Highlands Vacations from NT$16,256

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The Latest Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Boston (BOS)
7.6/10 Good! (374 reviews)
The breakfast was great

Reviewed on 2025/6/25

Sea Mist Resort

Sea Mist Resort

3 out of 5
Save 100% on your flight
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Boston (BOS)
8.8/10 Excellent! (124 reviews)
Great place just had another family staying above our room that was very noisy the last night we were there

Reviewed on 2025/6/2

Holly Tree Resort

Holly Tree Resort

3 out of 5
Save 100% on your flight
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Boston (BOS)
9/10 Wonderful! (344 reviews)
The staff is incredibly kind. One of our a/c wasn’t working and they replaced it with a new one with minutes of reporting it The property is clean but there is no housekeeping so you have to take towels etc to the front desk and receive new ones. I felt very safe there. Something I didn’t know was that they have condominiums for rent but you have to call the hotel directly for dates. They have racquetball center which is nice. Light does come through the doorways at night like others have said. Overall I would come here again and it was a good value for the price (except June/July/Aug when prices are close to double! You won’t be disappointed.

Reviewed on 2025/6/23

Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Boston (BOS)
7.8/10 Good! (715 reviews)
The staff were kind. My son and I enjoyed our stay. I would recommend more attention payed to the cleanliness of the pools. I do understand staff is busy doing other things. The first day we arrived we discovered something we would rather not have in the outdoor pool.. not their fault. I have had a bacterial skin infection since I got home. I am not blaming them as I’m not sure where I got it…The pool is beautiful at night and lit up by LED lights the rooms are nice and bright and everyone was nice. The kids all had plenty of space to swim and play. It was a welcoming environment.

Reviewed on 2025/6/24

Sandwich Inn and Suites

Sandwich Inn and Suites

2.5 out of 5
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Boston (BOS)
9/10 Wonderful! (971 reviews)
Great, cozy, clean cottage style inn. Wonky moment when we tried to call for an early check in but was told we couldn't be connected via reservations. Somehow we got through but could get an early check in. Phone access to staff was limited. Otherwise great stay. Nice breakfast!

Reviewed on 2025/6/19

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 NT$6,264 per night from Jul 20 to Jul 21
NT$6,264
NT$8,481 total
Jul 20 - Jul 21
includes taxes & fees
9/10 Wonderful! (3,610 reviews)
"Door are so loud that we were awakened every time anyone on the hall came or went. Kablam! Kablam! I’m sure the doors are self-closing for fire safety reasons, but I’d pay extra to make the doors quiet-close."

Reviewed on 2025/6/25

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 NT$6,195 per night from Jul 3 to Jul 4
NT$6,195
NT$8,092 total
Jul 3 - Jul 4
includes taxes & fees
8.4/10 Very Good! (1,111 reviews)
"Pleasant and attentive employees from the front desk to the restaurant, bar and cleaning staff. They were able to retrieve my phone charger (as I had left it in the room) 4 hours after check out. Kindly held our bags prior to departure. Great location and view from our room. I would definitely recommend ..."

Reviewed on 2025/6/22

Hilton Boston Back Bay
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is NT$4,052 per night from Jul 6 to Jul 7
NT$4,052
NT$4,718 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (1,311 reviews)
"Very cool and modern!"

Reviewed on 2025/6/26

citizenM Boston Back Bay
See all 3,349 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 NT$16,256, 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.