Highlands Holidays
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- Better togetherSave up to €900 when you book a flight and hotel together*
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Price found within the past 48 hours. Click for updated prices.
Where to stay in Highlands
Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
Downtown Boston
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.
Back Bay
1 out of top 10 points of interest in this area
Parisian boulevards and elegant brownstones conjure a truly romantic atmosphere, perfect for strolling and window shopping.
Seaport District
1 out of top 10 points of interest in this area
Join excited crowds enjoying harbor-side views, Revolutionary War-era landmarks, as well as superb restaurants and museums along this thriving waterfront.
Beacon Hill
1 out of top 10 points of interest in this area
Lose yourself in the charming streetscapes, historic buildings and village-like 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 New England Aquarium while you're visiting, and jump aboard the metro at Aquarium to get around town.
Top hotels in Highlands
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
€294
20 Sept - 21 Sept
includes taxes & fees
9.2/10 Wonderful! (4,816 reviews)
"The room was clean and nice and the hotel has an upscale vibe which I liked. The staff at the front desk were very polite and helpful when needed. The property is a 10 minute car ride to downtown or walking distance to some shopping places or restaurants at the commonwealth pier area. You can also ..."
Reviewed on 13 Sept 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
€299
20 Sept - 21 Sept
includes taxes & fees
9.6/10 Exceptional! (4,976 reviews)
"The staff were very efficient and helpful, The rooms were clean and nicely appointed. The location on the wharf is excellent. We would stay there again."
Reviewed on 13 Sept 2026
The Revolution Hotel
40 Berkeley Street Boston MA
€216
20 Sept - 21 Sept
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 €1,170, 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.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
€42
per adult
90% of travellers recommend
View Boston Observation Deck General Admission
€29
per adult
Boston Freedom Trail Walking Tour with Costumed Guide
€22
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.