Title: 5 Stars Hotels in Chestnut Hill, Boston from CA $163 - Find Cheap Chestnut Hill Hotels With 5 Stars | Expedia.ca [Chestnut Hill Travel Guide](https://expedia.ca/Boston-Chestnut-Hill.dx89077)[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)[Chestnut Hill Car Rentals](https://expedia.ca/Car-Rentals-In-Chestnut-Hill.d89077.Car-Rental-Guide)[Chestnut Hill Vacations](https://expedia.ca/Chestnut-Hill.d89077.Destination-Travel-Guides) ![Boston_BostonCollege_6092291_05](https://images.trvl-media.com/place/6092291/d3fbc729-8f9a-4a76-9ed2-58c8f6aeade9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Chestnut Hill, Boston from CA $163 - ![](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 Chestnut Hill 5 Star Hotels Tonight [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=89077&startDate=2025-12-21&endDate=2025-12-22&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=89077&startDate=2025-12-22&endDate=2025-12-23&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=89077&startDate=2025-12-26&endDate=2025-12-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=89077&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestnut Hill 5-star hotels ![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) ![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) ![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) ### 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 (4309) "Awesome stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Xavier CA $192 CA $280 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![Apartment, 2 Bedrooms](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms | View from room](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/52ada494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/a1d3b824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Suite | Living area](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/b5cef0ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Encore Boston Harbor [](https://www.expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) Everett 9.6/10 Exceptional (3466) "Wonderful stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hosni CA $304 CA $340 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![Breakfast, lunch, brunch served; Italian cuisine ](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/54f3deb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/0910a593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/d172055e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/59caa70d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Langham, Boston [](https://www.expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information) Downtown Boston 9.6/10 Exceptional (1000) "Great location and very clean. Friendly staff and overall a wonderful stay in Boston. We would absolutely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy CA $545 CA $635 total includes taxes & fees Jan 18 - Jan 19, 2026 [](https://www.expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/400/395/130d2d37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/10000/400/395/cb7f3c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/400/395/776515ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Corner (House)](https://images.trvl-media.com/lodging/1000000/10000/400/395/df53de2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Newbury Boston [](https://www.expedia.ca/Boston-Hotels-The-Newbury-Boston.h395.Hotel-Information) Back Bay 9.2/10 Wonderful (550) "Excellent hotel. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Anne CA $502 CA $657 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Boston-Hotels-The-Newbury-Boston.h395.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/22000/21962/0d2623c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/30000/22000/21962/c3aeda44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/22000/21962/e0a50e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/22000/21962/8397fde2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Hotel Boston [](https://www.expedia.ca/Boston-Hotels-Four-Seasons-Hotel-Boston.h21962.Hotel-Information) Bay Village 9.4/10 Exceptional (454) "Very classic hotel and nice food in the restaurant " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) JUNMEI CA $994 CA $1,157 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-Four-Seasons-Hotel-Boston.h21962.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/19e1dda8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/4157cb66.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) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/22e761d4.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 (1008) "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 $227 CA $327 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Boston-Hotels-InterContinental-Boston.h1573788.Hotel-Information) ![Suite, Multiple Beds (John Adams Presidential Suite)](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Admirals Suite)](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/77e4a184.