Highlands Vacations

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Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most.
Quincy Market with an American flag, historic buildings, and a clock tower in the background.

Downtown Boston

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.

A historic church with a large central tower and multiple spires, surrounded by modern buildings and a public square with people and greenery.

Back Bay

Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.

A city skyline at dusk with illuminated buildings reflecting on the water, a prominent bridge, and a large chain barrier along the waterfront.

Seaport District

Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.

A large brick building with a golden dome, a flagpole with the American flag, and a statue in front.

Beacon Hill

Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.

A statue of a man on horseback in a park with trees, a clock tower, and brick buildings in the background.

North End

Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.

Highlands Hotel Deals

A modern restaurant with large windows, leather seating, and a bar area.

The Westin Waltham-Boston

The Westin Waltham-Boston
4.0 star property
1.5 km from Highlands
8.8 out of 10, Excellent, (1,159 reviews)
"Bathroom lighting was not great and for a junior suite the bathroom was very small. TV in living space did not work."
The price is ￥17,249
￥19,267 total
includes taxes & fees
Nov 22 - Nov 23
The Westin Waltham-Boston
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.
See all properties in Highlands

Frequently Asked Questions

How much does a Highlands vacation package cost?

From as low as , you can tailor your Highlands vacation 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 vacation 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 vacation 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 vacation?

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 organizing a fancy romantic getaway or an affordable family break, check out our vacation packages today.

Can I choose my airline with a Highlands Expedia vacation package?

With a vacation 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 vacation package?

If your vacation 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.