An aerial view of a river flanked by dense forests with autumn foliage.

Chestnut Hill Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Chestnut Hill Vacation

With plenty of highlights as well as hidden gems, this city is best experienced with a Chestnut Hill vacation package. Find somewhere to stay in Downtown Boston, which is great for nightlife, shopping and bars and pubs. Fill your schedule with visits to Boston College, Paradise Rock Club and Agganis Arena, some of the attractions you simply have to see during your trip to Chestnut Hill. Browse Expedia's wide range of travel options and start organizing your perfect vacation to Chestnut Hill today.

The Latest Chestnut Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A spacious, elegantly designed dining area with high ceilings, chandeliers, and classic decor.
    Jan 31 - Feb 3

    The Langham, Boston + Flight

    Downtown Boston
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,000 reviews)
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,556
    CA $1,033
    per traveller
    found 19 hours ago
    The Langham, Boston
  • A spacious hotel lobby with a dining area, seating, large windows, and a chandelier.
    Jan 31 - Feb 3

    Boston Harbor Hotel + Flight

    North End
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    "!"
    Reviewed November 10, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $2,120
    CA $1,143
    per traveller
    found 19 hours ago
    Boston Harbor Hotel
  • A courtyard with brick walls, outdoor seating, and potted plants.
    Jan 29 - Feb 1

    Four Seasons Hotel Boston + Flight

    Bay Village
    3 nights
    5.0 star property
    9.4/10 - Exceptional (497 reviews)
    "The best location and the beat service! The best swimming pool"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $2,361
    CA $1,525
    per traveller
    found 1 day ago
    Four Seasons Hotel Boston
  • Pool
    Jan 29 - Feb 1

    Raffles Boston + Flight

    Back Bay
    3 nights
    5.0 star property
    9.6/10 - Exceptional (357 reviews)
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $2,311
    CA $1,581
    per traveller
    found 1 day ago
    Raffles Boston
  • A rooftop dining area with a round table set for two, surrounded by plush seating and potted plants.
    Jan 29 - Feb 1

    The Newbury Boston + Flight

    Back Bay
    3 nights
    5.0 star property
    9.4/10 - Exceptional (749 reviews)
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,804
    CA $1,283
    per traveller
    found 1 day ago
    The Newbury Boston

Where to stay in Chestnut Hill

Find the best Chestnut Hill areas and neighborhoods for the activities you enjoy most. Learn more about Chestnut Hill
Learn more about Chestnut Hill
Quincy Market with an American flag, historic buildings, and a clock tower in the background.

Downtown Boston

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.
A historic church with a large central tower and multiple spires, surrounded by modern buildings and a public square with people and greenery.

Back Bay

Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.
A city skyline at dusk with illuminated buildings reflecting on the water, a prominent bridge, and a large chain barrier along the waterfront.

Seaport District

Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.
A large brick building with a golden dome, a flagpole with the American flag, and a statue in front.

Beacon Hill

Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.
A statue of a man on horseback in a park with trees, a clock tower, and brick buildings in the background.

North End

Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.

Discover the most popular places to visit in Chestnut Hill

McMullen Museum

6.0/10 (1 review)
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.
See properties

What to do near Chestnut Hill

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $69
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
See all activities near Chestnut Hill

Chestnut Hill Hotel Deals

A modern living room with a fireplace, seating area, and large windows.

Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
2.5 star property
3.5 km from Chestnut Hill
9.2 out of 10, Wonderful, (1,237 reviews)
"Breakfast was lousy. Food did not taste good. Room shower sliding door wouldn't stay closed, spray handle did not work. Parking overpriced. Front desk staff very nice and professional."
The price is CA $156
CA $174 total
includes taxes & fees
Nov 22 - Nov 23
Hampton Inn & Suites Watertown Boston
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.
See all properties in Chestnut Hill

Frequently Asked Questions

How much does a Chestnut Hill vacation package cost?

You can pick up a vacation package to this top destination from CA $1,033 on Expedia. But how much your vacation to Chestnut Hill costs will depend on the length of stay, hotel choice and season.

What are the cheapest months to go to Chestnut Hill?

You can usually find lower prices and better availability in January, February and November. Browse our cheap Chestnut Hill vacation packages and you could land some excellent off-season deals.

How many days is enough for Chestnut Hill?

With about 3 days, you'll have plenty of time to visit popular neighbourhoods such as Coolidge Corner South Side and Griggs Park during your Chestnut Hill vacation. Remember to also add Frederick Law Olmsted National Historic Site and GASP to your sightseeing list. Looking for more adventures? Consider venturing outside of Chestnut Hill on day trips and tours.

How to find the best Chestnut Hill package deals?

Begin your search for a Chestnut Hill package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Chestnut Hill package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chestnut Hill escape off to a flying start.

Is it cheaper to book a Chestnut Hill vacation as a package?

An Expedia vacation package could land you considerable savings when compared to booking flights and stays individually. Better still, you can customize your Chestnut Hill trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.

When to book a vacation package to Chestnut Hill?

If you're considering a spur-of-the-moment Chestnut Hill adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.

How to plan a trip to Chestnut Hill?

  1. Choose when to travel: Check your diary and pack your bags. Your favourite time of year and the type of activities available will also help you decide when to escape to Chestnut Hill.
  2. Set your budget: Factor in expenses such as flights, meals and transportation when working out how much to save for your trip to Chestnut Hill. Then, select a hotel that suits your budget, whether that's a wallet-friendly stay or a deluxe retreat.
  3. Decide your trip length: Think about how much time you want to spend exploring Chestnut Hill. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your airfare and accommodations: After you've settled on your trip dates and duration, book the right Chestnut Hill vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.