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Accessible | View from room](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/5b28f938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/ec21d2cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boston Harbor Hotel [](https://www.expedia.ca/Boston-Hotels-Boston-Harbor-Hotel.h26146.Hotel-Information) North End 9.8/10 Exceptional (1004) "Love this hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alisha CA $601 CA $701 total includes taxes & fees Jan 16 - Jan 17, 2026 [](https://www.expedia.ca/Boston-Hotels-Boston-Harbor-Hotel.h26146.Hotel-Information) ![Breakfast, lunch, dinner served; local and international cuisine ](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/b020b277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Royal Suite, 1 King Bed | View from room](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/24a77b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/52c74c33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; local and international cuisine ](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/w1667h2500x0y0-6219c43c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mandarin Oriental, Boston [](https://www.expedia.ca/Boston-Hotels-Mandarin-Oriental-Boston.h2175117.Hotel-Information) Back Bay 9.4/10 Exceptional (385) "Excellent service" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Narek CA $657 CA $765 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Boston-Hotels-Mandarin-Oriental-Boston.h2175117.Hotel-Information) ![Indoor pool, open 6:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/34000000/33470000/33464300/33464201/a484cf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Designer toiletries, hair dryer, bathrobes, slippers](https://images.trvl-media.com/lodging/34000000/33470000/33464300/33464201/f0d255cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/34000000/33470000/33464300/33464201/0fadfa3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/34000000/33470000/33464300/33464201/26f4ffb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Hotel One Dalton Street, Boston [](https://www.expedia.ca/Boston-Hotels-Four-Seasons-Hotel-One-Dalton-Street.h33464201.Hotel-Information) Back Bay 9.6/10 Exceptional (373) "Great place too stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) brian CA $732 CA $852 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Boston-Hotels-Four-Seasons-Hotel-One-Dalton-Street.h33464201.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1690000/1680100/1680030/a800c3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1690000/1680100/1680030/b78fdd6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1690000/1680100/1680030/b81f4996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/2000000/1690000/1680100/1680030/d40727de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Liberty, a Marriott Luxury Collection Hotel, Boston [](https://www.expedia.ca/Boston-Hotels-The-Liberty.h1680030.Hotel-Information) West End 8.8/10 Excellent (1009) "The restaurants and bars were really nice. The room was OK for the price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrice CA $247 CA $328 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Boston-Hotels-The-Liberty.h1680030.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/700000/696000/695991/7e37dec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/700000/696000/695991/f02e9ee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 Bedroom (Scenic Park & Boston Common View)](https://images.trvl-media.com/lodging/1000000/700000/696000/695991/94d95f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/700000/696000/695991/54668a9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, Boston [](https://www.expedia.ca/Boston-Hotels-The-Ritz-Carlton.h695991.Hotel-Information) Downtown Boston 9.0/10 Wonderful (418) "Exceptional staff, clean and well appointed room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JOHN CA $689 CA $802 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Boston-Hotels-The-Ritz-Carlton.h695991.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/f081d391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Portuguese cuisine](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/f4676063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/8bef1b8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/e8a467c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Raffles Boston [](https://www.expedia.ca/Boston-Hotels-Boston-Common-Hotel.h911477.Hotel-Information) Back Bay 9.6/10 Exceptional (202) "Loved everything about our stay, food, pool and ambiance all incredible. Will stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Don CA $718 CA $836 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-Boston-Common-Hotel.h911477.