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 Chestnut Hill Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Studio Allston Hotel
The Langham, Boston
The Inn at Hastings Park, Relais & Chateaux - Boston
Boston Harbor Hotel
The Whitney Hotel

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Chestnut Hill Hotel Deals

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 $219 per night from May 4 to May 5
CA $219
CA $255 total
includes taxes & fees
May 4 - May 5
8.8/10 Excellent! (1,949 reviews)
"The staff were friendly and knowledgeable. One staff member even gave me some electrical tape so I could put my name on my singlet for the marathon."

Reviewed on Apr. 29, 2025

The Revolution Hotel
Four Points by Sheraton Boston Newton
Four Points by Sheraton Boston Newton
3.5 out of 5
320 Washington Street, Newton, MA
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from May 4 to May 5
CA $148
CA $165 total
includes taxes & fees
May 4 - May 5
8.2/10 Very Good! (2,795 reviews)
"Skip"

Reviewed on Apr. 28, 2025

Four Points by Sheraton Boston Newton
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 May 11 to May 12
CA $261
CA $303 total
includes taxes & fees
May 11 - May 12
9.4/10 Exceptional! (1,066 reviews)
"It was very small but very nice and comfortable"

Reviewed on Apr. 30, 2025

citizenM Boston Back Bay
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.

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 $983 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

What to do in Chestnut Hill

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.