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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $928, price is now $525 per person
$525
per person
Oct 20 - Oct 22
found 24 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner
Save 100% on your flight
Price was $2,403, price is now $1,416 per person
$1,416
per person
Sep 23 - Sep 30
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Boston (BOS)
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 computer station, dry cleaning, and luggage storage are also on offer.
Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

3 out of 5
North Brookline
Save 100% on your flight
Price was $2,946, price is now $1,896 per person
$1,896
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Boston (BOS)
This apartment features a virtual front desk. Take advantage of the self parking.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Save 100% on your flight
Price was $2,044, price is now $1,368 per person
$1,368
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Express check-in, express check-out, and luggage storage are available at this hotel. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Laundry facilities and a virtual front desk are also provided.
Black Walnut Inn

Black Walnut Inn

2 out of 5
North Amherst
Save 100% on your flight
Price was $1,317, price is now $890 per person
$890
per person
Oct 22 - Oct 25
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning. A lobby fireplace, a communal living room, and express check-in are also on offer.

Top Chestnut Hill hotels deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Free Cancellation
Reserve now, pay when you stay
$219 nightly
The price is $254 total per night
$254 total
Aug 30 - Aug 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.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Free Cancellation
Reserve now, pay when you stay
$151 nightly
The price is $176 total per night
$176 total
Aug 13 - Aug 14
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.
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
$270 nightly
The price is $315 total per night
$315 total
Aug 30 - Aug 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.
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street Boston MA
Free Cancellation
Reserve now, pay when you stay
$248 nightly
The price is $289 total per night
$289 total
Aug 30 - Aug 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.
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

3 out of 5
220 Huntington Avenue Boston MA
Free Cancellation
Reserve now, pay when you stay
$189 nightly
The price is $220 total per night
$220 total
Aug 16 - Aug 17
Total with taxes and fees
A gym is featured at this hotel, along with self parking. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. There's a fireplace in the lobby and multilingual staff can provide around-the-clock assistance.
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
$199 nightly
The price is $232 total per night
$232 total
Aug 16 - Aug 17
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.
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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 $525, 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.