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 $1,197, price is now $559 per person
$559
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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.
Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Price was $2,845, price is now $1,435 per person
$1,435
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,609, price is now $922 per person
$922
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Austin (AUS) 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 Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,589, price is now $1,029 per person
$1,029
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Austin (AUS) to Boston (BOS)
A restaurant and a bar/lounge are featured at this hotel. A terrace, limo/town car service, and a snack bar/deli are also on offer.
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,449, price is now $969 per person
$969
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the onsite laundry facilities and babysitting. Enjoy the sauna and perks like free WiFi.

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
$226 nightly
The price is $262 total per night
$262 total
Sep 20 - Sep 21
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
Free Cancellation
Reserve now, pay when you stay
$183 nightly
The price is $213 total per night
$213 total
Sep 10 - Sep 11
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
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
$306 nightly
The price is $357 total per night
$357 total
Sep 6 - Sep 7
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
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Free Cancellation
Reserve now, pay when you stay
$286 nightly
The price is $320 total per night
$320 total
Sep 21 - Sep 22
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
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street Boston MA
Free Cancellation
Reserve now, pay when you stay
$289 nightly
The price is $337 total per night
$337 total
Sep 13 - Sep 14
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
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
$219 nightly
The price is $255 total per night
$255 total
Sep 7 - Sep 8
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 $559, 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.