Chestnut Hill Holidays

Photo by Ed Gaffny

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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
Downtown Boston which includes night scenes and a city as well as a small group of people

Downtown Boston

4.5/5(95 area reviews)

The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

Find hotels in Downtown Boston

Top hotels in Chestnut Hill

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is S$289 per night from 5 Apr to 6 Apr
S$289
5 Apr - 6 Apr
includes taxes & fees
9.2/10 Wonderful! (4,541 reviews)
PERFECT

Reviewed on 24 Mar, 2026

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is S$297 per night from 5 Apr to 6 Apr
S$297
5 Apr - 6 Apr
includes taxes & fees
8.4/10 Very Good! (3,135 reviews)
Best hotel experience I’ve ever had. The complementary waters made all the difference. Having access to an awesome gym was also amazing for people who enjoy fitness and gyms while traveling.

Reviewed on 24 Mar, 2026

Hilton Boston Park Plaza
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 S$245 per night from 5 Apr to 6 Apr
S$245
5 Apr - 6 Apr
includes taxes & fees
9.6/10 Exceptional! (4,092 reviews)
Room was clean. Bathroom sink was not draining well. Took 40 minutes to get our car, which made us late for an appointment. On arrival was told we had a $30 credit from Expedia to use for breakfast or dinner at the restaurant. We decided to have breakfast but was charged $75.00. After several phone ...

Reviewed on 24 Mar, 2026

Seaport Hotel Boston
See all 3,892 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 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.

Popular places to visit

Fenway Park showing a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(62 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University featuring a city and heritage architecture

Harvard University

4.5/5(104 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
New England Aquarium featuring marine life

New England Aquarium

4.5/5(57 reviews)

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

S$66
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

S$100
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

S$106
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
See all activities in Boston

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.