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 Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,656, price is now $1,192 per person
$1,192
per person
Dec 2 - Dec 6
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,476, price is now $1,298 per person
$1,298
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Save 100% on your flight
Price was $16,123, price is now $11,192 per person
$11,192
per person
Nov 23 - Nov 27
found 9 hours ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
This apartment features a gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the a rooftop terrace and perks like free self parking.
The Monty Boston

The Monty Boston

2.5 out of 5
Downtown Boston
Save 100% on your flight
Price was $3,087, price is now $2,239 per person
$2,239
per person
Dec 17 - Dec 22
found 3 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
A rooftop terrace is featured at this aparthotel, along with free WiFi in public areas and a garden. Laundry facilities and a virtual front desk are also provided.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,822, price is now $1,322 per person
$1,322
per person
Dec 2 - Dec 6
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.

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
$266 nightly
The price is $309 total per night
$309 total
Oct 30 - Oct 31
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.
Pool
Hot Tub
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Free Cancellation
Reserve now, pay when you stay
$245 nightly
The price is $284 total per night
$284 total
Oct 30 - Oct 31
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
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
$251 nightly
The price is $292 total per night
$292 total
Sep 30 - Oct 1
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
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
$248 nightly
The price is $288 total per night
$288 total
Oct 30 - Oct 31
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
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street Boston MA
Free Cancellation
Reserve now, pay when you stay
$372 nightly
The price is $433 total per night
$433 total
Oct 30 - Oct 31
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 free WiFi in public areas, express check-out, and valet parking. A coffee shop, a communal living room, and a library are also on offer.
Pet friendly
Free WiFi
Omni Parker House

Omni Parker House

4.5 out of 5
60 School St Boston MA
Free Cancellation
Reserve now, pay when you stay
$399 nightly
The price is $464 total per night
$464 total
Oct 30 - Oct 31
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, free WiFi in public areas, and valet parking. A coffee shop, express check-out, and a computer station are also on offer.
Pet friendly
Free WiFi
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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 $1,192, 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.