Highland Vacation Packages
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Top Holiday Package Deals in Highland
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
Price was CA $1,931, price is now CA $816 per person
CA $816
per person
Dec 18 - Dec 23
found 15 hours 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
Fairmont Copley Plaza, Boston
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 1 day 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
Where to stay in Highland
Find the best Highland areas and neighborhoods for the activities you enjoy most. Learn more about Highland
Willard Beach
2 out of top 10 points of interest in this area
If you're looking for some top things to see and do in Willard Beach and surrounding area, you can visit Willard Beach and Spring Point Ledge Lighthouse.
Highland Hotel Deals
Best Western Merry Manor Inn
700 Main St South Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Nov 23 to Nov 24
CA $172
CA $188 total
Nov 23 - Nov 24
includes taxes & fees
9/10 Wonderful! (1,262 reviews)
"The rooms were clean and we enjoyed the hot tub and outdoor sitting area with a fire. The outdoor pool was warm and guests were swimming in it which was in late October. I used the exercise room during our stay which was great. Breakfast had a good amount of choices. We enjoyed our stay and the amenities ..."
Reviewed on Oct 28, 2026
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Nov 22 to Nov 23
CA $151
CA $167 total
Nov 22 - Nov 23
includes taxes & fees
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
The price is CA $113 per night from Nov 5 to Nov 6
CA $113
CA $125 total
Nov 5 - Nov 6
includes taxes & fees
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.
Things to do
Harbor Lights and Sights Cruise
CA $86
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $109
per adult
92% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
CA $83
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.