Highlands Vacation Packages

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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Price was CA $917, price is now CA $633 per person
CA $633
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (2,156 reviews)
Absolutely loved it all- hip new vibe. Easy going staff at the ready. Gorgeous rooms and the ‘down the hall bathroom’ was across from room and all amenities perfect. Private bathroom suites. Parking right around the corner. Such a good 24 hours in Boston!

Reviewed on Sep 13, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,848, price is now CA $1,666 per person
CA $1,666
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (159 reviews)
Staff went above and beyond everyday! The dining options and location were amazing.

Reviewed on Sep 2, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was CA $1,306, price is now CA $862 per person
CA $862
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,001 reviews)
It’s still the best hotel in Cambridge

Reviewed on Sep 12, 2025

The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

4 out of 5
Back Bay
Price was CA $1,365, price is now CA $918 per person
CA $918
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,334 reviews)
Great service! From the moment we checked in till the time we checked out we had an amazing experience.

Reviewed on Sep 13, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,058, price is now CA $716 per person
CA $716
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,015 reviews)
Great place for families to stay when moving your young adults to Boston for college or from one apartment to another. Located close to Harvard, MIT, Boston University, Tufts University, Cambridge, Allston, Storrow Drive easy access to drive to Boston MFA and Isabella Stewart Gardner Museum

Reviewed on Sep 13, 2025

Where to stay in Highlands

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

Downtown Boston

4.5/5(193 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 hotels in Downtown Boston

Highlands Hotel Deals

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 CA $365 per night from Sep 21 to Sep 22
CA $365
CA $433 total
Sep 21 - Sep 22
includes taxes & fees
9.6/10 Exceptional! (3,381 reviews)
"Quiet location. Close to public transportation to get all around Boston! Free bikes to explore."

Reviewed on Sep. 10, 2025

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $327 per night from Sep 22 to Sep 23
CA $327
CA $437 total
Sep 22 - Sep 23
includes taxes & fees
9/10 Wonderful! (3,950 reviews)
"It was a nice hotel and great shower pressure"

Reviewed on Sep. 9, 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $269 per night from Sep 21 to Sep 22
CA $269
CA $313 total
Sep 21 - Sep 22
includes taxes & fees
9.2/10 Wonderful! (3,755 reviews)
"Very sleek!"

Reviewed on Sep. 10, 2025

citizenM Boston North Station
See all 3,402 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Highlands vacation package cost?
From as low as CA $633, 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

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

Fenway Park

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

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

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

Harvard University
Boston Common which includes flowers, a garden and landscape views

Boston Common

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

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $109
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $75
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.