Highlands Vacation Packages

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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,931, price is now CA $816 per person
CA $816
per person
Dec 18 - Dec 23
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was CA $2,512, price is now CA $1,380 per person
CA $1,380
per person
Dec 2 - Dec 8
found 22 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)
They charged me a $250 pet fee for one night. Be warned that they will rip you off.

Reviewed on Oct 28, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was CA $1,647, price is now CA $1,034 per person
CA $1,034
per person
Dec 11 - Dec 13
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
Excellent as always.

Reviewed on Oct 27, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was CA $2,646, price is now CA $1,736 per person
CA $1,736
per person
Dec 2 - Dec 8
found 22 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (1,354 reviews)
The Fairmont Gold level is the best I’ve ever experienced. From the way on line booking to the upgrade section, it was seamless. At check in, Kevin, got my room ready even though I was 6 hours early. Later that day, Kadija was accommodating to my request without any hesitation.

Reviewed on Oct 27, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Lexington Green Historic District
Save 100% on your flight
Price was CA $1,638, price is now CA $1,125 per person
CA $1,125
per person
Dec 4 - Dec 7
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (268 reviews)
Gorgeous and cosy with great breakfast

Reviewed on Oct 22, 2026

Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
A gravestone with the inscription "Jack Kerouac" and the quote "The Road is Life".

South Lowell

1 out of top 10 points of interest in this area

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

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 $130 per night from Nov 22 to Nov 23
CA $130
CA $145 total
Nov 22 - Nov 23
includes taxes & fees
8.4/10 Very good! (2,678 reviews)
"Property is located above the Mass Pike so lower floors can be noisy. However it is a terrific property with updated amenities."

Reviewed on Oct 28, 2026

Four Points by Sheraton Boston Newton
Bedford Plaza Hotel - Boston

Bedford Plaza Hotel - Boston

3 out of 5
340 Great Road Bedford MA
Fully refundableReserve now, pay when you stay
The price is CA $100 per night from Nov 1 to Nov 2
CA $100
CA $112 total
Nov 1 - Nov 2
includes taxes & fees
6.6/10 (1,356 reviews)
"It was ok. ✅ quite. For the money I paid. It was ok. ✅."

Reviewed on Oct 28, 2026

Bedford Plaza Hotel - Boston
Methuen Inn and Conference Center

Methuen Inn and Conference Center

2.5 out of 5
159 Pelham Street Methuen MA
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Nov 5 to Nov 6
CA $128
CA $143 total
Nov 5 - Nov 6
includes taxes & fees
Methuen Inn and Conference Center
See all 757 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
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Family Vacations
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Frequently asked questions

How much does a Highlands vacation package cost?
Starting from just CA $816, 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.

Stay near popular Highlands attractions

Taffeta Music Hall

You can get tickets for a performance at Taffeta Music Hall on your trip to Lowell.
See properties

Things to do

Battle of Lexington and Concord Self-Guided Driving Audio Tour

Battle of Lexington and Concord Self-Guided Driving Audio Tour

CA $21
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.