Title: Chestnut Hill Vacation Packages | Holiday Packages & Trips 2026/2026 from CA $664 Expedia.ca [Chestnut Hill Travel Guide](https://expedia.ca/Boston-Chestnut-Hill.dx89077)[Hotels in Chestnut Hill](https://expedia.ca/Chestnut-Hill-Boston-Hotels.0-n89077-0.Travel-Guide-Filter-Hotels)[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) ![](https://images.trvl-media.com/place/7091/40d2101a-9cd1-49a2-a1d2-7cf070ea397a.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chestnut Hill Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Ed Gaffny - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Chestnut Hill Vacation With plenty of highlights as well as hidden gems, this city is best experienced with a Chestnut Hill vacation package. Find somewhere to stay in Downtown Boston, which is great for nightlife, shopping and bars and pubs. Fill your schedule with visits to [Boston College](https://www.expedia.ca/Boston-College-Commonwealth.d6092291.Vacation-Attraction), [Paradise Rock Club](https://www.expedia.ca/Paradise-Rock-Club-Allston.d553248621533127008.Vacation-Attraction) and [Agganis Arena](https://www.expedia.ca/Agganis-Arena-Allston.d6229782.Vacation-Attraction), some of the attractions you simply have to see during your trip to Chestnut Hill. Browse Expedia's wide range of travel options and start organizing your perfect vacation to Chestnut Hill today. ## Top Holiday Package Deals in Chestnut Hill Price found within the past 48 hours. Click for updated prices. ![Boston Lodge and Suites](https://images.trvl-media.com/lodging/22000000/21340000/21333100/21333029/d2b7feac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Lodge and Suites Dorchester CA $664 per person Jan 22 - Jan 25 found 19 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 8.4/10 Very Good! (188 reviews) Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available. Reviewed on Nov 10, 2025 ![The Lenox Hotel Boston](https://images.trvl-media.com/lodging/1000000/10000/6500/6446/db068914_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Lenox Hotel Boston Back Bay CA $704 per person Feb 11 - Feb 16 found 19 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.6/10 Exceptional! (1,218 reviews) The lobby and hotel itself are beautiful, and the restaurants were fantastic. The front desk staff was also very friendly and helpful. A few areas could use some improvement: the heater in our room didn’t adjust properly and would reset itself, making the room uncomfortably warm at times. The rooms feel a bit outdated, and the toilet splashed water when flushed. Additionally, when our sheets were changed, we noticed hair left in the bed. Overall, we enjoyed our stay, but addressing these issues would make the experience even better. Reviewed on Dec 10, 2025 ![Cambria Hotel Boston Somerville](https://images.trvl-media.com/lodging/76000000/75900000/75893900/75893900/50a5a2bc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cambria Hotel Boston Somerville Spring Hill CA $915 per person Feb 9 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YYZ) to Boston (BOS) 9.6/10 Exceptional! (1,003 reviews) Absolutely beautiful hotel! My best friend and I spent a weekend in Boston Reviewed on Dec 9, 2025 ![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### citizenM Boston Back Bay Fenway–Kenmore CA $780 per person Feb 11 - Feb 16 found 19 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.4/10 Exceptional! (2,013 reviews) Great staff and nice hotel. Had a great view. Reviewed on Dec 10, 2025 ![DoubleTree Suites by Hilton Hotel Boston - Cambridge](https://images.trvl-media.com/lodging/1000000/10000/1000/946/e477f850_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree Suites by Hilton Hotel Boston - Cambridge Allston CA $724 per person Feb 11 - Feb 16 found 19 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 8.8/10 Excellent! (1,000 reviews) Everything it is a beautiful hotel!!!! Reviewed on Dec 6, 2025 ## Where to stay in Chestnut Hill Find the best Chestnut Hill areas and neighborhoods for the activities you enjoy most. [Learn more about Chestnut Hill](https://expedia.ca/Boston-Chestnut-Hill.dx89077) ![Downtown Boston showing a city and night scenes as well as a small group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/238000/238255-Downtown-Boston.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Boston 4.5/5(193 area reviews) Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here. [Find hotel + flight trips in Downtown Boston](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Boston&DestID=6340396&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Seaport District featuring a high-rise building, a river or creek and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/151000/151908-South-Boston-Waterfront.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Seaport District 1 out of top 10 points of interest in this area 4.5/5(64 area reviews) Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge. [Find hotel + flight trips in Seaport District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Seaport%20District&DestID=6146535&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Back Bay featuring a city, heritage architecture and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/151000/151657-Back-Bay.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Back Bay 1 out of top 10 points of interest in this area 4.5/5(271 area reviews) Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower. [Find hotel + flight trips in Back Bay](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Back%20Bay&DestID=800016&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Beacon Hill which includes landscape views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/21000/21013-Beacon-Hill.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Beacon Hill 1 out of top 10 points of interest in this area 5/5(1 area review) Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations. [Find hotel + flight trips in Beacon Hill](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Beacon%20Hill&DestID=77649&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/476000/476293-North-End-Boston.