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.
Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave

2.5 out of 5
South End
per person
Oct 11 - Oct 16
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
7.8/10 Good! (55 reviews)
Easy to walk to and from T stations near by. Decently priced and was overall a great place to stay!

Reviewed on Jul. 23, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 22 - Sep 26
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
Sep 14 - Sep 17
found 2 days ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (349 reviews)
This experience from checking in to the quality of the room and the incredible concierge service that helped us with restaurants in our entire experience was unbelievable! It was probably the best experience I had with a luxury hotel in any city I visited. We will definitely be coming back!

Reviewed on Jul. 20, 2025

The Beverly

The Beverly

3 out of 5
per person
Oct 16 - Oct 20
found 5 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
8.4/10 Very Good! (313 reviews)
Stopped in for overnight stay. Awkward check in as no emailed code (no desk staff on premises), got that worked out. Rooms are comfortable and appeared clean. Couple of places across street to eat and little shopping center, so nice options for quick stay.

Reviewed on Jul. 31, 2025

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

2 out of 5
Back Bay
per person
Oct 11 - Oct 16
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (135 reviews)
Loved the location. The property was great. Only downside is the bathroom is extremely small and I am not a very big individual. There are also a lot of stairs. Which again, not an issue for myself however if you have difficulties with stairs, be prepared. The location was perfect. Close to everything. I would stay again.

Reviewed on Jul. 24, 2025

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

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

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $253 per night from Aug 24 to Aug 25
CA $253
CA $351 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (3,769 reviews)
"Was pleasantly surprised, great hotel and staff."

Reviewed on Jul. 28, 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $261 per night from Aug 10 to Aug 11
CA $261
CA $304 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,510 reviews)
Hip Hotel!
"Great hotel! It’s a hip and trendy place. The room itself was efficient, clean, comfortable and without unnecessary frills. I really liked the blackout curtain! Was in town for Red Sox games and stayed for one night. It was convenient location to Fenway Park as well as plenty of shops and ..."

Reviewed on Jul. 30, 2025

citizenM Boston Back Bay
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $241 per night from Aug 24 to Aug 25
CA $241
CA $280 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (3,610 reviews)
CitizenM never disappoints!
"I love CitizenM and the one in Boston didn't disappoint. The check in staff (it is self check-in, but they always come over to help) and the staff in the "canteen" were wonderfully friendly to a tired traveler."

Reviewed on Jul. 29, 2025

citizenM Boston North Station
See all 3,622 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.
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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 $1,256 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 College

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

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $96
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $46
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
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.