Highlands Vacations from ￥176,663

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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 ￥233,152, price is now ￥176,663 per person
￥176,663
per person
Jan 22 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
17.2/10 Exceptional! (1,337 reviews)
Staff were very courteous! Clean room!

Reviewed on Nov 15, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥330,034, price is now ￥224,764 per person
￥224,764
per person
Jan 22 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
19.2/10 Exceptional! (482 reviews)
Staff went above and beyond!

Reviewed on Nov 9, 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was ￥238,725, price is now ￥187,378 per person
￥187,378
per person
Jan 22 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
18/10 Exceptional! (1,094 reviews)
Overall beautiful hotel and kind staff. Very easy to work with and accommodating to our needs!

Reviewed on Nov 14, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was ￥225,164, price is now ￥182,567 per person
￥182,567
per person
Jan 22 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
18.4/10 Exceptional! (1,196 reviews)
The staff was super helpful and kind. We had an early check in, we had to add an extra day and they helped us with that no problem. Travel was seamless despite the air travel nightmares because of the shutdown.

Reviewed on Nov 15, 2025

Hotel Commonwealth

Hotel Commonwealth

4.5 out of 5
Fenway–Kenmore
Price was ￥224,260, price is now ￥183,364 per person
￥183,364
per person
Jan 22 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
18.8/10 Exceptional! (1,839 reviews)
The hotel is updated with modern fixtures. Hotel staff were very friendly. Parking is very expensive though. The room was very clean and housekeeping came every day (a plus). I would definitely stay here again. Conveniently located near metro station which was nice.

Reviewed on Nov 16, 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

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 ￥21,482 per night from Dec 15 to Dec 16
￥21,482
￥25,017 total
Dec 15 - Dec 16
includes taxes & fees
9.2/10 Wonderful! (4,034 reviews)
I had an absolutely wonderful experience during my stay. From the moment I arrived, the staff made me feel welcomed and taken care of. Check-in was quick and easy, and every team member I encountered was friendly, professional, and genuinely eager to help. The room was spotless, beautifully designed, ...

Reviewed on Nov 14, 2025

citizenM Boston North Station
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 ￥25,464 per night from Dec 18 to Dec 19
￥25,464
￥35,982 total
Dec 18 - Dec 19
includes taxes & fees
9/10 Wonderful! (4,198 reviews)
Spacious room that was spotless. Friendly and helpful staff. My favorite place to stay in Boston!

Reviewed on Nov 14, 2025

Omni Boston Hotel at the Seaport
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 ￥11,217 per night from Dec 18 to Dec 19
￥11,217
￥13,063 total
Dec 18 - Dec 19
includes taxes & fees
9/10 Wonderful! (2,234 reviews)
The bathrooms were always well attended to and my room was spotless when I showed! Front desk was also very kind and responsive

Reviewed on Nov 11, 2025

The Revolution Hotel
See all 3,528 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 ￥176,663, 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
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
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

Things to do

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

￥5,190
per adult
86% of travellers recommend
View Boston Observation Deck Admission Tickets
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥12,060
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

￥8,312
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
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.