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### North End 1 out of top 10 points of interest in this area 4.5/5(18 area reviews) Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries. [Find hotel + flight trips in North End](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=North%20End&DestID=6146485&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Chestnut Hill Hotel Deals ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Seaport Hotel Boston 1 Seaport Lane Boston MA Fully refundableReserve now, pay when you stay CA $200 CA $240 total Dec 16 - Dec 17 includes taxes & fees 9.6/10 Exceptional! (3,766 reviews) You have to start breakfast at 6am not 7am Reviewed on Dec 5, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F12%2F2025&endDate=17%2F12%2F2025&selected=79888&PinnedHotelID=79888&HadPinnedHotel=true®ionId=89077) ![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/26d11bc3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Omni Boston Hotel at the Seaport 450 Summer Street Boston MA Fully refundableReserve now, pay when you stay CA $239 CA $335 total Dec 15 - Dec 16 includes taxes & fees 9/10 Wonderful! (4,274 reviews) Rooms were ready early Reviewed on Dec 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=15%2F12%2F2025&endDate=16%2F12%2F2025&selected=68014393&PinnedHotelID=68014393&HadPinnedHotel=true®ionId=89077) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Harborside Inn Of Boston 185 State St Boston MA CA $148 CA $173 total Dec 15 - Dec 16 includes taxes & fees 9.2/10 Wonderful! (6,023 reviews) The staff was very kind and helpful!!! Reviewed on Dec 5, 2025 [](https://expedia.ca/Hotel-Search?startDate=15%2F12%2F2025&endDate=16%2F12%2F2025&selected=202814&PinnedHotelID=202814&HadPinnedHotel=true®ionId=89077) [See all 3,762 properties in Chestnut Hill](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F12%2F2025&endDate=12%2F12%2F2025®ionId=89077) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does a Chestnut Hill vacation package cost? ### What are the cheapest months to go to Chestnut Hill? ### How many days is enough for Chestnut Hill? ### How to find the best Chestnut Hill package deals? ### Is it cheaper to book a Chestnut Hill vacation as a package? ### When to book a vacation package to Chestnut Hill? ### How to plan a trip to Chestnut Hill? > 1. Choose when to travel: Check your diary and pack your bags. Your favourite time of year and the type of activities available will also help you decide when to escape to Chestnut Hill. > 2. Set your budget: Factor in expenses such as flights, meals and transportation when working out how much to save for your trip to Chestnut Hill. Then, select a hotel that suits your budget, whether that's a wallet-friendly stay or a deluxe retreat. > 3. Decide your trip length: Think about how much time you want to spend exploring Chestnut Hill. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace. > 4. Bundle your airfare and accommodations: After you've settled on your trip dates and duration, book the right Chestnut Hill vacation package for you. ### Discover the most popular places to visit in Chestnut Hill ![Boston College](https://mediaim.expedia.com/destination/2/008a54975c35a5b86ebd267a879dd130.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston College 4/5(15 reviews) Take a campus tour or just explore the area of Boston College, during your trip to Boston. Stroll along the riverfront or attend a sporting event in this vibrant area. [](https://expedia.ca/Boston-College-Chestnut-Hill.d6092291.Vacation-Attraction) ![Fenway Park featuring a sporting event and night scenes as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/20000/20987-Fenway-Park.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Fenway Park 4.5/5(305 reviews) Catch a game or take a tour at one of America’s most historic and beloved ballparks. [](https://expedia.ca/Fenway-Park-FenwayKenmore.d6023384.Vacation-Attraction) ![Boston Common which includes flowers, a garden and landscape views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/21000/21217-Boston-Common.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston Common 4.5/5(518 reviews) The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind. [](https://expedia.ca/Boston-Common-Beacon-Hill.d507377.Vacation-Attraction) ### Things to do ![Boston CityPASS: Admission to Top 4 Boston Attractions](https://mediaim.expedia.com/localexpert/173116/5d73576c-38be-4337-8351-c85e937f9492.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston CityPASS®: Admission to Top 4 Attractions CA $111 per adult **90%** of travellers recommend [](https://expedia.ca/things-to-do/boston-citypass-admission-to-top-4-attractions.a173116.activity-details) ![Step into a festive winter oasis at Stratus bar this holiday season! Adorned with glittering icicles, sparkling lights, and festive winter elements, this experience is a must must-visit. ](https://mediaim.expedia.com/localexpert/46312679/f4dc7e7e-3f89-44f1-8c94-790c64c45eec.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### View Boston Observation Deck Admission Tickets CA $48 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/view-boston-observation-deck-admission-tickets.a46312679.activity-details) ![Go City: Boston All-Inclusive Pass with 45+ Attractions](https://mediaim.expedia.com/localexpert/173074/064eb1cc-eb4f-4535-bc3f-dbc4e50db8ab.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Go City: Boston All-Inclusive Pass with 45+ Attractions CA $118 per adult **76%** of travellers recommend [](https://expedia.ca/things-to-do/go-city-boston-all-inclusive-pass-with-45-attractions.a173074.activity-details) [See all activities in Boston](https://expedia.ca/things-to-do/search?rid=89077) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.