Chestnut Hill Vacation Packages 2025 from $497

Chestnut Hill flight + hotel vacation packages

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

Mari-Anne Motel

Hampton Beach

Save 100% on your flight

per person

Aug 28 - Sep 1

found 4 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

Ocean Air Suites

Hampton Beach

Save 100% on your flight

per person

Aug 28 - Sep 1

found 4 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

This aparthotel includes a picnic area and barbecue grills. Take advantage of the free self parking.

Holly Tree Resort

Save 100% on your flight

per person

Jul 8 - Jul 12

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.

Sea Mist Resort

Save 100% on your flight

per person

Jul 24 - Jul 27

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

This aparthotel features an outdoor pool and an indoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and perks like free self parking.

The Cove At Salem

Save 100% on your flight

per person

Aug 14 - Aug 17

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A communal living room and barbecue grills are also provided.

Top Chestnut Hill hotels deals

YOTEL Boston

65 Seaport Blvd, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$229 nightly

$266 total

Jun 30 - Jul 1

Total includes taxes and fees

The hotel's 24-hour gym, a rooftop terrace, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Free WiFi

Restaurant

Omni Boston Hotel at the Seaport

450 Summer Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$234 nightly

$273 total

Jun 7 - Jun 8

Total includes taxes and fees

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

Spa

Four Points by Sheraton Boston Newton

320 Washington Street, Newton, MA

Free Cancellation

Reserve now, pay when you stay

$195 nightly

$217 total

Jun 20 - Jun 21

Total includes taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and a snack bar/deli are also provided.

Pool

Pet friendly

The Revolution Hotel

40 Berkeley Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$170 nightly

$198 total

Jun 30 - Jul 1

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.

Pet friendly

Free WiFi

The Dagny Boston

89 Broad Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$259 nightly

$302 total

Jun 8 - Jun 9

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 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

$179 nightly

$208 total

Jun 30 - Jul 1

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

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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

Fenway Park

4.5/5(2,499 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Harvard University

4.5/5(1,966 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Boston Common

4.5/5(4,786 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

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.