Highlands Vacations from ￥400,392

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥85,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Verb Hotel

The Verb Hotel

3.5 out of 5
Fenway–Kenmore
Price was ￥479,596, price is now ￥400,392 per person
￥400,392
per person
Jun 18 - Jun 23
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (2,044 reviews)
Fun place to stay with all the music 🎶 memorabilia to see. Walking distance to lots of activities.

Reviewed on Apr 26, 2026

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was ￥552,638, price is now ￥451,578 per person
￥451,578
per person
Jun 18 - Jun 23
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (2,298 reviews)
We have stayed at many hotels in Boston. The Colonnade was very comfortable. Large clean rooms and central to everything.

Reviewed on Apr 26, 2026

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
Downtown Boston
Price was ￥504,355, price is now ￥424,818 per person
￥424,818
per person
Jun 18 - Jun 23
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (6,479 reviews)
Staff was beyond expectations

Reviewed on Apr 26, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was ￥696,723, price is now ￥589,992 per person
￥589,992
per person
Jun 18 - Jun 23
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Very nice hotel. Clean, great staff!

Reviewed on Apr 22, 2026

Homewood Suites by Hilton Boston Seaport District

Homewood Suites by Hilton Boston Seaport District

3 out of 5
Seaport District
Price was ￥538,568, price is now ￥462,258 per person
￥462,258
per person
Jun 18 - Jun 23
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (1,456 reviews)
Overall stay was great. Breakfast was extensive and delicious!

Reviewed on Apr 16, 2026

Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
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

Highlands 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 ￥26,959 per night from May 3 to May 4
￥26,959
￥36,830 total
May 3 - May 4
includes taxes & fees
9.6/10 Exceptional! (4,230 reviews)
Clean room!

Reviewed on Apr 27, 2026

Seaport Hotel Boston
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 ￥27,923 per night from May 10 to May 11
￥27,923
￥39,014 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (4,603 reviews)
the pool was great!

Reviewed on Apr 26, 2026

Omni Boston Hotel at the Seaport
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street Boston MA
Fully refundableReserve now, pay when you stay
The price is ￥29,563 per night from May 25 to May 26
￥29,563
￥40,925 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (5,016 reviews)
I love the Godfrey. Stay there almost every time I go to Boston. I have nothing negative to say about it. Staff is great, rooms are spacious, comfortable, and clean. Extra touches like water and snacks in the room are very appreciated.

Reviewed on Apr 26, 2026

The Godfrey Hotel Boston
See all 3,801 properties in Highlands
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 Highlands vacation package cost?
From as low as ￥400,392, you can tailor your Highlands vacation package. Simply combine hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Highlands?
Combine your hotels and flights, add extras such as tours, and save with a Highlands vacation package. You won't just walk away with superb discounts on your escape — you'll have plenty of choice within your reach too. When you book with Expedia, you'll have your pick of over 550 partner airlines and 1,000,000 properties throughout the world. Your affordable vacation begins right here, right now!
Where should I stay in Highlands?
Stay at a hotel near Bentley College. This impressive sight is in the middle of the action and on the must-see lists of many tourists.
How far in advance should I book my Highlands vacation?
Browse Expedia to compare international flights as early as possible. In many cases, you can purchase a seat up to 12 months in advance. If you can't see your preferred carrier, or you've left things to the last minute, don't worry. Cheap fares to Highlands occasionally appear a few weeks before the date of departure.
What does an Expedia Highlands travel package include?
Packages include rental cars, hotels and flights, but you can combine any of them to create your ideal Highlands getaway. You can also add on some activities and experiences once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll enjoy deals you won't find elsewhere.
What should I know before booking a Highlands travel package?
You'll score big savings when you bundle your hotels, flights and rental cars into a travel package. Not only that, booking everything together makes trip planning much easier. So why waste your money or time? Whether you're organizing a fancy romantic getaway or an affordable family break, check out our vacation packages today.
Can I choose my airline with a Highlands Expedia vacation package?
With a vacation package, you're in control. Whether you'd prefer to fly to Highlands in economy or business class, simply select from the available airline options. Expedia has access to more than 550 partner airlines globally.
If I'm not able to travel, can I cancel my Highlands vacation package?
If your vacation plans in Highlands have changed, it's a relief to know that it's possible to cancel your booking. If your booking was made in the last 24 hours, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose fees. To find out more, visit our Customer Service Portal.

Discover the most popular places to visit in Highlands

Fenway Park

Fenway Park

4.5/5(2,543 reviews)

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

Fenway Park
Harvard University

Harvard University

4.5/5(1,983 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
Boston Common

Boston Common

4.5/5(4,846 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

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
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
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
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.