Chestnut Hill Vacation Packages 2025/2026 from $322

Q: 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.

Chestnut Hill flight + hotel vacation packages

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

Maverick Suites at 40 Temple St

Beacon Hill

Save 100% on your flight

$322

per person

Feb 5 - Feb 10

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

This aparthotel features laundry facilities.

Eurostars The Boxer

West End

Save 100% on your flight

$598

per person

Dec 30 - Jan 4

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Business travelers can take advantage of the business center. A computer station, dry cleaning, and luggage storage are also on offer.

The Charles Hotel

West Cambridge

Save 100% on your flight

$882

per person

Feb 12 - Feb 16

found 6 hours ago

Roundtrip flight included

Charlotte (CLT) 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.

The Hotel Portsmouth

Downtown

Save 100% on your flight

$511

per person

Dec 31 - Jan 6

found 11 hours ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 4 onsite conference rooms. A snack bar/deli and concierge services are also provided.

The Whitney Hotel

Beacon Hill

Save 100% on your flight

$949

per person

Dec 30 - Jan 4

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a garden, and a lobby fireplace are also offered.

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 of Boston College, during your trip to Boston. Stroll along the riverfront or attend a sporting event in this vibrant area.

Fenway Park

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

Boston Common

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 $322, 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.