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/201200/201184/0637e89e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/210000/201200/201184/f3611f85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/210000/201200/201184/f13a1992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/210000/201200/201184/24203421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### XV Beacon [](https://www.expedia.ca/Boston-Hotels-Fifteen-Beacon.h201184.Hotel-Information) Beacon Hill 9.4/10 Exceptional (384) "I had a wonderful experience at the XV Beacon Hotel. The room and bathroom was modern and updated. I also thought the gym was clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jana CA $657 CA $765 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Boston-Hotels-Fifteen-Beacon.h201184.Hotel-Information) ![Honeymoon Room | In-room dining](https://images.trvl-media.com/lodging/97000000/96510000/96507200/96507199/39751e7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96510000/96507200/96507199/8d3d7c75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Room | Living area](https://images.trvl-media.com/lodging/97000000/96510000/96507200/96507199/c30ee3bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Room](https://images.trvl-media.com/lodging/97000000/96510000/96507200/96507199/4634641c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bell Inn [](https://www.expedia.ca/Boston-Hotels-The-Bell-Inn.h96507199.Hotel-Information) Peabody 9.4/10 Exceptional (228) "Terrific food in the Tavern! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashleigh [](https://www.expedia.ca/Boston-Hotels-The-Bell-Inn.h96507199.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Chestnut-Hill-Boston-Hotels.s50-n89077-0.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Chestnut-Hill-Boston-Hotels.s50-n89077-0.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Chestnut Hill. ![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hilton Boston Logan Airport One Hotel Drive Boston MA CA $225 CA $262 total Jan 10 - Jan 11, 2026 includes taxes & fees 8.8/10 Excellent! (3,611 reviews) [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![citizenM Boston North Station](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### citizenM Boston North Station 70 Causeway Street Boston MA CA $140 CA $163 total Dec 25 - Dec 26 includes taxes & fees 9.2/10 Wonderful! (4,180 reviews) [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Dagny Boston 89 Broad Street Boston MA CA $181 CA $259 total Jan 15 - Jan 16, 2026 includes taxes & fees 9.4/10 Exceptional! (6,845 reviews) [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) Still don't see what you're looking for? [See all properties in Chestnut Hill.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=89077&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=89077&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=89077&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=89077&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=89077&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=89077&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Chestnut Hill Stroll along the charming streets lined with historic homes and boutique shops in this affluent Boston suburb. Catch a game at Boston College's Alumni Stadium or explore the lush trails of the nearby Hammond Pond Reservation. [See all hotels in Chestnut Hill](https://www.expedia.ca/Hotel-Search?startDate=2026-01-04&endDate=2026-01-05&adults=2®ionId=89077) ![Boston_BostonCollege_6092291_05](https://images.trvl-media.com/place/6092291/d3fbc729-8f9a-4a76-9ed2-58c8f6aeade9.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high) ## Top Chestnut Hill Hotel Reviews ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg) ### Boston Harbor Hotel 10/10 Excellent "Everything was wonderful including a delicious breakfast. We will definitely return." [](https://expedia.ca/Boston-Hotels-Boston-Harbor-Hotel.h26146.Hotel-Information) ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "Egg and sausge sandwich at dunkun donuts." [](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a_y.jpg) ### The Langham, Boston 10/10 Excellent "Great location and very clean. Friendly staff and overall a wonderful stay in Boston. We would absolutely stay here again." [](https://expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information) ![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/26d11bc3_y.jpg) ### Omni Boston Hotel at the Seaport 10/10 Excellent "Smooth check in" [](https://expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![The Newbury Boston](https://images.trvl-media.com/lodging/1000000/10000/400/395/de8ba46e_y.jpg) ### The Newbury Boston 10/10 Excellent "Room was so comfortable and well appointed." [](https://expedia.ca/Boston-Hotels-The-Newbury-Boston.h395.Hotel-Information) ## Find out more about Chestnut Hill ## Five Star Hotels in Chestnut Hill There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Chestnut Hill so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Chestnut Hill and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Chestnut Hill Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Chestnut Hill The results are in, and Chestnut Hill 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Chestnut Hill! