Chestnut Hill Vacations from ¥236,086

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The Latest Chestnut Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Verb Hotel
Boston Harbor Hotel
Raffles Boston
Hotel AKA Back Bay

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

Chestnut Hill Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ¥24,625 per night from Nov 23 to Nov 24
¥24,625
¥29,441 total
Nov 23 - Nov 24
includes taxes & fees
9.6/10 Exceptional! (3,667 reviews)
I stayed for a work conference and found the location and amenities to be very good.

Reviewed on Nov 5, 2025

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 ¥15,953 per night from Nov 23 to Nov 24
¥15,953
¥18,578 total
Nov 23 - Nov 24
includes taxes & fees
9/10 Wonderful! (2,214 reviews)
Stayed overnight, very clean. However, noisy

Reviewed on Nov 6, 2025

The Revolution Hotel
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
70 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ¥20,495 per night from Nov 30 to Dec 1
¥20,495
¥23,868 total
Nov 30 - Dec 1
includes taxes & fees
9.2/10 Wonderful! (3,994 reviews)
Room was spotless, fun, unique. Checkin staff very friendly and helpful. Neat vibe at Citizen M. Also appreciated the security of dual elevators and 10pm lock as well as a rm number generated anonymously!

Reviewed on Nov 4, 2025

citizenM Boston North Station
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 from ¥236,086 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.

Discover the most popular places to visit in Chestnut Hill

Things to do

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