Highlands Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
The air conditioner sound like a truck trailer was in your room

Reviewed on Jul. 11, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Not bad at all, but nothing special

Reviewed on Jul. 13, 2025

Where to stay in Highlands

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

Though South Lowell might not have many top sights, you can venture to the surrounding area to see attractions like Lowell Memorial Auditorium and Lowell National Historical Park.

Find hotels in South Lowell

Highlands Hotel Deals

Embassy Suites by Hilton Boston Waltham
Embassy Suites by Hilton Boston Waltham
3.5 out of 5
550 Winter Street, Waltham, MA
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Jul 27 to Jul 28
CA $177
CA $198 total
Jul 27 - Jul 28
includes taxes & fees
7.8/10 Good! (2,104 reviews)
"Great stay"

Reviewed on Jul. 12, 2025

Embassy Suites by Hilton Boston Waltham
Bedford Plaza Hotel - Boston
Bedford Plaza Hotel - Boston
2.5 out of 5
340 Great Road, Bedford, MA
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Jul 14 to Jul 15
CA $129
CA $145 total
Jul 14 - Jul 15
includes taxes & fees
7.2/10 Good! (318 reviews)
"If you are looking for a solid place to sleep with nothing fancy at all at a good deal, this is it. Felt safe felt clean that’s about it!"

Reviewed on Jul. 9, 2025

Bedford Plaza Hotel - Boston
Lakeside Inn
Lakeside Inn
2 out of 5
595 North Ave, Wakefield, MA
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Jul 20 to Jul 21
CA $142
CA $159 total
Jul 20 - Jul 21
includes taxes & fees
7.2/10 Good! (2,182 reviews)
"The staff was very helpful and accommodating. The hotel was well kept and comfortable. Over all very good experience !"

Reviewed on Jul. 11, 2025

Lakeside Inn
See all 689 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?
Starting from just CA $705, a package is your passport to low-priced travel. Custom make your Highlands trip by selecting from our wide range of flights, hotels and rental cars.
How do I get a cheap travel package to Highlands?
Booking a Highlands vacation package with Expedia is one of the best ways to save. We offer more than 550 air carriers and 1,000,000 properties spread across the globe. With such a broad range to choose from, you'll have no trouble putting together your perfect getaway.
Where should I stay in Highlands?
With interesting attractions such as University of Massachusetts Lowell and Tsongas Arena in this neighborhood, look for a hotel located near either one. Lowell Memorial Auditorium is another sight in Highlands that pulls the crowds.
How far in advance should I book my Highlands vacation?
It's difficult to pick the perfect time for airfares, but we generally suggest the earlier, the better. Many international flights on Expedia become available up to 12 months in advance. If you're booking last minute, don't fret. Low prices appear from time to time just weeks before departure dates.
What does an Expedia Highlands travel package include?
It comes down to what you're after. If you're traveling alone, you might decide to bundle flights and hotels. Taking the entire family to Highlands? A travel package including rental cars, flights and hotels might suit you better. Expedia gives you the flexibility and freedom to build your own travel package.
What should I know before booking a Highlands travel package?
Whether it's adventure or relaxation you're chasing, a Highlands vacation package lets you organize your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Highlands Expedia vacation package?
Yes --- and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the flexibility to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Highlands vacation package?
Yes, you can. We realize life happens, so we're here to help if you need to make changes to your Highlands vacation package. You may be able to cancel or amend your itinerary at no cost if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if your booking was made more than 24 hours ago. Head to our Customer Service Portal for more information. Also, check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Highlands

Tsongas Arena

4.5/5(3 reviews)

Enjoy a show at Tsongas Arena, a storied theater in Lowell. You can attend a sporting event while in the area.

Tsongas Arena

Things to do

Battle of Lexington and Concord Self-Guided Driving Audio Tour

Battle of Lexington and Concord Self-Guided Driving Audio Tour

CA $18
per traveller
90% of travellers recommend
Battle of Lexington and Concord Self-Guided Driving Audio Tour
See all activities in Lowell
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.