Highlands Vacations from ￥274,261

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The Latest Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
per person
Aug 31 - Sep 5
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8/10 Very Good! (562 reviews)
Very clean and nice! I love that Boston is rennovating building space for airport use - very needed.

Reviewed on Jun 10, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Aug 10 - Aug 14
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Location for first time Boston visitors was really good as a lot area to explore by foot then you could Uber the rest. The staff and in-room dining was outstanding

Reviewed on Jun 16, 2025

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
per person
Aug 10 - Aug 14
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.6/10 Excellent! (1,595 reviews)
Beautiful view. Good location

Reviewed on Jun 16, 2025

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
Seaport District
per person
Aug 10 - Aug 14
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (2,978 reviews)
Rooms are very clean

Reviewed on Jun 19, 2025

Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
per person
Aug 10 - Aug 14
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.8/10 Excellent! (1,865 reviews)
Nice property. Great location. Nice roof top bar and nice restaurant.

Reviewed on Jun 21, 2025

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

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 ￥27,932 per night from Jul 19 to Jul 20
￥27,932
￥38,482 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (3,572 reviews)
"Nice stay and atmosphere in the lobby"

Reviewed on Jun 21, 2025

Omni Boston Hotel at the Seaport
Hilton Boston Back Bay
Hilton Boston Back Bay
4 out of 5
40 Dalton St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥28,436 per night from Jun 29 to Jun 30
￥28,436
￥37,497 total
Jun 29 - Jun 30
includes taxes & fees
8.4/10 Very Good! (1,114 reviews)
"Everything was excellent. The breakfast buffet was fresh and delicious with a wide variety of options. I especially enjoyed the made-to-order omelets. I would definitely stay here again and highly recommend it to anyone visiting the area."

Reviewed on Jun 14, 2025

Hilton Boston Back Bay
Copley Square Hotel, a FOUND Hotel
Copley Square Hotel, a FOUND Hotel
4 out of 5
47 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥20,679 per night from Jul 2 to Jul 3
￥20,679
￥24,080 total
Jul 2 - Jul 3
includes taxes & fees
8.4/10 Very Good! (3,708 reviews)
Exactly what I was looking for
"Convenient location, friendly front desk staff. Called ahead of time to confirm my reservation and the person I spoke with was courteous and professional. Didn't use any of the amenities so can't comment there. Only here for a night but it met all my (admittedly basic) needs. By far the best price ..."

Reviewed on Jun 20, 2025

Copley Square Hotel, a FOUND Hotel
See all 3,362 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 ￥274,261, 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 which includes a sporting event and night scenes as well as a large group of people

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
Harvard University showing a city and heritage architecture

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
Boston Common featuring landscape views, a skyscraper and flowers

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

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥11,423
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

￥10,147
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

￥3,871
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.