Highlands Vacation Packages

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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $1,417, price is now CA $948 per person
CA $948
per person
May 9 - May 12
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Boston (BOS)
8.8/10 Excellent! (1,426 reviews)
The location is excellent, very short walk to TD Garden arena, restaurants, and bars. The room was comfortable, and clean. The work out room was not huge but had a peleton and treadmill, bench, and plenty of weights (up to 35 lb) for a solid workout. I would recommend and stay again.

Reviewed on Apr 8, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,243, price is now CA $1,267 per person
CA $1,267
per person
May 16 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
From the moment we arrived we knew we made the right decision. The property is beautiful and the staff are professional and friendly. We were very pleased with our room and the great view of Boston Harbor. Two minor issues were the water spot on the bathroom sinks were too short for the size of the sink, making it hard to use without making a mess (wide designs such things and knows). The other minor item was the quality of the toilet tissue, for a hotel of this caliber, the need to spend a little more there. I must say that these were minor issues considering how amazing this property is. We went to the Dark Bar twice and loved it, had breakfast in the hotel restaurant and couldn’t have been more pleased and also had room service dinner one night and were very impressed. I would highly recommend this property!

Reviewed on Apr 6, 2026

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was CA $2,529, price is now CA $1,545 per person
CA $1,545
per person
May 25 - May 29
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
10/10 Exceptional! (18 reviews)
We absolutely loved our stay at this new hotel. My family and I kept saying what a really nice hotel and the staff was great as well. The food at Ama (we ate breakfast) was delicious. The property is beautiful. Can’t wait to stay again.

Reviewed on Apr 5, 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was CA $2,994, price is now CA $1,979 per person
CA $1,979
per person
May 25 - May 29
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (535 reviews)
Loved all of it. Thank you to Jaclyn for a wonderful stay!

Reviewed on Apr 7, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,283, price is now CA $1,520 per person
CA $1,520
per person
May 25 - May 29
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (253 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

Where to stay in Highlands

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

South Lowell

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

Find hotels in South Lowell

Highlands Hotel Deals

Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
320 Washington Street Newton MA
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from May 3 to May 4
CA $128
CA $143 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (2,848 reviews)
Friendly staff

Reviewed on Apr 9, 2026

Four Points by Sheraton Boston Newton
Hilton Boston/Woburn

Hilton Boston/Woburn

3.5 out of 5
2 Forbes Rd. Woburn MA
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from May 1 to May 2
CA $181
CA $202 total
May 1 - May 2
includes taxes & fees
8.6/10 Excellent! (1,272 reviews)
Hostess check in Staff was rude unless you were wearing an airline uniform. Waitstaff was rude at breakfast. Door dash isn’t allowed to deliver to the rooms but half the time the elevators didn’t work . Parking was almost impossible to find.

Reviewed on Apr 9, 2026

Hilton Boston/Woburn
Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham

3 out of 5
135 2nd Ave Waltham MA
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from May 3 to May 4
CA $169
CA $189 total
May 3 - May 4
includes taxes & fees
9.4/10 Exceptional! (1,708 reviews)
Great room.

Reviewed on Apr 9, 2026

Hampton Inn & Suites Boston/Waltham
See all 769 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.
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Frequently asked questions

How much does a Highlands vacation package cost?
Starting from just CA $948, 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.