Chestnut Hill Holidays

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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

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 Rp3.135.106 per night from 19 Jul to 20 Jul
Rp3.135.106
Rp4.319.174 total
19 Jul - 20 Jul
includes taxes & fees
9/10 Wonderful! (3,572 reviews)
"Nice stay and atmosphere in the lobby"

Reviewed on 21 Jun 2025

Omni Boston Hotel at the Seaport
Hilton Boston Back Bay
Hilton Boston Back Bay
4 out of 5
40 Dalton St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is Rp3.191.676 per night from 29 Jun to 30 Jun
Rp3.191.676
Rp4.208.617 total
29 Jun - 30 Jun
includes taxes & fees
8.4/10 Very Good! (1,114 reviews)
"Everything was excellent. The breakfast buffet was fresh and delicious with a wide variety of options. I especially enjoyed the made-to-order omelets. I would definitely stay here again and highly recommend it to anyone visiting the area."

Reviewed on 14 Jun 2025

Hilton Boston Back Bay
Copley Square Hotel, a FOUND Hotel
Copley Square Hotel, a FOUND Hotel
4 out of 5
47 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
The price is Rp2.320.995 per night from 2 Jul to 3 Jul
Rp2.320.995
Rp2.702.798 total
2 Jul - 3 Jul
includes taxes & fees
8.4/10 Very Good! (3,705 reviews)
"Room was comfortable, staff pleasant. Bar overly expensive. Ok for an overnight, convenient location."

Reviewed on 18 Jun 2025

Copley Square Hotel, a FOUND Hotel
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 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.