Highlands Holidays

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Price found within the past 48 hours. Click for updated prices.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
10 Sept - 13 Sept
found 20 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
8.6/10 Excellent! (2,098 reviews)
Located in a new neighborhood with lots of dining options and easy access to public transportation.

Reviewed on 28 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
10 Sept - 13 Sept
found 20 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I would say this is one of the best hotel I've stayed in my life!! The room had an amazing harbor view and nice chair, comfortable bed and best amenities!! The stuff was super nice too. Definitely 5 stars!!!

Reviewed on 28 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
10 Sept - 13 Sept
found 20 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on 14 Jul 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
per person
10 Sept - 13 Sept
found 20 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
9/10 Wonderful! (1,964 reviews)
Great stay. Rooftop pool and easy access to multiple T stops for walking. Only complaint was the shower had water underneath the tub and it inpacted our ability to shower before dinner. However maintenance quickly resolved the issue, although with only a short term fix.

Reviewed on 27 Jul 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
10 Sept - 13 Sept
found 20 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
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Reviewed on 28 Jul 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 featuring a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 area reviews)

The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

Find hotels in Downtown Boston

Top hotels in Highlands

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 €216 per night from 24 Aug to 25 Aug
€216
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,755 reviews)
Outstanding Omni
"Outstanding stay. There’s not one thing that could have been better. I would highly recommend this hotel."

Reviewed on 27 Jul 2025

Omni Boston Hotel at the Seaport
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 €187 per night from 10 Aug to 11 Aug
€187
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (1,496 reviews)
"I like almost everything but breakfast was not good and fruit was not fresh. Also bar does not serve good food so there is a room for huge improvement in this area."

Reviewed on 26 Jul 2025

citizenM Boston Back Bay
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 €173 per night from 24 Aug to 25 Aug
€173
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (3,593 reviews)
"Best hotel we stayed at on our vacation"

Reviewed on 27 Jul 2025

citizenM Boston North Station
See all 3,400 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 holiday package cost?
From as low as €546, you can tailor your Highlands holiday 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 holiday 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 holiday 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 holiday?
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 organising a fancy romantic getaway or an affordable family break, check out our holiday packages today.
Can I choose my airline with a Highlands Expedia holiday package?
With a holiday 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 holiday package?
If your holiday 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.

Popular places to visit

Fenway Park showing night scenes and a sporting event as well as a large group of people

Fenway Park

4.5/5(61 reviews)

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

Fenway Park
Harvard University which includes heritage architecture and a city

Harvard University

4.5/5(102 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
New England Aquarium

New England Aquarium

4.5/5(57 reviews)

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

€68
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

€60
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

€29
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.