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.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $2,387, price is now CA $1,580 per person
CA $1,580
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
8.6/10 Excellent! (1,395 reviews)
Just Ok - Great location near the TD Garden so that was great for our plans. Parking felt unsafe in a garage down the street that was suggested and added to our bill. Room was small but comfortable and quiet. Major issue with safety when we returned at night - 2 provocative females were hiding in lobby and bothered us to use our room key to use a bathroom - did not like the NO answer we gave them and it felt very gross honestly - no person at desk at 10:30 PM and was told to email my concern when I spoke to person at desk upon check out. I did email and received a very lame response with no offer to make it right such as money off or a comp stay for future. There are better places in the area with better customer service and safety

Reviewed on Mar 14, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,884, price is now CA $1,812 per person
CA $1,812
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
Best hotel ive ever stayed in.

Reviewed on Mar 11, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $5,485, price is now CA $3,784 per person
CA $3,784
per person
May 14 - May 20
found 20 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Great location within walking distance to many of Boston’s best spots including Faneuil Market, North End “little Italy,” and more! The hotel staff were welcoming and kind during our visit, and our room was well kept. No complaints.

Reviewed on Mar 14, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $4,021, price is now CA $2,820 per person
CA $2,820
per person
May 23 - May 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
9.6/10 Exceptional! (251 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
Price was CA $2,254, price is now CA $1,587 per person
CA $1,587
per person
May 14 - May 20
found 20 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
7/10 Good! (182 reviews)
Perfect location, professional staff, great parking arrangement

Reviewed on Feb 22, 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 showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(193 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 $209 per night from Mar 22 to Mar 23
CA $209
CA $299 total
Mar 22 - Mar 23
includes taxes & fees
9.2/10 Wonderful! (4,512 reviews)
Amazing place

Reviewed on Mar 14, 2026

Omni Boston Hotel at the Seaport
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 $208 per night from Mar 19 to Mar 20
CA $208
CA $298 total
Mar 19 - Mar 20
includes taxes & fees
8.4/10 Very Good! (3,118 reviews)
Second stay here. This is now our go to hotel in Boston. Excellent staff, location, and wonderful lobby/lounge. Can’t wait to return.

Reviewed on Mar 13, 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is CA $209 per night from Mar 20 to Mar 21
CA $209
CA $243 total
Mar 20 - Mar 21
includes taxes & fees
9.2/10 Wonderful! (6,362 reviews)
Hotel was convenient to many tourist attractions. Very friendly staff.

Reviewed on Mar 14, 2026

Harborside Inn Of Boston
See all 3,978 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 $1,580 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

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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.

Boston College
Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

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

Fenway Park
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium

Things to do

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
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
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.