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

A nighttime street scene with illuminated trees, a market stall, and historic buildings.

Downtown Boston

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

A historic building with ornate architecture, a staircase, and a tree in front.

Back Bay

1 out of top 10 points of interest in this area

Gourmet restaurants interesting history and top sights from Copley Square to Newbury Street – discover Back Bay, a destination also famous for its shopping.

A city skyline with modern high-rise buildings, a historic bridge, and a river with boats.

Seaport District

1 out of top 10 points of interest in this area

Travellers to Seaport District praise its captivating waterfront views. If you've got some more time to explore, be sure to stop by Boston Harbor and Liberty Wharf.

A street lamp with a lit bulb, surrounded by trees and a brick building.

Beacon Hill

1 out of top 10 points of interest in this area

Historical sites, shopping and restaurants highlight some notable features of Beacon Hill. Make a stop by Acorn Street or Charles Street while you're visiting, and jump aboard the metro at Charles-MGH Station or Park St. Station to get around town.

A bustling riverside area with a prominent building featuring a large arched entrance, a dock with a boat, and a crowd of people.

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

Seaport Hotel Boston

1 Seaport Lane Boston MA

Fully refundableReserve now, pay when you stay

4.949.140 ₫

6.656.239 ₫ total

30 Aug - 31 Aug

includes taxes & fees

The Revolution Hotel

40 Berkeley Street Boston MA

Fully refundableReserve now, pay when you stay

3.562.438 ₫

4.148.460 ₫ total

24 Aug - 25 Aug

includes taxes & fees

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Fully refundableReserve now, pay when you stay

5.738.437 ₫

7.749.465 ₫ total

30 Aug - 31 Aug

includes taxes & fees

See all 3,745 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.