Chestnut Hill Vacations

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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(2,415 area reviews)

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.

Find hotels in Downtown Boston

Chestnut Hill Hotel Deals

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 NT$8,149 per night from Oct 5 to Oct 6
NT$8,149
NT$9,490 total
Oct 5 - Oct 6
includes taxes & fees
9.2/10 Wonderful! (3,821 reviews)
"Most of the staff were great, though when we were checking in during the pouring rain, we asked about parking and the person was basically clueless, they told us of an app that had me park a half hour walk away, so I walked in the rain, luckily I found a bar to warm up in and have a drink!! lol. ..."

Reviewed on 2025/9/22

citizenM Boston North Station
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 NT$8,271 per night from Sep 28 to Sep 29
NT$8,271
NT$9,783 total
Sep 28 - Sep 29
includes taxes & fees
9.6/10 Exceptional! (3,463 reviews)
"Close to sea"

Reviewed on 2025/9/22

Seaport Hotel Boston
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 NT$7,861 per night from Oct 5 to Oct 6
NT$7,861
NT$10,389 total
Oct 5 - Oct 6
includes taxes & fees
9/10 Wonderful! (4,012 reviews)
"This location is the best in the area close to everything."

Reviewed on 2025/9/19

Omni Boston Hotel at the Seaport
See all 3,625 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 vacation package cost?
You can snap up a vacation package to this popular destination 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

One of the prettiest & highly competitive colleges in the Boston area.

Boston College

Take a campus tour or just explore the area around Boston College, a top college 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

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

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

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

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