Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Start by selecting your hotel
Start by selecting your hotel
Start by selecting your hotel

Save up to $603 by booking Flight + Hotel.

Search 590,000 properties and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

Chestnut Hill

Basing yourself in Chestnut Hill?

Packages in Chestnut Hill

Pair your flight and hotel bookings via Expedia. Our lodging and flight deals are the best way to save time and money. While you are staying in Chestnut Hill, pamper yourself with your extra cash.

Savvy voyagers can save up to $603 by securing their package deals with us.

About 400 partner airlines and 321,000 hotels worldwide are ready for you to book on our exhaustive international database.

Take a look at some of the best prices ever at Expedia and treat yourself to the trip you so badly deserve. Your family will thank you for it.

You can alter your travel bookings with us because we do not charge cancellation fees for almost all of our reservations.

Chestnut Hill Vacation Packages

From here, you can get out and explore Boston, the capital city of Massachusetts. At the moment, the city's permanent population is about 600,000. The city center is 6 miles from Chestnut Hill, while Logan International Airport is about 8 miles to the northeast of this neighborhood.

Get familiar with the area with some nearby tourist attractions, including Louisburg Square and Minuteman Bikeway. Cathedral of the Holy Cross and The Games People Play are also recommended by visitors and locals alike. Another thought is to head over to a nearby area, such as Cleveland Circle or Brookline.

Hynes Convention Center, one of the top landmarks in the country, is 4 miles to the northeast.

Black Falcon Cruise Terminal and John F. Kennedy Library and Museum are just some of the entertaining choices waiting for you in this vibrant city. If you have time, don't forget about World Trade Center and Institute of Contemporary Art.

Organize a babysitter and swing by for some fun at Samuel Adams Brewery and Beacon Trotting Park.

Like to give your brain a workout? Handel and Haydn Society and Mapparium are a few recommended cultural attractions.

Treat your eyes to the stunning works at Boston Museum of Fine Arts, Isabella Stewart Gardner Museum, Museum of the National Center of Afro American Artists and McMullen Museum. These are great places to meet fellow art lovers.

Wander around the fascinating collections and check for any guided tours at Mary Baker Eddy Library, Warren Anatomical Museum, Larz Anderson Auto Museum and Jackson Homestead and Museum.

Watch a show at Huntington Theatre, Boston Symphony Hall, New England Conservatory of Music and House of Blues Boston. You'll want to book your tickets as early as possible.

Do you think you've got the skills to bag a few birdies at William J. Devine Municipal Golf Course and George Wright Golf Club? These well-loved courses give even the best players a real run for their money.

Go outdoors and take in the clean air at one of the nature areas, such as Back Bay Fens, Charles River Bike Path and Chestnut Hill Reservoir.

Nearby urban parks include Arnold Arboretum, Boston Nature Center, The Fens and Wheeler Park. Take a stroll or read a newspaper in the shade.

Brush aside the cobwebs of the past at Christian Science Plaza, Berklee College of Music, Northeastern University and Boston University. These time-weathered sites have plenty of interesting stories to tell.

At the sporting heart of Boston is Agganis Arena, the stomping ground of the Boston University Terriers and the Boston University Terriers. This versatile stadium is also a fabulous concert venue, so be sure to browse the official website to see what's available.

Accommodation in Chestnut Hill

When a place is as popular as Chestnut Hill, it's not surprising that there's a huge range of accommodation options to choose from. You'll find 93 Chestnut Hill lodgings on Expedia's easy-to-use website.

Travelers who delight in luxury and style can choose from the Mandarin Oriental Boston, at 776 Boylston St, and the Fairmont Copley Plaza, Boston, at 138 Saint James Ave. If you're after something a bit cheaper, the Harvard Square Hotel, 110 Mount Auburn Street, or the Days Hotel-Boston/Cambridge, 1234 Soldiers Field Rd, may be more to your liking.

Top Hotel Deals

See all 1,210 Hotels in Chestnut Hill
Directly Across the Street From Boston College With Parking!
Directly Across the Street From Boston College With Parking!

Directly Across the Street From Boston College With Parking!

, Newton
    of 5, from 6 reviews
    0.0 out of 5.0

    Situated in Chestnut Hill, this property is close to Boston College, Great Scott, and Coolidge Corner Theatre. Area attractions also include Boston University and Harvard Square.

    Amazing Single House in Brookline
    Amazing Single House in Brookline

    Amazing Single House in Brookline

    230 Middlesex Road, Chestnut Hill
      4.0 out of 5.0

      This vacation home is located in Chestnut Hill (Cleveland Circle), close to Boston College, Boston University, and Dana-Farber Cancer Institute. Local attractions also include Beth Israel Deaconess Medical Center and Great Scott.

      Revere Hotel Boston Common $202
      Revere Hotel Boston Common

      Revere Hotel Boston Common

      200 Stuart St, Boston
        of 5, from 4,423 reviews
        4.0 out of 5.0

        The Revere Hotel is at the edge of the Theatre District, 1 block from the Arlington "T" Station and 2 blocks from Boston Common and the Public Garden.

        The Godfrey Hotel Boston $188
        The Godfrey Hotel Boston

        The Godfrey Hotel Boston

        505 Washington Street, Boston
          of 5, from 1,239 reviews
          4.0 out of 5.0

          Located in Downtown Boston, this boutique hotel is steps from Boston Opera House and Orpheum Theater. Boston Common and Boston Public Garden are also within 10 minutes.

          Boston Omni Parker House Hotel $169
          Boston Omni Parker House Hotel

          Boston Omni Parker House Hotel

          60 School St, Boston
            of 5, from 4,652 reviews
            4.0 out of 5.0

            Located on Freedom Trail in downtown Boston, this hotel is 3 blocks from Quincy Market, 2 from the State House and Boston Common, and adjacent to the Financial District. The hotel is 10 minutes from Logan International Airport by car and 20 minutes by train for only USD 2 each way.

            Lakeside Inn $75
            Lakeside Inn

            Lakeside Inn

            595 North Ave, Wakefield
              of 5, from 2,827 reviews
              2.0 out of 5.0

              Situated on a lake, this hotel is 3.1 mi (5 km) from Woburn Mall and within 12 mi (20 km) of Burlington Mall and Square One Mall. Royall Park and Somerville Theatre are also within 12 mi (20 km).

              Boston Park Plaza $146
              Boston Park Plaza

              Boston Park Plaza

              50 Park Plaza at Arlington Street, Boston
                of 5, from 2,382 reviews
                4.0 out of 5.0

                Located in historic Back Bay, this hotel just completed a $100 million dollar renovation, and is 3 miles from Logan International Airport and 200 yards from the Boston Common and Public Garden. The hotel is easily accessible to Newbury Street shopping.

                Sheraton Boston Hotel $129
                Sheraton Boston Hotel

                Sheraton Boston Hotel

                39 Dalton St, Boston
                  of 5, from 3,546 reviews
                  4.0 out of 5.0

                  This hotel in Boston's historic Back Bay provides indoor access to the Hynes Convention Center, the Prudential Center, Copley Place malls, numerous shops and restaurants, as well as a subway station.

                  Top Flight + Hotel Deals

                  Top Deals on Flights

                  These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.