Chestnut Hill Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Ed Gaffny

  • 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.

Price found within the past 48 hours. Click for updated prices.
  • Front of property
    Jul 12 - Jul 17

    Hotel Ivy Boston Common + Flight

    Bay Village
    4 nights
    2.5 star property
    8.4/10 - Very good (1,453 reviews)
    "Safe, friendly staff, garage discount, great location. Easy check in and check out."
    Reviewed May 18, 2026
    Roundtrip • Edmonton (YEG) - Boston (BOS)
    YEG - BOS • 1 stop BOS - YEG • 1 stop
    CA $2,119
    CA $1,361
    per traveller
    found 1 day ago
    Hotel Ivy Boston Common
  • Game room
    Jul 12 - Jul 17

    Meco Hotel - Hostel + Flight

    West End
    4 nights
    2.0 star property
    8.6/10 - Excellent (422 reviews)
    "Great access very cheep. Was not expecting that much for a reasonable price, but was surprised when they had a 24h autolock, well furnished and clean bunkers, and most importantly, well mannerred room mates. Also had a small snack stand, free coffee in the morning which made me very happy. would love to stay here again! "
    Reviewed May 18, 2026
    Roundtrip • Edmonton (YEG) - Boston (BOS)
    YEG - BOS • 1 stop BOS - YEG • 1 stop
    CA $2,754
    CA $1,620
    per traveller
    found 1 day ago
    Meco Hotel - Hostel
  • Breakfast meal
    Jun 24 - Jun 30

    By the Sea Guests Bed & Breakfast & Suites + Flight

    Dennis Port
    6 nights
    3.5 star property
    9.2/10 - Wonderful (185 reviews)
    "."
    Reviewed October 16, 2025
    Roundtrip • Toronto (YTZ) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YTZ • Nonstop
    CA $2,487
    CA $1,561
    per traveller
    found 8 hours ago
    By the Sea Guests Bed & Breakfast & Suites
  • Reception
    Jul 11 - Jul 17

    The Inn at Hastings Park, Relais & Chateaux - Boston + Flight

    Lexington
    6 nights
    4.0 star property
    9.6/10 - Exceptional (256 reviews)
    "Splendid bed and breakfast"
    Reviewed April 29, 2026
    Roundtrip • Edmonton (YEG) - Boston (BOS)
    YEG - BOS • 1 stop BOS - YEG • 1 stop
    CA $3,227
    CA $2,056
    per traveller
    found 1 day ago
    The Inn at Hastings Park, Relais & Chateaux - Boston
  • Suite, Multiple Beds (John Adams Presidential Suite)
    Jul 24 - Jul 29

    Boston Harbor Hotel + Flight

    North End
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "clean and great staff "
    Reviewed May 8, 2026
    Roundtrip • Edmonton (YEG) - Boston (BOS)
    YEG - BOS • 1 stop BOS - YEG • 1 stop
    CA $4,342
    CA $2,831
    per traveller
    found 1 day ago
    Boston Harbor Hotel

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
Downtown Boston

Downtown Boston

4.5/5(197 area reviews)

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.

Find hotels in Downtown Boston

Chestnut Hill Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $295 per night from May 21 to May 22
CA $295
CA $390 total
May 21 - May 22
includes taxes & fees
9.6/10 Exceptional! (4,363 reviews)
"Friendly service at the bar and breakfast Buffett was very good. Waitstaff was attentive and promt"

Reviewed on May 18, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from May 25 to May 26
CA $174
CA $203 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (2,622 reviews)
"Some rooms don’t have a bathroom inside of the room and you have to use the bathroom in the hallway. There’s shower toilet in individual stalls. They are constantly cleaning them. The cleanliness was top-notch."

Reviewed on May 19, 2026

The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from May 29 to May 30
CA $246
CA $343 total
May 29 - May 30
includes taxes & fees
9.2/10 Wonderful! (4,651 reviews)
"It was SO expensive."

Reviewed on May 18, 2026

Omni Boston Hotel at the Seaport
See all 3,976 properties in Chestnut Hill
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Chestnut Hill vacation package cost?
You can pick up a vacation package to this top destination 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.