Chestnut Hill Vacations from ￥117,591

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The Latest Chestnut Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was ￥154,612, price is now ￥117,591 per person
￥117,591
per person
Nov 21 - Nov 24
found 10 hours ago
Roundtrip flight included
Washington (WAS) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
This is the first time we have stayed at this property. The location, accommodations and staff were fantastic. I was especially impressed by the customer service provided by the staff. Every staff member greeted us personally, asked if we needed anything and invariably wished us a good day. The staff alone made our stay a pleasure-able experience.

Reviewed on Sep 17, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was ￥469,121, price is now ￥294,482 per person
￥294,482
per person
Nov 14 - Nov 19
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (160 reviews)
Best hotel in Boston without question! The staff are exceptional, very friendly and attentive. The masseuses at the spa, especially (I believe her name was) Paula are very skilled and helpful with sore muscles and joints after traveling. La Padrona, Amar, and The Long Bar all have delicious food. I will definitely be back!

Reviewed on Sep 15, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥338,609, price is now ￥248,554 per person
￥248,554
per person
Nov 14 - Nov 19
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (457 reviews)
Everything about this place is right! One of the nicest hotels we've ever stayed at.

Reviewed on Sep 5, 2025

XV Beacon

XV Beacon

5 out of 5
Beacon Hill
Price was ￥393,745, price is now ￥295,162 per person
￥295,162
per person
Nov 14 - Nov 19
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (377 reviews)
Great Staff, very nice room. Ideal location for exploring Boston history and access to the T

Reviewed on Sep 19, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Price was ￥316,186, price is now ￥237,146 per person
￥237,146
per person
Nov 14 - Nov 19
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9/10 Wonderful! (246 reviews)
Was quite noisy with traffic.

Reviewed on Sep 19, 2025

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 ￥32,401 per night from Sep 22 to Sep 23
￥32,401
￥37,732 total
Sep 22 - Sep 23
includes taxes & fees
9.2/10 Wonderful! (3,782 reviews)
Personal experience at citizen M
"Great experience BUT no cups in room, no place to relax except to lie in bed, only one small bench to place suitcase then non place to sit.. pillows too hard"

Reviewed on Sep 16, 2025

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 ￥40,686 per night from Sep 22 to Sep 23
￥40,686
￥48,118 total
Sep 22 - Sep 23
includes taxes & fees
9.6/10 Exceptional! (3,433 reviews)
Business hotel near harbour side
"Although the hotel is located in a lovely area by the harbour side, I did feel it was quite far from a lot of the main places to visit. I enjoy walking but I had to use public transport a lot of the time because the places I wished to visit were quite a trek on foot."

Reviewed on Sep 17, 2025

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 ￥36,100 per night from Sep 22 to Sep 23
￥36,100
￥48,069 total
Sep 22 - Sep 23
includes taxes & fees
9/10 Wonderful! (4,012 reviews)
"This location is the best in the area close to everything."

Reviewed on Sep 19, 2025

Omni Boston Hotel at the Seaport
See all 3,614 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 ￥117,591 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

Alumni Stadium

Catch an event at Alumni Stadium during your trip to Boston. Experience the fascinating museums and acclaimed art scene in this vibrant area.

Alumni Stadium

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥11,728
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

￥8,084
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

￥5,048
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
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.