Highlands Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Highlands

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

Downtown Boston

4.5/5(94 area reviews)

Known for its must-see aquarium and captivating waterfront views, there's plenty to explore in Downtown Boston. Check out top attractions like Boston Massacre Site and Old State House, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

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Top hotels in Highlands

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
9.2/10 Wonderful! (6,196 reviews)
Staff was extremely nice and helpful. Hotel was beautiful and clean. We also liked how they had an onsite restaurant which was delicious.

Reviewed on 31 Jan 2026

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Harborside Inn Of Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (2,432 reviews)
I chose this hotel last minute, we had an emergency in the family that needed us to stay in the Boston area. Reserving was easy, and the price totally reasonable, ESPECIALLY due to the last minute nature of the reservation. Beautiful hotel, with a lovely coffee shop in the lobby! The room was spacious, ...

Reviewed on 30 Jan 2026

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The Revolution Hotel
The Langham, Boston

The Langham, Boston

5 out of 5
250 Franklin St Boston MA
Fully refundableReserve now, pay when you stay
The price is 9.730.875 ₫ per night from 6 Feb to 7 Feb
9.730.875 ₫
11.331.604 ₫ total
6 Feb - 7 Feb
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
Very nice hotel with excellent staff.

Reviewed on 28 Jan 2026

The Langham, Boston
See all 3,837 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.

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 1null000null000 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.

Popular places to visit

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

Fenway Park

4.5/5(61 reviews)

Catch an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

3/5(2 reviews)

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's acclaimed theatre scene and great live music.

Gillette Stadium
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(102 reviews)

Take a campus tour or just explore the area around Harvard University, a top university in Boston. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.

Harvard University