Highlands Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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

Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Price was CA $1,063, price is now CA $755 per person
CA $755
per person
Apr 2 - Apr 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,111 reviews)
Clean. Spacious room. Comfortable bed. Great location.

Reviewed on Feb 7, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,305, price is now CA $2,095 per person
CA $2,095
per person
Apr 28 - May 1
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,384, price is now CA $1,736 per person
CA $1,736
per person
May 6 - May 9
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you

Reviewed on Feb 3, 2026

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave

2.5 out of 5
South End
Price was CA $1,825, price is now CA $1,413 per person
CA $1,413
per person
May 7 - May 12
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
7.8/10 Good! (66 reviews)
Biggest problem was that I never got the email with the access codes after checking in online. The place has no personnel on site, so I couldn't get in when it was really cold outside. Had to call customer service, where it was resolved. Within a few minutes. I could hear pretty much everything that went on in the room next door, and even when people just went up and down the stairs in front of my room, I could hear everything. The view out of the window is pretty terrible. It's basically just looking into other peoples' pretty wild back yards. Perhaps in the summer it looks a bit nicer.

Reviewed on Dec 6, 2025

Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
Final resting place of Jack Kerouac ❤️

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

Hyatt Place Boston/Medford

Hyatt Place Boston/Medford

3 out of 5
116 Riverside Ave Medford MA
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Mar 1 to Mar 2
CA $149
CA $167 total
Mar 1 - Mar 2
includes taxes & fees
8.2/10 Very Good! (1,658 reviews)
Overall, things were fine. The closet door in our room was broken and couldn’t move. The heat wasn’t on in the gym and it was 55°. Breakfast was mediocre at best. Not even any real bacon and potatoes were undercooked. Gym equipment was fine. Staff were friendly. Room was quiet. Elevators were ...

Reviewed on Feb 6, 2026

Hyatt Place Boston/Medford
Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham

2.5 out of 5
135 2nd Ave Waltham MA
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Feb 21 to Feb 22
CA $121
CA $136 total
Feb 21 - Feb 22
includes taxes & fees
9.2/10 Wonderful! (1,636 reviews)
Nice rooms and great breakfast.

Reviewed on Feb 4, 2026

Hampton Inn & Suites Boston/Waltham
Best Western Plus Waltham Boston

Best Western Plus Waltham Boston

3 out of 5
380 Winter Street Waltham MA
Fully refundableReserve now, pay when you stay
The price is CA $97 per night from Feb 16 to Feb 17
CA $97
CA $108 total
Feb 16 - Feb 17
includes taxes & fees
8.2/10 Very Good! (1,154 reviews)
The room was comfortable and warm on a frigid night. The staff were all friendly and helpful and the breakfast was excellent.

Reviewed on Feb 10, 2026

Best Western Plus Waltham Boston
See all 763 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 $755, 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 $20
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.