Highlands Vacations from ￥279,900

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The Latest Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was ￥330,508, price is now ￥279,900 per person
￥279,900
per person
Mar 14 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
Awesome space. Close to everything and great price

Reviewed on Jan 22, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was ￥394,530, price is now ￥321,135 per person
￥321,135
per person
Mar 14 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
Everything about this hotel was excellent. The restaurant was awesome. Walking distance to great shopping

Reviewed on Jan 20, 2026

Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
Price was ￥374,276, price is now ￥306,529 per person
￥306,529
per person
Mar 14 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
9/10 Wonderful! (1,891 reviews)
Clean hotel room and phenomenol staff!

Reviewed on Jan 19, 2026

The Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
Back Bay
Price was ￥420,935, price is now ￥350,910 per person
￥350,910
per person
Mar 14 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
9.6/10 Exceptional! (1,218 reviews)
Clean, inviting & perfect.

Reviewed on Jan 21, 2026

The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Price was ￥392,831, price is now ￥332,864 per person
￥332,864
per person
Mar 14 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Boston (BOS)
9.4/10 Exceptional! (4,672 reviews)
Room and facility very clean, very professional

Reviewed on Jan 21, 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 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

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 ￥16,568 per night from Jan 25 to Jan 26
￥16,568
￥24,698 total
Jan 25 - Jan 26
includes taxes & fees
9.6/10 Exceptional! (3,902 reviews)
Front desk and staff amazing and friendly.

Reviewed on Jan 17, 2026

Seaport Hotel Boston
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is ￥16,972 per night from Jan 25 to Jan 26
￥16,972
￥19,765 total
Jan 25 - Jan 26
includes taxes & fees
9.2/10 Wonderful! (6,166 reviews)
lovely staff, clean rooms, what more do you need

Reviewed on Jan 21, 2026

Harborside Inn Of Boston
The Langham, Boston

The Langham, Boston

5 out of 5
250 Franklin St Boston MA
Fully refundableReserve now, pay when you stay
The price is ￥55,940 per night from Feb 22 to Feb 23
￥55,940
￥65,142 total
Feb 22 - Feb 23
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
Room was extremely clean, staff was beyond wonderful and helpful. Our new favorite hotel!

Reviewed on Jan 19, 2026

The Langham, Boston
See all 3,792 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 ￥279,900, 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

Boston Common showcases lush greenery and city skyline under a clear blue sky during a sunny day

Boston Common

4.5/5(4,786 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
Nighttime baseball game at Fenway Park showcasing a vibrant atmosphere in Boston, Massachusetts

Fenway Park

4.5/5(2,499 reviews)

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

Fenway Park
Historic architecture of Harvard University in Cambridge, Massachusetts under clear blue skies

Harvard University

4.5/5(1,966 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

Things to do

Step into a festive winter oasis at Stratus bar this holiday season! Adorned with glittering icicles, sparkling lights, and festive winter elements, this experience is a must must-visit.

View Boston Observation Deck Admission Tickets

￥5,323
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

￥12,491
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Small Group Seafood Tour

Behind Boston’s Lobster Scene: Seaport Seafood Experience

￥8,658
per adult
84% of travellers recommend
Behind Boston’s Lobster Scene: Seaport Seafood Experience
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.