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Chestnut Hill today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### What are the best 5-star hotels in Chestnut Hill? ### How much does it cost to stay in a 5-star hotel in Chestnut Hill? > - Search for the lowest price per night from CA $163 ### What makes a hotel 5 stars in Chestnut Hill? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [1 Star Hotels in Boston ](https://www.expedia.ca/1Star-Boston-Hotels.s10-0-d178239.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Hyde Square ](https://www.expedia.ca/1Star-Hyde-Square-Boston-Hotels.s10-n553248635976474039-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Milton ](https://www.expedia.ca/1Star-Milton-Hotels.s10-0-d8635.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Allston ](https://www.expedia.ca/2Star-Allston-Boston-Hotels.s20-n73196-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Boston ](https://www.expedia.ca/2Star-Boston-Hotels.s20-0-d178239.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Somerville ](https://www.expedia.ca/2Star-Somerville-Hotels.s20-0-d55192.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Back Bay ](https://www.expedia.ca/3Star-Back-Bay-Boston-Hotels.s30-n800016-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Boston ](https://www.expedia.ca/3Star-Boston-Hotels.s30-0-d178239.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Dorchester ](https://www.expedia.ca/3Star-Dorchester-Boston-Hotels.s30-n97469-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Downtown Boston ](https://www.expedia.ca/3Star-Downtown-Boston-Boston-Hotels.s30-n6340396-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Seaport District ](https://www.expedia.ca/3Star-Seaport-District-Boston-Hotels.s30-n6146535-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Somerville ](https://www.expedia.ca/3Star-Somerville-Hotels.s30-0-d55192.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Washington Park ](https://www.expedia.ca/3Star-Washington-Park-Boston-Hotels.s30-n553248635976475959-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Wellesley ](https://www.expedia.ca/3Star-Wellesley-Hotels.s30-0-d7665.Travel-Guide-Filter-Hotels) - [3 Star Hotels in West Fens ](https://www.expedia.ca/3Star-West-Fens-Boston-Hotels.s30-n553248635976480098-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Back Bay ](https://www.expedia.ca/4Star-Back-Bay-Boston-Hotels.s40-n800016-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Boston ](https://www.expedia.ca/4Star-Boston-Hotels.s40-0-d178239.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Brookline ](https://www.expedia.ca/4Star-Brookline-Hotels.s40-0-d7091.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Cambridge ](https://www.expedia.ca/4Star-Cambridge-Hotels.s40-0-d8093.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Downtown Boston ](https://www.expedia.ca/4Star-Downtown-Boston-Boston-Hotels.s40-n6340396-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Koreatown ](https://www.expedia.ca/4Star-Koreatown-Boston-Hotels.s40-n719831526209236992-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Newton Upper Falls ](https://www.expedia.ca/4Star-Newton-Upper-Falls-Boston-Hotels.s40-n138330-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Norwood ](https://www.expedia.ca/4Star-Norwood-Hotels.s40-0-d9266.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Theatre District ](https://www.expedia.ca/4Star-Theatre-District-Boston-Hotels.s40-n800017-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Back Bay ](https://www.expedia.ca/5Star-Back-Bay-Boston-Hotels.s50-n800016-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Boston ](https://www.expedia.ca/5Star-Boston-Hotels.s50-0-d178239.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Burlington ](https://www.expedia.ca/5Star-Burlington-Hotels.s50-0-d6306.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Cambridge ](https://www.expedia.ca/5Star-Cambridge-Hotels.s50-0-d8093.