Chestnut Hill Vacation Packages 2025/2026 from $497

Chestnut Hill flight + hotel vacation packages

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

Lakeside Inn

Save 100% on your flight

per person

Aug 23 - Aug 30

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Josiah Keith House

Save 100% on your flight

per person

Aug 23 - Aug 30

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

Free WiFi in public areas, a garden, and a picnic area are available at this bed & breakfast. Enjoy the free full breakfast each morning. Laundry facilities and concierge services are also provided.

DoubleTree by Hilton Boston North Shore

Save 100% on your flight

per person

Aug 23 - Aug 30

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

This hotel features 2 restaurants, an indoor pool, and a gym. Families will appreciate the arcade/game room and convenience store. Enjoy the sauna and perks like free self parking.

Sunbird ANNEX Resort

Save 100% on your flight

per person

Aug 28 - Sep 1

found 11 hours ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

This hotel features an indoor pool and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

The Windsor Inn

Central Square

Save 100% on your flight

per person

Aug 23 - Aug 30

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A terrace, a garden, and a picnic area are also on offer.

Top Chestnut Hill hotels deals

Omni Boston Hotel at the Seaport

450 Summer Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$246 nightly

$287 total

Aug 10 - Aug 11

Total includes 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.

citizenM Boston Back Bay

408 Newbury street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$184 nightly

$214 total

Jul 20 - Jul 21

Total includes 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

Harborside Inn Of Boston

185 State St, Boston, MA

$229 nightly

$267 total

Jul 20 - Jul 21

Total includes 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.

citizenM Boston North Station

80-120 Causeway Street, Boston, MA

$169 nightly

$197 total

Jul 20 - Jul 21

Total includes 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.

Copley Square Hotel, a FOUND Hotel

47 Huntington Ave, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$151 nightly

$176 total

Aug 10 - Aug 11

Total includes taxes and fees

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, express check-out, and luggage storage are also offered.

The Revolution Hotel

40 Berkeley Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$220 total

Jul 20 - Jul 21

Total includes 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.

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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.

Popular places to visit

One of the prettiest & highly competitive colleges in the Boston area.

Boston College

4.5/5(354 reviews)

Take a campus tour or just explore the area of Boston College, during your trip to 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 $497, 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.