
Cliff Island Vacation Packages
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Top Cliff Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.


Blind Tiger Portland - Danforth Street.
West End
Price was CA $3,064, price is now CA $2,615 per person
CA $2,615
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Portland (PWM)
9.6/10 Exceptional! (150 reviews)
Small bathroom. No safe. No storage space. Everything else was above average.
Reviewed on Jul. 16, 2025

Longfellow Hotel
Parkside
Price was CA $2,314, price is now CA $2,026 per person
CA $2,026
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Portland (PWM)
9.6/10 Exceptional! (112 reviews)
Superb design. Rooms are elegant, comfortable, convenient. This is an outstanding hotel
Reviewed on Aug. 25, 2025

Dormir
Price was CA $1,957, price is now CA $1,775 per person
CA $1,775
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Portland (PWM)
8.8/10 Excellent! (1,000 reviews)
For the price I would have liked to have my bed made and fresh towels replaced every day. Breakfast was really good but ditch those fake eggs. Over all it was great. Would stay there again.
Reviewed on Aug. 17, 2025

Inn By The Sea
Price was CA $3,040, price is now CA $2,758 per person
CA $2,758
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Portland (PWM)
9.4/10 Exceptional! (279 reviews)
We chose Inn by the Sea because it was advertised as a “pet-friendly” property with beach access for pets, which was a key factor in our decision. Unfortunately, our experience didn’t quite align with those expectations.
We arrived on a Sunday around noon and, as expected, our room wasn’t ready (check-in is at 4:00pm). However, unlike many hotels, we were not offered anything while we waited — no welcome drink, light refreshment, or even an early check-in estimate — despite having to wait the full four hours.
Once we checked in, we were told our assigned room was not pet-friendly, and we would be charged for any accidents — despite booking under the premise that this was a pet-friendly stay. Additionally, the restaurant only allows pets in the outdoor seating area, and the pool area is not pet-friendly at all. So while the hotel does accommodate pets in some areas, it’s misleading to call it fully pet-friendly when the main guest amenities are off-limits.
That said, the property is beautiful and most of the staff were friendly and professional, which we appreciated. But overall, if you’re traveling with a pet and hoping for a truly integrated experience, this may not be the best fit.
Reviewed on Aug. 18, 2025
Cliff Island Hotel Deals

Germaine Inn South Portland
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is CA $117 per night from Oct 5 to Oct 6
CA $117
CA $128 total
Oct 5 - Oct 6
includes taxes & fees

Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Sep 11 to Sep 12
CA $175
CA $193 total
Sep 11 - Sep 12
includes taxes & fees

Ramada Plaza by Wyndham Portland
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Sep 7 to Sep 8
CA $193
CA $214 total
Sep 7 - Sep 8
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.
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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.