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.
Brewster Green Resort

Brewster Green Resort

3.5 out of 5
Price was $813, price is now $608 per person
$608
per person
Jan 22 - Jan 25
found 10 hours ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
2 outdoor tennis courts, an outdoor pool, and an indoor pool are all featured at this aparthotel. Enjoy the gym and perks like free self parking and free WiFi. There's a hot tub on site, and barbecue grills and a virtual front desk are also offered.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,651, price is now $979 per person
$979
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was $1,308, price is now $974 per person
$974
per person
Jan 11 - Jan 14
found 23 hours ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.
Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

3 out of 5
North Brookline
Price was $858, price is now $648 per person
$648
per person
Dec 10 - Dec 14
found 10 hours ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
This apartment features a virtual front desk. Take advantage of the self parking.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was $1,695, price is now $1,289 per person
$1,289
per person
Jan 21 - Jan 24
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
A full-service spa, 3 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like free WiFi. You'll appreciate the a rooftop terrace, bar/lounge, and concierge services.

Top Chestnut Hill hotels deals

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
$174 nightly
The price is $203 total per night
$203 total
Nov 22 - Nov 23
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. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.
Pool
Hot Tub
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
$113 nightly
The price is $131 total per night
$131 total
Nov 23 - Nov 24
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.
Pet friendly
Free WiFi
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Free Cancellation
Reserve now, pay when you stay
$165 nightly
The price is $192 total per night
$192 total
Nov 23 - Nov 24
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.
Pool
Pet friendly
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Free Cancellation
Reserve now, pay when you stay
$162 nightly
The price is $188 total per night
$188 total
Nov 24 - Nov 25
Total with taxes and fees
This luxury hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a 24-hour business center, and a coffee shop are also offered.
Pet friendly
Free WiFi
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Free Cancellation
Reserve now, pay when you stay
$266 nightly
The price is $297 total per night
$297 total
Nov 29 - Nov 30
Total with taxes and fees
This luxury hotel features a casino, a full-service spa, and a nightclub. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Free self parking is free for guests, and you can enjoy a meal in one of the 15 restaurants.
Spa
Parking included
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
$129 nightly
The price is $150 total per night
$150 total
Nov 22 - Nov 23
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.
Free WiFi
Restaurant
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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.

Stay near popular Chestnut Hill attractions

McMullen Museum

6.0/10 (1 review)
You can study the exhibits at McMullen Museum, a museum with a storied past, during your travels to Newton. Experience the acclaimed art scene or attend a sporting event in this vibrant area.
See properties

Frequently asked questions

How much are vacation packages to Chestnut Hill?
Starting at just $608, 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

An aerial view of a river flanked by dense forests with autumn foliage.
A golf course with a clear path, trees, and a distant hill.
A library with wooden floors, multiple computer stations, and people working.
A large stone building with a clock tower and a green lawn in front.
A building with a black ornate entrance, number 172, and decorative ironwork.