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Downtown Boston ](https://www.expedia.ca/5Star-Downtown-Boston-Boston-Hotels.s50-n6340396-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Seaport District ](https://www.expedia.ca/5Star-Seaport-District-Boston-Hotels.s50-n6146535-0.Travel-Guide-Filter-Hotels) - [Hotels near Alumni Stadium ](https://www.expedia.ca/Alumni-Stadium-Hotels.0-l6228861-0.Travel-Guide-Filter-Hotels) - [Hotels near Boston College ](https://www.expedia.ca/Boston-College-Hotels.0-l6092291-0.Travel-Guide-Filter-Hotels) - [Hotels near Boston College Station ](https://www.expedia.ca/Boston-College-Station-Hotels.d6210547.Travel-Guide-Hotels) - [Inns in Boston College Station ](https://www.expedia.ca/Boston-College-Station-Inns.d6210547-aaInns.Travel-Guide-Accommodation) - [Boston Hotels ](https://www.expedia.ca/Boston-Hotels.d178239.Travel-Guide-Hotels) - [Boutique Hotels in Brighton ](https://www.expedia.ca/Brighton-Boston-Hotels-Boutique-Hotel.0-n553248635074843424-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Brighton ](https://www.expedia.ca/Brighton-Boston-Hotels-Cheap-Hotels.0-n553248635074843424-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Brighton ](https://www.expedia.ca/Brighton-Boston-Hotels-Honeymoon-Hotels.0-n553248635074843424-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Brighton ](https://www.expedia.ca/Brighton-Boston-Hotels-Hotels-With-Free-Parking.0-n553248635074843424-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Brighton ](https://www.expedia.ca/Brighton-Boston-Hotels-Luxury-Hotel.0-n553248635074843424-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Brighton ](https://www.expedia.ca/Brighton-Boston-Hotels-Oceanfront-Hotels.0-n553248635074843424-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Brighton ](https://www.expedia.ca/Brighton-Boston-Hotels-Shopping-Hotel.0-n553248635074843424-0-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Brighton ](https://www.expedia.ca/Brighton-Boston-Hotels-Spa-Hotel.0-n553248635074843424-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Brighton Hotels ](https://www.expedia.ca/Brighton-Boston-Hotels.0-n553248635074843424-0.Travel-Guide-Filter-Hotels) - [Brook Farm Hotels ](https://www.expedia.ca/Brook-Farm-Boston-Hotels.0-n553248635976475129-0.Travel-Guide-Filter-Hotels) - [Hostels in Brookline Hills Station ](https://www.expedia.ca/Brookline-Hills-Station-Hostels.d6210500-aaHostels.Travel-Guide-Accommodation) - [Hotels near Brookline Hills Station ](https://www.expedia.ca/Brookline-Hills-Station-Hotels.d6210500.Travel-Guide-Hotels) - [B&B in Chestnut Hill Station ](https://www.expedia.ca/Chestnut-Hill-Station-Bed-And-Breakfast.d6210542-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Chestnut Hill Station ](https://www.expedia.ca/Chestnut-Hill-Station-Hotels.d6210542.Travel-Guide-Hotels) - [All Inclusive Resorts and in Cleveland Circle ](https://www.expedia.ca/Cleveland-Circle-Boston-Hotels-All-Inclusive-Hotel.0-n6160076-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Cleveland Circle ](https://www.expedia.ca/Cleveland-Circle-Boston-Hotels-Beach-Hotel.0-n6160076-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Cleveland Circle ](https://www.expedia.ca/Cleveland-Circle-Boston-Hotels-Boutique-Hotel.0-n6160076-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Cleveland Circle ](https://www.expedia.ca/Cleveland-Circle-Boston-Hotels-Business-Hotel.0-n6160076-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Cleveland Circle ](https://www.expedia.ca/Cleveland-Circle-Boston-Hotels-Cheap-Hotels.0-n6160076-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Cleveland Circle ](https://www.expedia.ca/Cleveland-Circle-Boston-Hotels-Couples-Resorts-Hotels.0-n6160076-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Cleveland Circle ](https://www.expedia.ca/Cleveland-Circle-Boston-Hotels-Hotels-With-Balconies.0-n6160076-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in Cleveland Circle ](https://www.expedia.ca/Cleveland-Circle-Boston-Hotels-Hotels-With-Free-Airport-Shuttle.0-n6160076-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Cleveland Circle ](https://www.expedia.ca/Cleveland-Circle-Boston-Hotels-Hotels-With-Free-Parking.0-n6160076-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Cleveland Circle ](https://www.expedia.ca/Cleveland-Circle-Boston-Hotels-LGBT-Friendly-Hotel.0-n6160076-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Winery Hotels in Cleveland Circle ](https://www.expedia.ca/Cleveland-Circle-Boston-Hotels-Winery-Hotel.0-n6160076-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Cleveland Circle Hotels ](https://www.expedia.ca/Cleveland-Circle-Boston-Hotels.0-n6160076-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Commonwealth ](https://www.expedia.ca/Commonwealth-Boston-Hotels-Cheap-Hotels.0-n553248635976470897-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Commonwealth ](https://www.expedia.ca/Commonwealth-Boston-Hotels-Hotel-With-Pool.0-n553248635976470897-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Wifi in Commonwealth ](https://www.expedia.ca/Commonwealth-Boston-Hotels-Hotel-With-Wifi.0-n553248635976470897-0-tHotelwithwifi.