Chestnut Hill Holidays

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Price found within the past 48 hours. Click for updated prices.
Global Luxury Suites Downtown Boston
Boston Harbor Hotel
Raffles Boston
Encore Boston Harbor
The Whitney Hotel

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

Top hotels in Chestnut Hill

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 €222 per night from 24 Aug to 25 Aug
€222
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,769 reviews)
"Was pleasantly surprised, great hotel and staff."

Reviewed on 28 Jul 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 €193 per night from 10 Aug to 11 Aug
€193
10 Aug - 11 Aug
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 30 Jul 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 €177 per night from 24 Aug to 25 Aug
€177
24 Aug - 25 Aug
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 29 Jul 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 holiday package cost?
You can snap up a holiday package to this popular destination from €953 on Expedia. However, how much your holiday 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 holiday package, consider travelling 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 holiday 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 holiday as a package?
An Expedia holiday 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 holiday package to Chestnut Hill?
If you have your Chestnut Hill holiday 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, favourite 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 accommodation 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 holiday package that brings all your bookings together.

Things to do

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