Highlands Vacations from ￥71,920

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The Latest Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Lakeside Inn

Lakeside Inn

2 out of 5
Price was ￥95,740, price is now ￥71,920 per person
￥71,920
per person
Nov 20 - Nov 24
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
7.4/10 Good! (2,162 reviews)
Lovely little property right on the lake. Lots of lovely wild flowers along the shore. Friendly staff, comfy bed. Live music weekend nights at club on site. Plenty of free parking.

Reviewed on Aug 30, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was ￥702,344, price is now ￥423,014 per person
￥423,014
per person
Oct 7 - Oct 12
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Highly recommend! Beautiful and amazing service! Felt like 4 seasons or ritz service!

Reviewed on Aug 30, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was ￥200,086, price is now ￥135,154 per person
￥135,154
per person
Nov 20 - Nov 24
found 19 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
9.2/10 Wonderful! (1,007 reviews)
It was a pleasant stay.

Reviewed on Aug 30, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥577,994, price is now ￥420,398 per person
￥420,398
per person
Oct 7 - Oct 12
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (443 reviews)
Was a great looking hotel. Comfy beds. Updates decor. Strange that there was no cooler/fridge in the room though.

Reviewed on Aug 30, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Price was ￥412,898, price is now ￥307,046 per person
￥307,046
per person
Oct 7 - Oct 12
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8/10 Very Good! (588 reviews)
There was Jack hammering from 7 am to 10 pm. The walls are thin so it was heard even with ear plugs. Also there are literally 4 of everything which seemed to be a big slim pickings. Front desk is not very friendly or helpful.

Reviewed on Aug 30, 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

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
The price is ￥22,499 per night from Sep 1 to Sep 2
￥22,499
￥26,936 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,284 reviews)
"Nice hotel in great location"

Reviewed on Aug 27, 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 ￥28,528 per night from Sep 1 to Sep 2
￥28,528
￥39,214 total
Sep 1 - Sep 2
includes taxes & fees
Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥27,057 per night from Sep 1 to Sep 2
￥27,057
￥31,508 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (3,589 reviews)
"clean room. helpful staff. good transportation in the area."

Reviewed on Aug 30, 2025

citizenM Boston North Station
See all 3,406 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 ￥71,920, 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

￥11,633
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

￥10,333
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

￥5,025
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.