Highlands Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Breakfast meal
    Jul 31 - Aug 3

    By the Sea Guests Bed & Breakfast & Suites + Flight

    Dennis Port
    3 nights
    3.5 star property
    9.2/10 - Wonderful (185 reviews)
    "."
    Reviewed October 16, 2025
    Roundtrip • Toronto (YTZ) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YTZ • Nonstop
    CA $1,593
    CA $1,076
    per traveller
    found 1 day ago
    By the Sea Guests Bed & Breakfast & Suites
  • Standard Room, 1 Queen Bed
    Jul 25 - Jul 31

    Hotel Ivy Boston Common + Flight

    Bay Village
    6 nights
    2.5 star property
    8.4/10 - Very good (1,456 reviews)
    "For the money, can non go wrong with this choice"
    Reviewed May 23, 2026
    Roundtrip • Edmonton (YEG) - Boston (BOS)
    YEG - BOS • 1 stop BOS - YEG • 1 stop
    CA $2,580
    CA $1,535
    per traveller
    found 1 day ago
    Hotel Ivy Boston Common
  • Lobby
    Jul 11 - Jul 18

    Nantucket Inn + Flight

    Nantucket
    7 nights
    3.5 star property
    9.2/10 - Wonderful (690 reviews)
    "The shuttle goes downtown so often and the staff is amazing"
    Reviewed May 22, 2026
    Roundtrip • Toronto (YTZ) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $6,842
    CA $4,395
    per traveller
    found 1 day ago
    Nantucket Inn
  • Miscellaneous
    Jul 8 - Jul 12

    Raffles Boston + Flight

    Back Bay
    4 nights
    5.0 star property
    9.6/10 - Exceptional (264 reviews)
    "didn't meet expectation"
    Reviewed May 18, 2026
    Roundtrip • Toronto (YTZ) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YTZ • Nonstop
    CA $4,357
    CA $2,892
    per traveller
    found 1 day ago
    Raffles Boston
  • Lobby
    Jul 25 - Jul 31

    Fairmont Copley Plaza, Boston + Flight

    Back Bay
    6 nights
    4.5 star property
    9.0/10 - Wonderful (1,241 reviews)
    "Gorgeous hotel in a fabulous location. Highly recommend!"
    Reviewed May 19, 2026
    Roundtrip • Edmonton (YEG) - Boston (BOS)
    YEG - BOS • 1 stop BOS - YEG • 1 stop
    CA $2,883
    CA $1,944
    per traveller
    found 1 day ago
    Fairmont Copley Plaza, Boston

Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
Downtown Boston

Downtown Boston

4.5/5(197 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
The price is CA $285 per night from May 29 to May 30
CA $285
CA $379 total
May 29 - May 30
includes taxes & fees
9.6/10 Exceptional! (4,363 reviews)
"Great hotel in a great location."

Reviewed on May 23, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Jun 7 to Jun 8
CA $227
CA $264 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (2,628 reviews)
"Everything is fantastic"

Reviewed on May 22, 2026

The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
The price is CA $242 per night from May 29 to May 30
CA $242
CA $338 total
May 29 - May 30
includes taxes & fees
9.2/10 Wonderful! (4,652 reviews)
"Clean room"

Reviewed on May 23, 2026

Omni Boston Hotel at the Seaport
See all 3,784 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
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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.

Discover the most popular places to visit in Highlands

Fenway Park

Fenway Park

4.5/5(310 reviews)

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

Fenway Park
Harvard University

Harvard University

4.5/5(284 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
Gillette Stadium

Gillette Stadium

4.5/5(28 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

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $79
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
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 CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $115
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
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.