Deals on vacations and trips to Chestnut Hill

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Chestnut Hill flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Save 100% on your flight
Price was $470, price is now $280 per person
$280
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.
The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $852, price is now $483 per person
$483
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A full-service spa, 3 restaurants, and a 24-hour gym are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, limo/town car service, and a snack bar/deli are also offered.
Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
Newton Corner
Price was $721, price is now $442 per person
$442
per person
Feb 6 - Feb 12
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and express check-out are also provided.
Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport

2.5 out of 5
Save 100% on your flight
Price was $596, price is now $377 per person
$377
per person
Jan 31 - Feb 6
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
This hotel features an indoor pool, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free buffet breakfast and a free airport shuttle. Self parking, a 24-hour business center, and free WiFi in public areas are also offered.
The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Downtown
Save 100% on your flight
Price was $686, price is now $440 per person
$440
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 4 onsite conference rooms. A snack bar/deli and concierge services are also provided.

Top Chestnut Hill hotels deals

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
$119 nightly
The price is $139 total per night
$139 total
Dec 21 - Dec 22
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A business center, express check-in, and express check-out are also on offer.
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Free Cancellation
Reserve now, pay when you stay
$216 nightly
The price is $251 total per night
$251 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
A full-service spa, 4 restaurants, and an outdoor pool are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the 24-hour gym, poolside bar, and snack bar/deli.
Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
40 Dalton St Boston MA
Free Cancellation
Reserve now, pay when you stay
$167 nightly
The price is $195 total per night
$195 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, express check-in, and express check-out are also offered.
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
70 Causeway Street Boston MA
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $125 total per night
$125 total
Dec 24 - Dec 25
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Free Cancellation
Reserve now, pay when you stay
$174 nightly
The price is $202 total per night
$202 total
Dec 17 - Dec 18
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the steam room, bar/lounge, and concierge services.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $147 total per night
$147 total
Dec 18 - Dec 19
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.
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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.

Popular places to visit

One of the prettiest & highly competitive colleges in the Boston area.

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.

Boston College
Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(2,499 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Boston Common featuring landscape views, a skyscraper and flowers

Boston Common

4.5/5(4,786 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.

Boston Common

Frequently asked questions

How much are vacation packages to Chestnut Hill?
Starting at just $280, hotel and flight packages are the perfect way to make your vacation budget stretch further. Watch out Chestnut Hill — here you come!
Where can I get the best vacation package deals for Chestnut Hill?
Look no further than Travelocity. With access to 400 airlines and a massive 1,000,000 properties across the globe, selecting the perfect Chestnut Hill package deal couldn't be easier.
Why should I book my Chestnut Hill vacation package via Travelocity?
With our Price Match Guarantee, we'll match any cheaper price you're able to find. Add on our 24/7 customer support and superb service and the vacation you've been dreaming of is well within reach.
Will I save money on my Chestnut Hill car rental if I book it with hotels and flights?
Combining your flight, hotel and car into a Chestnut Hill vacation package is a great way to score better prices. Plus, having your own set of wheels gives you total freedom to get to all those landmarks you're itching to see. Located 35 mi from Chestnut Hill, Plymouth Rock is one attraction that should be on your itinerary. Buckle up and make a day trip of it.
Which airport is best for Chestnut Hill?
Logan Intl. Airport (BOS) is popular. You'll find it approximately 8 mi northeast of Chestnut Hill. Other options worth considering are T.F. Green Airport (PVD) (45 mi away from central Chestnut Hill) and Manchester-Boston Regional Airport (MHT) (45 mi away from central Chestnut Hill).
Where should I stay when visiting Chestnut Hill?
The Trendy Chestnut Hill 1BR w/ W/D & Gym, nr Hancock Village, by Blueground is the number one choice of many visitors. Book as soon as possible before it's too late.

Photos of local treasures

Browse Chestnut Hill vacation photos for more inspiration

Photo by Ed Gaffny
Photo by Ed Gaffny
Photo by Ed Gaffny
Photo by Ed Gaffny
Photo by Yasmin
Photo by Yasmin
Photo by Yasmin
Photo by Yasmin