Highlands Vacation Packages

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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Aug. 25 - Aug. 28
found 3 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (2,257 reviews)
Everything was nice.

Reviewed on Jun. 11, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Jul. 31 - Aug. 4
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Absolutely wonderful!

Reviewed on Jun. 11, 2024

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
per person
Jul. 31 - Aug. 6
just found
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
10/10 Exceptional! (4 reviews)
Everything was perfect

Reviewed on May 28, 2024

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Save 100% on your flight
per person
Jul. 31 - Aug. 4
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
8.4/10 Very Good! (3,336 reviews)
Excellent service, "wicked small" room as advertised, great location

Reviewed on Jun. 12, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 29 - Sep. 2
found 2 days ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.4/10 Exceptional! (34 reviews)
Beautiful hotel, flowers in All areas. Staff was superb. Two very minor issue - no fan for toilet area, hot water in shower takes a bit. Doesn’t distract from my overall rating. Easily a come back recommendation

Reviewed on May 29, 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(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 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 CA $273 per night from Jul. 4 to Jul. 5
CA $273
CA $358 total
includes taxes & fees
Jul 4 - Jul 5
9/10 Wonderful! (2,172 reviews)
"Nice property and amenities. Strange that guests need to "reserve" time at the pool. It also seemed strange that there was no pool access for guests in the morning they were checking out. Nice workout facility. Treadmills face a glass wall so if you're running in the morning on a sunny day bring ..."

Reviewed on Jun. 13, 2024

Omni Boston Hotel at the Seaport
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 CA $234 per night from Jul. 4 to Jul. 5
CA $234
CA $321 total
includes taxes & fees
Jul 4 - Jul 5
8.8/10 Excellent! (2,687 reviews)
"Everything was great!"

Reviewed on Jun. 10, 2024

Omni Parker House
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 $251 per night from Jun. 16 to Jun. 17
CA $251
CA $293 total
includes taxes & fees
Jun 16 - Jun 17
8.6/10 Excellent! (1,531 reviews)
"It’s renovated beautifully quite and clean."

Reviewed on Jun. 11, 2024

The Revolution Hotel
See all 2,951 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.

Explore other types of vacation packages

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 $859, 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(305 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(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
Image for Gillette Stadium

Gillette Stadium

4.5/5(27 reviews)

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

Gillette Stadium

Things to do

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $107
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

CA $41
Per adult
98% of travellers recommend
Bewitched Walking Tour of Salem
Image for Odyssey Boston Premier Elegant Dinner Cruise

Odyssey Boston Premier Elegant Dinner Cruise

CA $294
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
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.