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.
Even Hotels Manchester Airport by IHG
Ocean Air Suites
Sunbird ANNEX Resort
 The Cove At Salem
Boston Harbor Hotel

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

Chestnut Hill Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
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

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
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

citizenM Boston Back Bay
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
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

Harborside Inn Of Boston
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

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.