Highlands Vacations from $386

Book a Hotel + Flight or Car together to unlock savings

Your Highlands Vacation

Organizing your next exciting getaway just got simpler with a vacation package to Highlands. Immerse yourself in the very best this neighborhood has to offer while making nice memories you won't forget. Not sure what to do and see during your trip to Highlands? Nearby attractions such as Bentley College, Brandeis University and Moody Street Historic District are great places to start. Don't just think about it — make it a reality! Book your ideal Highlands vacation with Expedia and travel your way.

The Latest Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
D. Hotel Suites & Spa
Boston Lodge and Suites
Boston Harbor Hotel
citizenM Boston North Station
Raffles Boston

Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands

Highlands Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
$158 nightly
The price is $183 total per night from Sep 1 to Sep 2
$183 total
Sep 1 - Sep 2
Total with taxes and 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
$229 nightly
The price is $267 total per night from Sep 1 to Sep 2
$267 total
Sep 1 - Sep 2
Total with taxes and 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
$184 nightly
The price is $214 total per night from Sep 1 to Sep 2
$214 total
Sep 1 - Sep 2
Total with taxes and 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
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.

Discover the most popular places to visit in Highlands

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.