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.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9/10 Wonderful! (2,696 reviews)
Great location and very helpful staff.

Reviewed on Aug. 4, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on Aug. 3, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (132 reviews)
Raffles is the most service oriented hotel we have ever stayed at. This place is amazing!!

Reviewed on Aug. 2, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.4/10 Exceptional! (358 reviews)
The property wasn’t at the level we expected of the Mandarin Oriental, however the location was good and walkable to Bay Bay restaurants and shopping.

Reviewed on Aug. 4, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,016 reviews)
Best place to stay in boston

Reviewed on Aug. 2, 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

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

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 $350 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (3,774 reviews)
"The Omni Hotel chain is great, we had an enjoyable stay, other than having a time limit for the swimming pool. I cannot tell you how frustrating it is to have a child and wife that wanted to spend time at the pool, only to be told that the pool is full and you have to be put on a waiting list to ..."

Reviewed on Aug. 3, 2025

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 $221 per night from Sep 1 to Sep 2
CA $221
CA $314 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (3,191 reviews)
"I would stay here again. Convenient location, decent room with good working amenities, elevators work well, great fitness center."

Reviewed on Jul. 31, 2025

Hilton Boston Park Plaza
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 $303 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,542 reviews)
Return customer
"Clean and comfortable."

Reviewed on Aug. 3, 2025

citizenM Boston Back Bay
See all 3,617 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 $979 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
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

CA $115
per adult
76% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
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.