Chestnut Hill Holidays

Book a Hotel + Flight or Car together to unlock savings

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 a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 area reviews)

Known for its must-see aquarium and captivating waterfront views, there's plenty to explore in Downtown Boston. Check out top attractions like Boston Harbor and Boston Massacre Site, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

Find hotels in Downtown Boston

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 5.008.484 ₫ per night from 19 Jul to 20 Jul
5.008.484 ₫
6.900.087 ₫ 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 5.530.626 ₫ per night from 3 Jul to 4 Jul
5.530.626 ₫
7.224.345 ₫ total
3 Jul - 4 Jul
includes taxes & fees
8.4/10 Very Good! (1,118 reviews)
"Pleasant and attentive employees from the front desk to the restaurant, bar and cleaning staff. They were able to retrieve my phone charger (as I had left it in the room) 4 hours after check out. Kindly held our bags prior to departure. Great location and view from our room. I would definitely recommend ..."

Reviewed on 22 Jun 2025

Hilton Boston Back Bay
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 3.750.914 ₫ per night from 29 Jun to 30 Jun
3.750.914 ₫
4.367.939 ₫ total
29 Jun - 30 Jun
includes taxes & fees
9.2/10 Wonderful! (1,283 reviews)
"Our room has a weird noise associated with A/C. And it only occurred on the 3rd night. Bothered too much so had to switch to a new room"

Reviewed on 22 Jun 2025

citizenM Boston Back Bay
See all 3,573 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

Boston College

Boston College

4/5(5 reviews)

Walk around the campus of Boston College, a top university in Boston. Stroll along the riverfront or attend a sporting event in this vibrant area.

Boston College
Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(61 reviews)

Fenway Park is one of the more well-known attractions to visit during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(102 reviews)

Take a campus tour or just explore the area around Harvard University, a top university in Boston. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

Harvard University