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
This is Boston’s business district, now and back when the city was just starting.
Back Bay
1 out of top 10 points of interest in this area
Head to Back Bay for Victorian brownstone homes, hip coffee joints and a shopping district that rivals Manhattan’s 5th Avenue.
Seaport District
1 out of top 10 points of interest in this area
Once known as strong working-class neighbourhood, South Boston has turned into a haven for young professionals.
Beacon Hill
1 out of top 10 points of interest in this area
Take a walk through the charming streets, historic buildings and small-town atmosphere of Boston’s oldest and wealthiest suburbs.
North End
The ample dining options and captivating waterfront views are just a few popular features of the neighbourhood. Make a stop by Boston Harbor or Old North Church while you're visiting, and jump aboard the metro at Aquarium to get around town.
Our pick of the best Highlands Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
AU$652
2 Oct - 3 Oct
includes taxes & fees
9.2/10 Wonderful! (4,836 reviews)
"hotel and room were clean, staff friendly and helpful. top notch atmosphere. we at lunch at the roof top restaurant and it was very good with views of the city. great place to stay in the city. My wife and I loved it"
Reviewed on 24 Sept 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
AU$392
1 Oct - 2 Oct
includes taxes & fees
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
AU$569
4 Oct - 5 Oct
includes taxes & fees
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 , 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.
Activities
Boston Old Town Trolley Hop-on Hop-Off City Tour
AU$68
per adult
90% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
AU$51
per adult
92% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
AU$65
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.