Chestnut Hill Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Chestnut Hill
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
Price was CA $1,541, price is now CA $792 per person
CA $792
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (190 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 Langham, Boston
Downtown Boston
Price was CA $2,030, price is now CA $1,439 per person
CA $1,439
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,010 reviews)
Well located and very well maintained property.
Reviewed on Jun 11, 2026
By the Sea Guests Bed & Breakfast & Suites
Price was CA $2,048, price is now CA $1,495 per person
CA $1,495
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (188 reviews)
It’s a cute little place right on the ocean with its own beach.
Reviewed on Jun 12, 2026
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
Downtown Boston
4.5/5(197 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.
Chestnut Hill Hotel Deals
The Revolution Hotel
40 Berkeley Street Boston MA
9/10 Wonderful! (2,681 reviews)
"Nice and cozy central close to a ton of dining and shopping."
Reviewed on Jun 20, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $271 per night from Jul 2 to Jul 3
CA $271
CA $373 total
Jul 2 - Jul 3
includes taxes & fees
9.2/10 Wonderful! (4,714 reviews)
"Excellent experience all around. I would absolutely stay again."
Reviewed on Jun 19, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
9.6/10 Exceptional! (4,451 reviews)
"Perfect location. Rooms are great and clean. Staff is helpful. We stay yearly and have never had a negative interaction."
Reviewed on Jun 19, 2026
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.
Discover the most popular places to visit in Chestnut Hill
Fenway Park
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Gillette Stadium
Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's great live music and acclaimed theater scene.
Harvard University
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $73
per adult
90% of travellers recommend
View Boston Observation Deck Admission Tickets
CA $47
per adult
88% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $116
per adult
92% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.