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

Dorchester

Save 100% on your flight

CA $964

per person

Dec 24 - Dec 27

found 9 hours ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

8.4/10 Very good! (190 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

Boston Harbor Hotel

North End

Save 100% on your flight

CA $1,366

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Boston (BOS)

9.8/10 Exceptional! (1,008 reviews)

Raffles Boston

Back Bay

Save 100% on your flight

CA $1,356

per person

Dec 25 - Dec 28

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Boston (BOS)

9.6/10 Exceptional! (332 reviews)

Four Seasons Hotel Boston

Bay Village

Save 100% on your flight

CA $1,851

per person

Dec 25 - Dec 28

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Boston (BOS)

9.4/10 Exceptional! (487 reviews)

For the most high end hotel in Boston, lacked updated amenities that other newer hotels have. Rooms were severely dated.

Reviewed on Oct 20, 2026

Mandarin Oriental, Boston

Back Bay

Save 100% on your flight

CA $1,830

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTZ) to Boston (BOS)

9.4/10 Exceptional! (458 reviews)

Where to stay in Highlands

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

A river running through a city with multiple buildings, roads, and a bridge.

Downtown Manchester

6 out of top 10 points of interest in this area

If you're spending some time in Downtown Manchester, City Hall Plaza and Millyard Museum are top sights worth seeing.

Lower South Willow

1 out of top 10 points of interest in this area

While Lower South Willow isn't home to many top sights, Mall of New Hampshire and Filotimo Casino are some notable places to visit nearby.

Kalivas Union

While Kalivas Union isn't home to many top sights, Southern New Hampshire University Arena and Northeast Delta Dental Stadium are some notable places to visit nearby.

A river with a bridge, a red brick building, and a street sign indicating 'The Mill Yard'.

South End

While South End might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Mall of New Hampshire and Filotimo Casino.

A cityscape with a prominent red brick building, a church spire, and a parking lot filled with cars.

North End

If you're spending some time in North End, Zimmerman House and Livingston Park are top sights worth seeing.

Highlands Hotel Deals

Marvelous 3-bedroom townhome with Heated floor Manchester

Manchester NH

CA $277

CA $519 total

Oct 29 - Oct 30

includes taxes & fees

9/10 Wonderful! (7 reviews)

"We were very appreciative of being able to check in a little early. However, the check-in instructions and information could have been much clearer. We rented the full 3-bedroom house, but each bedroom had a digital lock requiring a code. We were not given all of the codes initially and had to ask ..."

Reviewed on Oct 5, 2026

Park View Inn - Salem

109 S Broadway Salem NH

Fully refundableReserve now, pay when you stay

CA $113

CA $123 total

Nov 18 - Nov 19

includes taxes & fees

Comfort Inn Manchester Airport

298 Queen City Ave Manchester NH

Fully refundable

CA $146

CA $158 total

Nov 9 - Nov 10

includes taxes & fees

8.2/10 Very good! (1,012 reviews)

"The room was not Very well cleaned, there were dusty spots and smear on some areas. The linen on the bed seemed used."

Reviewed on Oct 20, 2026

See all 312 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.