Chestnut Hill Vacation Packages 2025/2026 from $399

Chestnut Hill flight + hotel vacation packages

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

Boston Lodge and Suites

Dorchester

$399

per person

Dec 6 - Dec 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Boston Harbor Hotel

North End

$986

per person

Dec 7 - Dec 13

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.

Raffles Boston

Back Bay

$1,311

per person

Dec 7 - Dec 13

found 1 day 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.

DoubleTree Suites by Hilton Hotel Boston - Cambridge

Allston

Save 100% on your flight

$688

per person

Nov 1 - Nov 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free train station pick-up. Enjoy the 24-hour gym and perks like a free area shuttle.

The Charles Hotel

West Cambridge

Save 100% on your flight

$927

per person

Dec 7 - Dec 13

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.

Top Chestnut Hill hotels deals

citizenM Boston North Station

70 Causeway Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$244 nightly

$284 total

Oct 5 - Oct 6

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.

Free WiFi

Restaurant

Seaport Hotel Boston

1 Seaport Lane, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$280 nightly

$325 total

Sep 28 - Sep 29

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

Omni Boston Hotel at the Seaport

450 Summer Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$294 nightly

$343 total

Oct 5 - Oct 6

Total with taxes and fees

A full-service spa, 4 restaurants, and an outdoor pool are all featured at this smoke-free 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

The Dagny Boston

89 Broad Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$339 nightly

$395 total

Oct 5 - Oct 6

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 library, and a computer station are also on offer.

Pet friendly

Free WiFi

citizenM Boston Back Bay

408 Newbury street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$244 nightly

$284 total

Oct 19 - Oct 20

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 coffee shop, a communal living room, and express check-in are also on offer.

Free WiFi

Restaurant

Hilton Boston Logan Airport

One Hotel Drive, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$303 nightly

$353 total

Sep 28 - Sep 29

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, express check-in, and free airport shuttle. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Pool

Free airport shuttle

Don't see what you're looking for?

See all available properties in Chestnut Hill

View all properties

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

Take a campus tour or just explore the area around Boston College, a top college in Boston. Stroll along the riverfront or attend a sporting event in this vibrant area.

Alumni Stadium

Catch an event at Alumni Stadium during your trip to Boston. Experience the fascinating museums and acclaimed art scene in this vibrant area.

Conte Forum

Catch an event at Conte Forum during your trip to Boston. Experience the area's art scene and live music.

Frequently asked questions

How much are vacation packages to Chestnut Hill?

Starting at just $399, 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.