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Commonwealth ](https://www.expedia.ca/Commonwealth-Boston-Hotels-Luxury-Hotel.0-n553248635976470897-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Commonwealth ](https://www.expedia.ca/Commonwealth-Boston-Hotels-Pet-Friendly-Hotel.0-n553248635976470897-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Commonwealth ](https://www.expedia.ca/Commonwealth-Boston-Hotels-Romantic-Hotel.0-n553248635976470897-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Commonwealth ](https://www.expedia.ca/Commonwealth-Boston-Hotels-Ski-Hotel.0-n553248635976470897-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Commonwealth ](https://www.expedia.ca/Commonwealth-Boston-Hotels-Spa-Hotel.0-n553248635976470897-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Commonwealth Hotels ](https://www.expedia.ca/Commonwealth-Boston-Hotels.0-n553248635976470897-0.Travel-Guide-Filter-Hotels) - [Downtown Boston Hotels ](https://www.expedia.ca/Downtown-Boston-Boston-Hotels.0-n6340396-0.Travel-Guide-Filter-Hotels) - [Hotels near Fenway Park ](https://www.expedia.ca/Fenway-Park-Hotels.0-l6023384-0.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Newton Center ](https://www.expedia.ca/Newton-Center-Boston-Hotels-Boutique-Hotel.0-n6262873-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Newton Center ](https://www.expedia.ca/Newton-Center-Boston-Hotels-Business-Hotel.0-n6262873-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Newton Center ](https://www.expedia.ca/Newton-Center-Boston-Hotels-Cheap-Hotels.0-n6262873-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Newton Center ](https://www.expedia.ca/Newton-Center-Boston-Hotels-Couples-Resorts-Hotels.0-n6262873-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Newton Center ](https://www.expedia.ca/Newton-Center-Boston-Hotels-Luxury-Hotel.0-n6262873-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Newton Center ](https://www.expedia.ca/Newton-Center-Boston-Hotels-Romantic-Hotel.0-n6262873-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Newton Center ](https://www.expedia.ca/Newton-Center-Boston-Hotels-Ski-Hotel.0-n6262873-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Newton Center Hotels ](https://www.expedia.ca/Newton-Center-Boston-Hotels.0-n6262873-0.Travel-Guide-Filter-Hotels) - [B&B in Newton Centre Station ](https://www.expedia.ca/Newton-Centre-Station-Bed-And-Breakfast.d6210485-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Rentals in Newton Centre Station ](https://www.expedia.ca/Newton-Centre-Station-Condos.d6210485-aaCondos.Travel-Guide-Accommodation) - [Hotels near Newton Centre Station ](https://www.expedia.ca/Newton-Centre-Station-Hotels.d6210485.Travel-Guide-Hotels) - [Lodges in Newton Centre Station ](https://www.expedia.ca/Newton-Centre-Station-Lodges.d6210485-aaLodges.Travel-Guide-Accommodation) - [Townhomes in Newton Centre Station ](https://www.expedia.ca/Newton-Centre-Station-Townhomes.d6210485-aaTownhomes.Travel-Guide-Accommodation) - [Spa Hotels in South Brookline ](https://www.expedia.ca/South-Brookline-Boston-Hotels-Spa-Hotel.0-n553248635976475025-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [South Brookline Hotels ](https://www.expedia.ca/South-Brookline-Boston-Hotels.0-n553248635976475025-0.Travel-Guide-Filter-Hotels) - [Hotels near South St. Station ](https://www.expedia.ca/South-St-Station-Hotels.d6210452.Travel-Guide-Hotels) - [Hotels with Balconies in St. Elizabeth's ](https://www.expedia.ca/St-Elizabeths-Boston-Hotels-Hotels-With-Balconies.0-n553248635976470180-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Romantic Hotels in St. Elizabeth's ](https://www.expedia.ca/St-Elizabeths-Boston-Hotels-Romantic-Hotel.0-n553248635976470180-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Hotels near Washington St. Station ](https://www.expedia.ca/Washington-St-Station-Hotels.d6210434.Travel-Guide-Hotels) - [Cheap Hotels in Woodland Heath ](https://www.expedia.ca/Woodland-Heath-Boston-Hotels-Cheap-Hotels.0-n553248635976472088-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Woodland Heath Hotels ](https://www.expedia.ca/Woodland-Heath-Boston-Hotels.0-n553248635976472088-0.Travel-Guide-Filter-Hotels) - [Flights to Boston ](https://www.expedia.ca/Cheap-Flights-To-Boston.d178239.Travel-Guide-Flights) - [Flights from Toronto (YYZ) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yyz/bos/toronto-to-boston) - [Visit Brighton ](https://www.expedia.ca/Boston-Brighton.dx553248635074843424) - [Boston College ](https://www.expedia.ca/Boston-College-Commonwealth.d6092291.Vacation-Attraction) - [Visit Commonwealth ](https://www.expedia.ca/Boston-Commonwealth.dx553248635976470897) - [Visit Newton Center ](https://www.expedia.ca/Boston-Newton-Center.dx6262873) - [Avis Rental Cars in Newton Center ](https://www.expedia.ca/Avis-Car-Rentals-In-Newton-Center.d6262873-c41.Car-Rental-Guide-Suppliers) - [Book Hotels in Chestnut Hill on Expedia.com ](https://www.expedia.com/5Star-Chestnut-Hill-Hotels.s50-0-d89077.Travel-Guide-Filter-Hotels)