
Highlands Holidays
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Price found within the past 48 hours. Click for updated prices.

YOTEL Boston
Seaport District
Save 100% on your flight
per person
10 Sept - 13 Sept
found 19 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
North End
Save 100% on your flight
per person
10 Sept - 13 Sept
found 19 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


The Colonnade Hotel Back Bay
Back Bay
Save 100% on your flight
per person
10 Sept - 13 Sept
found 19 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
Save 100% on your flight
per person
10 Sept - 13 Sept
found 19 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
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.
Top hotels in Highlands

Omni Boston Hotel at the Seaport
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

citizenM Boston Back Bay
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 North Station
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
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
Popular places to visit

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

Harvard University
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

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

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

View Boston Observation Deck Admission Tickets
€29
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.