Title: Book the Best ROMANTIC Hotels in Winter Hill, Boston from CA $182 - Winter Hill Romantic Getaways | Expedia.ca [Winter Hill Travel Guide](https://expedia.ca/Boston-Winter-Hill.dx553248635976476697)[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)[Winter Hill Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Hill.d553248635976476697.Car-Rental-Guide)[Winter Hill Vacations](https://expedia.ca/Winter-Hill.d553248635976476697.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/romantic.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Winter Hill, Boston from CA $182 - ![](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 Winter Hill Romantic Hotels Tonight [Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976476697&startDate=2025-12-29&endDate=2025-12-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Dec 30 - Dec 31](https://www.expedia.ca/Hotel-Search?regionId=553248635976476697&startDate=2025-12-30&endDate=2025-12-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976476697&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976476697&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Winter Hill romantic hotels ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/82ab675e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/573419fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6238869c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Boston Park Plaza [](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) Bay Village 8.4/10 Very good (3112) "Great stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles CA $122 CA $198 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/dbe625a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/49683728.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, free cribs/infant beds](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/8d14bce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/e6d81cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Moxy Boston Downtown [](https://www.expedia.ca/Boston-Hotels-Moxy-Boston-Downtown.h38766175.Hotel-Information) Bay Village 8.8/10 Excellent (1009) "Great amenities and staff- perfect location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Molly CA $108 CA $182 total includes taxes & fees Jan 15 - Jan 16, 2026 [](https://www.expedia.ca/Boston-Hotels-Moxy-Boston-Downtown.h38766175.Hotel-Information) ![Suite (VIP)](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/24991d94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite | Living area](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/e4e28064.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) ![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 (1743) "Nice hotel, good location, good breakfast, and real nice friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheila CA $178 CA $255 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/60cb4bac.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/bce045e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/ce2ce7cd.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 (2356) "Nice hotel and great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James Earl CA $183 CA $261 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-The-Westin-Boston-Seaport-District.h1450057.Hotel-Information) ![Executive Suite, 1 King Bed](https://images.trvl-media.com/lodging/12000000/11270000/11264100/11264010/4f7d98c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11270000/11264100/11264010/ca1d5f7c.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) ![Mini-fridge, microwave, coffee/tea maker, cleaning supplies](https://images.trvl-media.com/lodging/12000000/11270000/11264100/11264010/2f17a542.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 (1001) "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 $146 CA $205 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Boston-Hotels-Element-Boston-Seaport-District.h11264010.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/a6dc8a96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/1ac58b6d.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/af87cf6e.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 (4351) "Staff and room was incredible Def would stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $185 CA $271 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23000/22961/56b6419d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch flat-screen TV with satellite channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/30000/23000/22961/99b05261.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) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/23000/22961/9982e9d0.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 (1713) "Clean rooms, helpful and friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammy CA $217 CA $301 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Boston-Hotels-Boston-Marriott-Copley-Place.h22961.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/45321953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/w3891h2578x6y3-d68e82bc.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) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/w3891h2595x0y0-44f52384.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 (1023) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $230 CA $330 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Boston-Hotels-InterContinental-Boston.h1573788.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/3000000/2320000/2311800/2311712/ae40a268.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2320000/2311800/2311712/c2e44637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite](https://images.trvl-media.com/lodging/3000000/2320000/2311800/2311712/6b243765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water view](https://images.trvl-media.com/lodging/3000000/2320000/2311800/2311712/c9a6a0ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Battery Wharf Hotel, Boston Waterfront [](https://www.expedia.ca/Boston-Hotels-Battery-Wharf-Hotel.h2311712.Hotel-Information) North End 8.8/10 Excellent (1751) "We stay here every visit to Boston. Pet friendly for our dogs, great location and nice accommodations and staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter CA $156 CA $237 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-Battery-Wharf-Hotel.h2311712.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22100/22046/dfa592c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/30000/22100/22046/1b7e7b0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 5:00 AM to 11:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/22100/22046/07a39e9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/1000000/30000/22100/22046/fb337f97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Boston, a Marriott Hotel [](https://www.expedia.ca/Boston-Hotels-Sheraton-Boston.h22046.Hotel-Information) Back Bay 8.6/10 Excellent (1736) "The staff and the hotel over all is excellent, can’t wait to come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Don CA $204 CA $237 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Boston-Hotels-Sheraton-Boston.h22046.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=2026-01-13&endDate=2026-01-14®ionId=553248635976476697&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Winter Hill Hotel Reviews ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "Yes" [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "The Hotel was beautiful,clean and had the perfect location but I was most impressed by the great staff. Everyone from the doorman to the cleaning ladies, the baristas, tho the front desk attendees were smiling, caring and full of joy." [](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 "Staff was very welcoming and informative about the hotel amenities. The room is quaint (in a good way) and very clean. Its not a modern hotel but its can hold its own in Boston." [](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/c414a1f3_y.jpg) ### Omni Parker House 10/10 Excellent "This was our third time staying in this hotel. This time we booked a different suite, and it was amazing. We had the best view, room service was excellent, staff was friendly. We will return. " [](https://expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a_y.jpg) ### The Langham, Boston 10/10 Excellent "Everything was so wonderful. The staff was so attentive. It was beautifully decorated. I loved the pink everywhere. The location was great to travel around the city, located in the financial district. The room was very clean and was so comfortable I never wanted to leave. I had an amazing time. I would stay there again no question. " [](https://expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information) ![The Godfrey Hotel Boston](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg) ### The Godfrey Hotel Boston 10/10 Excellent "Good service" [](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Very nice traveled with my kids, they loved it. The staff is very friendly and good." [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.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 "Very conveniently located. Best location if taking Amtrak" [](https://expedia.ca/Boston-Hotels-The-Westin-Copley-Place.h4443.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) ## Frequently asked questions ### Searching for romantic hotels in Winter Hill? ### What is there to do in Winter Hill? ### What's the best way to get to Winter Hill and around town during my romantic getaway? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [2 Star Hotels in Somerville ](https://www.expedia.ca/2Star-Somerville-Hotels.s20-0-d55192.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Somerville ](https://www.expedia.ca/3Star-Somerville-Hotels.s30-0-d55192.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Assembly Square ](https://www.expedia.ca/Assembly-Square-Boston-Hotels-All-Inclusive-Hotel.0-n553248635976007391-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - 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