Chestnut Hill Vacations

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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
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

Downtown Boston

4.5/5(2,438 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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
The price is ₩233,085 per night from Jul 1 to Jul 2
₩233,085
₩316,330 total
Jul 1 - Jul 2
includes taxes & fees
9/10 Wonderful! (2,405 reviews)
"The hotel was good, but had a lagging aesthetic. I’ve stayed in many hotels that were older, but you could see the attention to maintaining a beautiful look. This hotel didn’t show that. Otherwise, it was a good stay."

Reviewed on Jun 30, 2026

Hyatt Regency Boston/Cambridge
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is ₩291,434 per night from Jul 5 to Jul 6
₩291,434
₩391,959 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (4,493 reviews)
"We changed our hotel few days before our planned trip to come to seaport boston hotel. And it was a great choice to do.. we do not regret it at all. Stuff were so helpful and kind. Check-in and check-our were very quick and easy. The room was exacatly as seen in the photos. And the major strength ..."

Reviewed on Jun 30, 2026

Seaport Hotel Boston
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 ₩220,753 per night from Jul 5 to Jul 6
₩220,753
₩257,067 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (2,709 reviews)
"Great location!"

Reviewed on Jun 30, 2026

The Revolution Hotel
See all 3,952 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.

Frequently asked questions

How much does a Chestnut Hill vacation package cost?
You can snap up a vacation package to this popular destination on Expedia. However, how much your vacation to Chestnut Hill costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Chestnut Hill?
If you'd like to score a cheap Chestnut Hill vacation package, consider traveling in January, February and November. You'll usually find lower rates on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Chestnut Hill?
The ideal duration of your Chestnut Hill vacation depends on what you'd like to see and do. Typically, a few days to a week will give you plenty of time to hit all the leading attractions and discover some hidden spots along the way.
How to find the best Chestnut Hill package deals?
Start your search for a Chestnut Hill package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Chestnut Hill package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chestnut Hill getaway 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 arranging flights and stays separately. Better still, you can tailor your Chestnut Hill trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Chestnut Hill?
If you have your Chestnut Hill vacation dates locked in, book early to snap up some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Chestnut Hill?

  1. Pick the perfect time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to travel to Chestnut Hill.
  2. Work out your budget: Make sure you have enough money to cover everything from dining out and transportation to airfares and activities. Your accommodations will probably be the largest expense during your trip to Chestnut Hill.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Chestnut Hill. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Chestnut Hill vacation package that brings all your bookings together.

Stay near popular Chestnut Hill attractions

McMullen Museum

6.0/5 (1 review)
This Boston College treasure houses over 5,000 artworks spanning diverse periods and cultures. Explore the serene galleries on Sunday afternoons for free docent-led tours of current exhibitions.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.