Chestnut Hill Vacations from $343
Book a Hotel + Flight or Car together to unlock savings
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, Paradise Rock Club and Agganis Arena, 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.
The Latest Chestnut Hill Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Ocean Air Suites
Hampton Beach
Save 100% on your flight
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Boston (BOS)
9.2/10 Wonderful! (32 reviews)
location was awesome. able to see fireworks right from deck in the back. It’s definitely family friendly would definitely be coming back again next year :)
Reviewed on Sep 3, 2024
The Cove At Salem
Save 100% on your flight
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (576 reviews)
Very clean. The room is decorated in a very stylish manner that goes with the theme of the city. Located conveniently within walking distance to the city center.
Reviewed on Jul 11, 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
Downtown Boston
4.5/5(2,415 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
Omni Boston Hotel at the Seaport
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
$246 nightly
The price is $287 total per night from Aug 10 to Aug 11
$287 total
Aug 10 - Aug 11
Total includes taxes and fees
9/10 Wonderful! (3,662 reviews)
"Very nice views, clean and conveniently located."
Reviewed on Jul 11, 2025
citizenM Boston Back Bay
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $214 total per night from Jul 13 to Jul 14
$214 total
Jul 13 - Jul 14
Total includes taxes and fees
9.2/10 Wonderful! (1,404 reviews)
"Good location. Cool European concept hotel. Good food and drink options. Would stay again. No onsite parking."
Reviewed on Jul 10, 2025
Harborside Inn Of Boston
185 State St, Boston, MA
$229 nightly
The price is $267 total per night from Jul 13 to Jul 14
$267 total
Jul 13 - Jul 14
Total includes taxes and fees
9/10 Wonderful! (5,303 reviews)
"this property was perfect for our stay in Bostain. First of all the room was large, clean and very comfortable. The front desk staff was very pleasant. The best part about this hotel is the location. You are on the waterfront and within walking distance of everything you need including many tours. ..."
Reviewed on Jul 10, 2025
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
Boston College
4.5/5(354 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.
Alumni Stadium
Catch an event at Alumni Stadium during your trip to Boston. Experience the fascinating museums and acclaimed art scene in this vibrant area.
McMullen Museum
You can study the exhibits at McMullen Museum, a museum with a storied past, during your travels to Newton. Experience the fascinating museums or attend a sporting event in this vibrant area.
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
$79
per adult
90% of travellers recommend
Liberty, Freedom, and Revolution: American History Tours Bundle
$25
per traveler
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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- Alumni Stadium
- Boston College
- Cleveland Circle Vacations
- Andover Newton Theological School
- Larz Anderson Auto Museum
- Boston Museum of Fine Arts
- Boston Vacations
- Frederick Law Olmsted National Historic Site
- The Silver Woman
- Visit Cleveland Circle
- Arnold Arboretum
- St. Elizabeth's Medical Center
- Visit Newton Center
- Brookline Vacations
- Isabella Stewart Gardner Museum
- Jamaica Plain Vacations
- Brookline Farmers Market
- Coolidge Corner Theatre
- Newton Vacations
- Visit Newton Highlands
- Car rentals near Boston
- Car rental Boston Airport (BOS)
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- Car rentals near Cleveland Circle
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- Enterprise Rental Cars in Brookline
- Car rentals near St. Elizabeth's Medical Center
- Car rentals near Newton Highlands
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.