Highlands Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
Bluebird Dennisport

Bluebird Dennisport

3 out of 5
Price was CA $1,865, price is now CA $1,208 per person
CA $1,208
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very good! (223 reviews)
This was an amazing location! The entire staff was nice and helpful. It is just a 10 min walk to the beach and close to many great places to eat. I can’t wait to come back!!

Reviewed on Jul 9, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Price was CA $4,273, price is now CA $2,651 per person
CA $2,651
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (722 reviews)
Everything was amazing, my room the A/C wasn’t cooling properly but they fixed it quick,

Reviewed on Jul 10, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,469, price is now CA $1,614 per person
CA $1,614
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great 👍

Reviewed on Jul 11, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $4,510, price is now CA $2,967 per person
CA $2,967
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (720 reviews)
Muy caro para lo que se recibe……..Aunque la habitación este literalmente sobre la playa. La cerradura de la habitación no funcionaba correctamente. Y la luz en la manana se entra por las cortinas

Reviewed on Jul 11, 2026

Studio Allston Hotel

Studio Allston Hotel

4 out of 5
Brighton
Price was CA $2,140, price is now CA $1,474 per person
CA $1,474
per person
Sep 11 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
8.6/10 Excellent! (1,272 reviews)
Great hotel Super friendly staff

Reviewed on Jul 10, 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

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 $140 per night from Aug 9 to Aug 10
CA $140
CA $157 total
Aug 9 - Aug 10
includes taxes & fees
8.4/10 Very good! (2,798 reviews)
"staff very kind and help for"

Reviewed on Jul 10, 2026

Four Points by Sheraton Boston Newton
Lakeside Inn

Lakeside Inn

2 out of 5
595 North Ave Wakefield MA
Fully refundable
The price is CA $121 per night from Jul 15 to Jul 16
CA $121
CA $135 total
Jul 15 - Jul 16
includes taxes & fees
7.6/10 Good! (2,396 reviews)
"Perfect setup will be back"

Reviewed on Jul 10, 2026

Lakeside Inn
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 $98 per night from Jul 13 to Jul 14
CA $98
CA $110 total
Jul 13 - Jul 14
includes taxes & fees
7/10 Good! (1,020 reviews)
"Tout est nul à parts staff"

Reviewed on Jul 10, 2026

Bedford Plaza Hotel - Boston
See all 749 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 $1,208, 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

Cambodia Town

10.0/10 (1 review)
You can do some window-shopping at Cambodia Town during your stay in 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.