Hillside Vacation Packages
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Top Hillside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Saco Bay Hotel
Price was CA $1,303, price is now CA $1,093 per person
CA $1,093
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
7.6/10 Good! (1,051 reviews)
We just had a night stay there during a journey but it was comfortable and what we needed
Reviewed on May 7, 2026
The Weldon Hotel
Downtown Portland
Price was CA $2,283, price is now CA $1,858 per person
CA $1,858
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless,
Great location. Would stay here again
Reviewed on Apr 23, 2026
1802 House Bed and Breakfast
Price was CA $1,622, price is now CA $1,347 per person
CA $1,347
per person
Jun 18 - Jun 20
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.6/10 Exceptional! (104 reviews)
Great place to stay for a getaway. Breakfast is outstanding, hostess and her husband prepare fresh ingredients with three tasty courses.
Rooms are well decorated, clean, bright and comfortable. We stayed there in 2001 and again in 2025. Our favorite in Kennebunk Port.
Reviewed on Oct 28, 2025
Ogunquit River Inn & Suites
Price was CA $1,336, price is now CA $1,134 per person
CA $1,134
per person
Jun 18 - Jun 20
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9/10 Wonderful! (1,000 reviews)
The front desk was incredibly nice. They moved us closer to our family in another room without being asked. It was very appreciated, thank you.
Reviewed on May 3, 2026
Portland Harbor Hotel
Downtown Portland
Price was CA $1,700, price is now CA $1,453 per person
CA $1,453
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,753 reviews)
Really enjoyed our stay. Staff was great as well!
Reviewed on May 8, 2026
Hillside Hotel Deals
Dormir
965 Roosevelt Trail Windham ME
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from May 26 to May 27
CA $222
CA $242 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Return stay! Excellent service and amenities!
Reviewed on May 8, 2026
Oxford Casino Hotel
777 Casino Way Oxford ME
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Jun 8 to Jun 9
CA $175
CA $191 total
Jun 8 - Jun 9
includes taxes & fees
Hampton Inn Oxford
151 Main St Oxford ME
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from May 19 to May 20
CA $154
CA $168 total
May 19 - May 20
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Our stay was pleasant. Staff was helpful. Breakfast was one of the best of all the places we've been.
Reviewed on Apr 26, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
