Highlands Vacation Packages

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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
Studio Allston Hotel

Studio Allston Hotel

4 out of 5
Brighton
Price was CA $2,491, price is now CA $1,685 per person
CA $1,685
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.6/10 Excellent! (1,247 reviews)
It's a nice hotel. Quirky, but it's quiet and conveniently located.

Reviewed on Mar 8, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,884, price is now CA $1,812 per person
CA $1,812
per person
Apr 23 - Apr 26
found 5 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
Best hotel ive ever stayed in.

Reviewed on Mar 11, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $8,298, price is now CA $5,553 per person
CA $5,553
per person
Apr 18 - Apr 25
found 12 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (238 reviews)
I went to raffles Boston for fiancés birthday and I called a week ahead to get the room decorated for her special day and when I showed up the room was not decorated, I then called and said they didn’t decorate the room like I asked so they asked if they could come up during dinner and decorate so I agreed. When we returned from dinner the room was “decorated”, the sign was hanging off the ceiling and decorations taped poorly and just looked awful. Very disappointed considering this is a expensive 5 start hotel

Reviewed on Mar 12, 2026

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
MIT
Price was CA $2,735, price is now CA $1,843 per person
CA $1,843
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (2,266 reviews)
The valet parking is an additional $60.00

Reviewed on Mar 11, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,936, price is now CA $2,104 per person
CA $2,104
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Friendly staff, clean room

Reviewed on Feb 20, 2026

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

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Mar 22 to Mar 23
CA $208
CA $297 total
Mar 22 - Mar 23
includes taxes & fees
9.2/10 Wonderful! (4,507 reviews)
Nice

Reviewed on Mar 11, 2026

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Mar 23 to Mar 24
CA $185
CA $270 total
Mar 23 - Mar 24
includes taxes & fees
8.4/10 Very Good! (3,114 reviews)
Choose the wicked small room and it was perfectly fine for my wife and I.

Reviewed on Mar 12, 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is CA $207 per night from Mar 19 to Mar 20
CA $207
CA $241 total
Mar 19 - Mar 20
includes taxes & fees
9.2/10 Wonderful! (6,347 reviews)
Terrific location for seeing the Boston sites!

Reviewed on Mar 12, 2026

Harborside Inn Of Boston
See all 3,797 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
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Frequently asked questions

How much does a Highlands vacation package cost?
From as low as CA $1,685, 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

4.5/5(305 reviews)

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

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

4.5/5(27 reviews)

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

Gillette Stadium
Boston Common which includes flowers, a garden and landscape views

Boston Common

4.5/5(518 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

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $72
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

CA $32
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
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.