before check out. Will book again w/temp control. " [](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a_y.jpg) ### The Langham, Boston 10/10 Excellent "Lovely hotel, clean room, incredibly comfortable bed, great breakfast, kind staff. That's all I ask for. " [](https://expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Highlands? ### What is there to see and do in Highlands? ### When is the best time to book a hotel with a pool in Highlands? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Cheap Hotels in Auburndale ](https://www.expedia.ca/Auburndale-Boston-Hotels-Cheap-Hotels.0-n75534-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Auburndale ](https://www.expedia.ca/Auburndale-Boston-Hotels-Hotels-With-Hot-Tubs.0-n75534-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Spa Hotels in Auburndale ](https://www.expedia.ca/Auburndale-Boston-Hotels-Spa-Hotel.0-n75534-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Banks Square Hotels ](https://www.expedia.ca/Banks-Square-Boston-Hotels.0-n553248635976474865-0.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Boston ](https://www.expedia.ca/Boston-Hotels-Adults-Only-Resorts.0-0-d178239-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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