Highland Vacation Packages
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Top Holiday Package Deals in Highland
Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston
Price was CA $2,024, price is now CA $1,255 per person
CA $1,255
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (254 reviews)
Excellent experience- clean and very helpful staff
Reviewed on Mar 9, 2026
The Langham, Boston
Downtown Boston
Price was CA $3,051, price is now CA $1,650 per person
CA $1,650
per person
Jun 27 - Jun 30
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
The staff were so kind and let us check in early. They constantly asked how we were enjoying the stay and if there was anything that we needed. The property was clean and super cute!
Reviewed on Apr 13, 2026
Eurostars The Boxer
West End
Price was CA $2,765, price is now CA $1,798 per person
CA $1,798
per person
Jun 18 - Jun 22
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,435 reviews)
Clean room and good staff. Room is a bit outdated
Reviewed on Apr 15, 2026
The Ritz-Carlton, Boston
Downtown Boston
Price was CA $4,894, price is now CA $3,218 per person
CA $3,218
per person
Jun 27 - Jun 30
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (449 reviews)
Club level is well worth it. The service was wonderful
Reviewed on Apr 16, 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 $140 per night from Apr 30 to May 1
CA $140
CA $152 total
Apr 30 - May 1
includes taxes & fees
9/10 Wonderful! (1,031 reviews)
Room was clean, lobby very nice with Coffee 24/7, cold drinks to purchase & small conveniences. Tons of kids, great place for parents. Not so great for adults as hot tub was full of kids all the time. An adults only hot tub hour would be nice! Breakfast was a zoo. Food was fine.
Reviewed on Apr 17, 2026
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Apr 20 to Apr 21
CA $204
CA $226 total
Apr 20 - Apr 21
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
A fine location with nice rooms and helpful staff. The bar on the 15th floor has a nice view of the harbor and pretty good draft beer. Don't order food - or at least the tots as the serving size is meager and quality very low. Not to mention the high cost. Like many cities, Portland does struggle ...
Reviewed on Apr 17, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Apr 26 to Apr 27
CA $167
CA $236 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (1,757 reviews)
The location was very good because you can walk to everything you need in the area. The only thing we didn’t like was the automatic $35 fee you can use toward meals etc in their restaurant, but if you don’t use it you get charged the fee anyway. We felt like it was a way to force us to eat in their ...
Reviewed on Apr 17, 2026
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.
Discover the most popular places to visit in Highland
Maine Mall
4/5(65 reviews)
You can do some window-shopping at Maine Mall during your visit to South Portland. Experience the area's entertainment choices and great live music.
Things to do
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
CA $14
per traveller
Ultimate Portland Self-Guided Driving GPS Audio Tour
CA $23
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
CA $21
per traveller
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.