Highlands Vacation Packages

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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
Lakeside Inn

Lakeside Inn

2 out of 5
Price was CA $1,094, price is now CA $703 per person
CA $703
per person
Oct 29 - Nov 3
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (2,162 reviews)
We stayed for one night. When we arrived the restaurant was just jumping with excitement with families and others singing karaoke. It was a nice welcome. We checked out the pool. It was a little cold but the kids had a quick dip and were happy. The staff was amazing. Such great customer service. From the staff that checked us in, the gentleman that cooked breakfast and the lady that cleaned the rooms. The maintenance man helped us with a little issue faster than my toddler could asking him a million questions which is lightning speed. Checkout was also great! 10/10 would definitely stay here again. Rooms were comfortable, quiet, and clean! Great water pressure for the kids baths and showers.

Reviewed on Aug. 28, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was CA $1,625, price is now CA $956 per person
CA $956
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (490 reviews)
Love the Street Bar!

Reviewed on Aug. 25, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,781, price is now CA $1,651 per person
CA $1,651
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (154 reviews)
I could not fault this hotel in any way. After long days out sightseeing and shopping it was great to get back and relax. This was our first time in Boston so we’re not sure which area was best to stay in. However the hotel’s location in Back Bay was excellent.

Reviewed on Aug. 28, 2025

Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
Price was CA $2,403, price is now CA $1,539 per person
CA $1,539
per person
Oct 13 - Oct 18
found 15 hours ago
Roundtrip flight included
Vancouver (YVR) to Boston (BOS)
8.6/10 Excellent! (1,098 reviews)
Great spot. Friendly helpful staff.

Reviewed on Aug. 25, 2025

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was CA $1,406, price is now CA $911 per person
CA $911
per person
Oct 23 - Oct 27
just found
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (168 reviews)
We’ve been to the Cape many times over the past 20 years. The Sesuit Harbor House was conveniently located off Route 6a, but it was very quiet; you couldn’t hear the traffic at all. Phil and his staff are very attentive and friendly; the continental breakfast in a basket every morning (with local treats) was perfect! We will come back and hopefully with more family members. It was 10/10!

Reviewed on Aug. 25, 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 $212 per night from Sep 1 to Sep 2
CA $212
CA $253 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,276 reviews)
"Clean comfortable room with massive comfy bed. Very conveniently situated for the cruise port. Staff were extremely professional, friendly and helpful."

Reviewed on Aug. 25, 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 $294 per night from Sep 1 to Sep 2
CA $294
CA $399 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (3,870 reviews)
"We stayed for a couple of days at the end of our trip to Boston, the hotel was perfect for relaxing by the pool and a short walk from all the areas we wanted to see whilst visiting."

Reviewed on Aug. 25, 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 $253 per night from Sep 1 to Sep 2
CA $253
CA $295 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (3,709 reviews)
"So modern, clean and comfortable"

Reviewed on Aug. 27, 2025

citizenM Boston North Station
See all 3,406 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 $703, 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
Harvard University which includes a city and heritage architecture

Harvard University

4.5/5(279 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
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

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 $97
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.