Chestnut Hill Vacations from ￥116,762

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The Latest Chestnut Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Seaport District
Save 100% on your flight
Price was ￥174,058, price is now ￥116,762 per person
￥116,762
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.2/10 Wonderful! (2,420 reviews)
I understand things happen but apon reaching my

Reviewed on May 12, 2026

Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Save 100% on your flight
Price was ￥297,289, price is now ￥162,178 per person
￥162,178
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
the hotel was charming and clean and really well located - an easy walk to the common and a longer, but totally doable walk to the major freedom trail sites. the room was european tiny, but plenty sufficient, since we spent our time exploring the city. i only wish the air conditioning was a little more consistent and that there were more outlets so both guests could have phones charging and accessible by the bed, especially as there isn’t a clock in the room.

Reviewed on May 13, 2026

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Save 100% on your flight
Price was ￥212,976, price is now ￥132,905 per person
￥132,905
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (77 reviews)
Very clean rooms. House service actually came twice one to clean up and the other to restock - Luisa and Dilicia were very warm and nice. Staff are very hospitable, right from my arrival to departure

Reviewed on May 12, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was ￥283,860, price is now ￥179,695 per person
￥179,695
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.8/10 Excellent! (1,462 reviews)
Staff on the front desk were absolutely fantastic! The hotel location perfect especially for the TD Gardens. Breakfast is available but we only had once. Shame the bar area wasn't open. Overall, a fantastic hotel that we would highly recommend if you are coming to Boston. Also, super close to the airport making transfers easy.

Reviewed on May 13, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was ￥257,718, price is now ￥174,218 per person
￥174,218
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.4/10 Exceptional! (1,004 reviews)
Excellent location and great staff

Reviewed on May 3, 2026

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

Downtown Boston

4.5/5(2,438 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

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 ￥40,328 per night from May 25 to May 26
￥40,328
￥52,346 total
May 25 - May 26
includes taxes & fees
9.6/10 Exceptional! (4,339 reviews)
The only hiccup we had was a less than helpful staff at the restaurant for dinner. after a brief “discussion” things changed and we had a good meal.

Reviewed on May 13, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is ￥19,975 per night from May 25 to May 26
￥19,975
￥23,262 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (2,602 reviews)
This was such a fun location and a great way for people to share a room and save some money in downtown Boston. We loved the experience, the hotel, and the staff. 10/10. Would stay here again!

Reviewed on May 11, 2026

The Revolution Hotel
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 ￥26,386 per night from May 29 to May 30
￥26,386
￥37,159 total
May 29 - May 30
includes taxes & fees
9.2/10 Wonderful! (4,667 reviews)
This is one of the best decisions I ever made honestly!! They were all so sweet. The hotel was gorgeous and I had written a note for them before coming that it was my birthday and if I could get the highest floor. They had 22 floors and gave me the 20th and not just that but they also had a cup desert ...

Reviewed on May 13, 2026

Omni Boston Hotel at the Seaport
See all 3,974 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 from ￥116,762 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

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Boston College

Take a campus tour or just explore the area of Boston College, during your trip to Boston. Stroll along the riverfront or attend a sporting event in this vibrant area.

Boston College
Fenway Park

Fenway Park

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

Fenway Park
Harvard University

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

Things to do

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

￥5,419
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥13,387
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Harvard Guide leading a tour

Harvard University Campus Guided Walking Tour

￥3,666
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
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.