Chestnut Hill Vacation Packages

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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.

Top Holiday Package Deals in Chestnut Hill

Price found within the past 48 hours. Click for updated prices.
The Westin Waltham-Boston

The Westin Waltham-Boston

4 out of 5
Price was CA $1,897, price is now CA $1,347 per person
CA $1,347
per person
Jun 13 - Jun 17
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Boston (BOS)
8.8/10 Excellent! (1,095 reviews)
Good service , Clean rooms

Reviewed on Mar 30, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $6,088, price is now CA $3,918 per person
CA $3,918
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (238 reviews)
The photos doesn’t give this place justice.

Reviewed on Mar 24, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $2,965, price is now CA $1,967 per person
CA $1,967
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8.6/10 Excellent! (1,395 reviews)
Great hotel, in the middle of downtown, walking distance from td garden, friendly staff and great amenities, will be back for sure

Reviewed on Mar 30, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,479, price is now CA $1,673 per person
CA $1,673
per person
Jun 13 - Jun 17
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
Price was CA $2,305, price is now CA $1,641 per person
CA $1,641
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8.6/10 Excellent! (1,001 reviews)
Staff was very friendly and the room was clean and comfortable. It will be even better when they offer breakfast!

Reviewed on Mar 31, 2026

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

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 $215 per night from Apr 5 to Apr 6
CA $215
CA $307 total
Apr 5 - Apr 6
includes taxes & fees
9.2/10 Wonderful! (4,549 reviews)
Very nice

Reviewed on Mar 28, 2026

Omni Boston Hotel at the Seaport
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 $177 per night from Apr 5 to Apr 6
CA $177
CA $254 total
Apr 5 - Apr 6
includes taxes & fees
9.6/10 Exceptional! (4,116 reviews)
Clean rooms and great location

Reviewed on Mar 31, 2026

Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $249 per night from Apr 5 to Apr 6
CA $249
CA $347 total
Apr 5 - Apr 6
includes taxes & fees
8.4/10 Very Good! (3,136 reviews)
The heater was so loud, I couldn’t sleep well.

Reviewed on Apr 1, 2026

Hilton Boston Park Plaza
See all 3,866 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 from CA $1,347 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.

Discover the most popular places to visit in Chestnut Hill

Boston_BostonCollege_6092291_05

Boston College

4/5(15 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.

Boston College
Fenway Park

Fenway Park

4.5/5(310 reviews)

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

Fenway Park
Harvard University

Harvard University

4.5/5(283 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $72
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $115
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

CA $32
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.