Highlands Vacations

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Your Highlands Vacation

Your next big journey is calling with a vacation package to Highlands. Fun, food and nonstop good times — you're bound to find it in this neighborhood. Begin your trip to Highlands by heading to nearby attractions such as Bentley College, Brandeis University and Moody Street Historic District. Expedia can help you turn your ideal Highlands vacation into reality, no matter your budget or travel plans.

The Latest Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,006 reviews)
I did not appreciate that, as a guest, I was treated as an outsider when I went down to the hotel bar and restaurant. Not only did they remove me from my seat abruptly without hearing me out. The restaurant staff escorted me from the table without even asking if I was there to order. They made me sit in the back room. As I sat in said room, all tables were tended to and cleaned except for one right next to mine. I stared at dirty dishes for the span of my time there. It usually wouldn't be a big deal, however, I would expect a hotel of this caliber to require better etiquette. In addition, I flew from Texas to Boston, for a much-anticipated concert. When asking for directions to the MGM Hall near the baseball stadium, I was instructed to go the complete opposite direction placing me an hour and a half behind schedule. I missed the opener and almost missed the concert as a whole. The front desk, housekeeping, and concierge were amazing, but the fact remains that I never received any sympathy or reparation.

Reviewed on May 28, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Jul 18 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
This is an upscale hotel with excellent amenities and wonderfully helpful and friendly people who kindly made our stay a joy.

Reviewed on May 27, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (274 reviews)
Awesome, awesome, awesome. I could not find another word to describe my stay! Awesome.

Reviewed on May 22, 2024

The Dagny Boston

The Dagny Boston

4 out of 5
Downtown Boston
Save 100% on your flight
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (3,534 reviews)
The Dagny is a 5 min walk from the wharf, an easy 7 min walk to Quincy Market, and a 15 min walk to Boston Commons. It was perfect for our stay.

Reviewed on May 31, 2024

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (279 reviews)
This was one of the best hotel experiences I've had. The staff goes above and beyond to make you feel welcomed. From the Tates cookies and sparkling water available, to the water bottles at the end of the night, they really pay attention to small details, making it a great experience. The rooms were clean and roomy. We ended up walking the entire time in Boston since the hotel was at a great location, but if you plan on driving, keep in mind that you have to call ahead of time to access your car. Would definitely stay again!

Reviewed on May 28, 2024

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 night scenes and a city as well as a small group of people

Downtown Boston

4.5/5(2,415 area reviews)

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.

Find hotel + flight trips in Downtown Boston

Highlands Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is $251 per night from Jun 9 to Jun 10
$251
$322 total
includes taxes & fees
Jun 9 - Jun 10
9/10 Wonderful! (2,122 reviews)
"Room was very clean overall hotel was clean front desk staff was meh not the friendliest but the room was soooooo tiny it was a shoe box and for what I spent the room wasn’t worth the money at all"

Reviewed on May 30, 2024

Omni Boston Hotel at the Seaport
Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is $269 per night from Jun 16 to Jun 17
$269
$318 total
includes taxes & fees
Jun 16 - Jun 17
9.6/10 Exceptional! (2,191 reviews)
"Did not need a car, convenient airport drop-off at hotel. Safe & easy access to Boston"

Reviewed on May 31, 2024

Seaport Hotel Boston
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is $199 per night from Jul 1 to Jul 2
$199
$267 total
includes taxes & fees
Jul 1 - Jul 2
8.8/10 Excellent! (2,672 reviews)
"Great location in the middle of all the historic sites"

Reviewed on May 30, 2024

Omni Parker House
See all 3,031 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.

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Frequently asked questions

How much does a Highlands vacation package cost?
From as low as $530, 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.

Discover the most popular places to visit in Highlands

Image for Fenway Park

Fenway Park

4.5/5(2,499 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Image for Harvard University

Harvard University

4.5/5(1,966 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Image for Boston Common

Boston Common

4.5/5(4,786 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Things to do

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

$30
Per adult
98% of travellers recommend
Bewitched Walking Tour of Salem
Image for Freedom Trail: Small Group Tour of Revolutionary Boston

Freedom Trail: Small Group Tour of Revolutionary Boston

$39
Per adult
100% of travellers recommend
Freedom Trail: Small Group Tour of Revolutionary Boston
See all activities in Boston

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