Chestnut Hill Vacation Packages 2026 from $732

Chestnut Hill flight + hotel vacation packages

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

By the Sea Guests Bed & Breakfast & Suites

$732

per person

Jul 15 - Jul 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Hotel Ivy Boston Common

Bay Village

Save 100% on your flight

$964

per person

Jul 1 - Jul 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

Free WiFi in public areas, luggage storage, and a safe deposit box are available at this hotel. There's locker space and multilingual staff can provide around-the-clock assistance.

enVision Hotel Boston Everett

Save 100% on your flight

$849

per person

Jul 21 - Jul 26

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

A gym is featured at this hotel, along with self parking. WiFi in public areas is free. Traveling for business? Take advantage of the business center, express check-in, and conference center.

Nantucket Inn

Save 100% on your flight

$1,666

per person

Aug 1 - Aug 5

found 20 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

2 outdoor tennis courts, 2 hot tubs, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy a meal from the restaurant and perks like free self parking and a free beach shuttle.

Raffles Boston

Back Bay

Save 100% on your flight

$2,683

per person

Jul 1 - Jul 6

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.

Top Chestnut Hill hotels deals

Seaport Hotel Boston

1 Seaport Lane Boston MA

$202 nightly

$234 total

May 10 - May 11

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

40 Berkeley Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$157 total

May 10 - May 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

450 Summer Street Boston MA

$194 nightly

$226 total

May 10 - May 11

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

The Godfrey Hotel Boston

505 Washington Street Boston MA

$232 nightly

$270 total

May 10 - May 11

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Valet parking, a business center, and a coffee shop are also offered.

Harborside Inn Of Boston

185 State St Boston MA

$159 nightly

$185 total

May 10 - May 11

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

Omni Parker House

60 School St Boston MA

Free Cancellation

Reserve now, pay when you stay

$264 nightly

$307 total

May 10 - May 11

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, free WiFi in public areas, and valet parking. A coffee shop, express check-out, and a computer station are also on offer.

Pet friendly

Free WiFi

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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

Boston College

4.5/5(359 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.

McMullen Museum

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.

Fenway Park

4.5/5(2,543 reviews)

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

Frequently asked questions

How much are vacation packages to Chestnut Hill?

Starting at just $732, 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.