Highlands Holidays

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Your Highlands Holiday

Organising your next exciting getaway just got simpler with a holiday package to Highlands. Immerse yourself in the very best this neighbourhood 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 holiday with Expedia and travel your way.

Our guide on where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
Downtown Boston showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(17 area reviews)

This is Boston’s business district, now and back when the city was just starting.

Find hotels in Downtown Boston

Our pick of the best 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 AU$440 per night from 10 Aug to 11 Aug
AU$440
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (3,695 reviews)
"Room was spacious and clean. The restaurants in the hotel were great, a little costly but delicious food."

Reviewed on 16 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 AU$311 per night from 27 July to 28 July
AU$311
27 July - 28 July
includes taxes & fees
9.2/10 Wonderful! (1,438 reviews)
"loved staying here. there is plenty of space to relax and make time pass by while you explore boston. the rooms were clean and chic. would recommend to a friend :)"

Reviewed on 16 Jul. 2025

citizenM Boston Back Bay
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St, Boston, MA
The price is AU$369 per night from 20 July to 21 July
AU$369
20 July - 21 July
includes taxes & fees
9/10 Wonderful! (5,339 reviews)
"Would highly recommend. The staff was very friendly and helpful. The location was great. The room was very clean, comfortable, and quiet. Will definitely stay here again."

Reviewed on 17 Jul. 2025

Harborside Inn Of Boston
See all 3,396 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Highlands holiday package cost?
From as low as , 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.

Discover the most popular places to visit in Highlands

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

Fenway Park

4.5/5(9 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(27 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 which includes landscape views, a skyscraper and a park

Boston Common

4.5/5(32 reviews)

The oldest public park in the United States, Boston Common is the ideal place to relax, unwind and soak up some history.

Boston Common

Activities

Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

AU$83
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

AU$128
per adult
76% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

AU$46
per traveller
Liberty, Freedom, and Revolution: American History Tours Bundle
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.