Chebeague Island Vacation Packages
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Your Chebeague Island Vacation
Book a Chebeague Island vacation package that has only the things you need and nothing you don't. Good for festivals, markets and walking, consider staying in the neighborhood of Parkside. If a sightseeing tour is part of the program during your trip to Chebeague Island, check out major attractions like Eagle Island, Little John Island Preserve and Sturdivant Island. That dream Chebeague Island vacation is a couple of clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored to suit your style.
Top Chebeague Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Saco Bay Hotel
Price was CA $1,432, price is now CA $1,210 per person
CA $1,210
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
7.6/10 Good! (1,051 reviews)
The internet was not secure
The room did not have room darkening drapes.
Breakfast was good.
TV not usefall no NBC,ABC,CBS channel and very few other channels to watch except old out of date programming.
Reviewed on May 11, 2026
Portland Harbor Hotel
Downtown Portland
Price was CA $3,153, price is now CA $2,476 per person
CA $2,476
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,753 reviews)
Hotel is beautiful but rooms are small! Tight for 3 people. The parking is expensive and only option is valet. There’s always a long wait to get your car, they don’t go in order and are rude. The “free” snacks on the various floors were nothing special. Instead of sparkling water, have regular available. Also some real snacks not just granola and mints.
Otherwise it was beautiful!
Reviewed on May 13, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $2,442, price is now CA $2,049 per person
CA $2,049
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (304 reviews)
It’s a good place to stay when rates aren’t sky high. Paying over $300 a night plus $60 to self park for Portland is ridiculous.
Clean rooms, quiet. The digital key system is a hassle to get working if you’re not using Safari on iOS.
Reviewed on May 13, 2026
Canopy by Hilton Portland Waterfront
Downtown Portland
Price was CA $2,671, price is now CA $2,263 per person
CA $2,263
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
The breakfast on Mother’s Day was amazing. We loved the Luna rooftop. The staff and bartenders were top notch. The hotel was very well kept. Definitely will be back.
Reviewed on May 11, 2026
The Weldon Hotel
Downtown Portland
Price was CA $2,989, price is now CA $2,660 per person
CA $2,660
per person
Jun 17 - Jun 21
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
Chebeague Island Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $254 per night from May 25 to May 26
CA $254
CA $333 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (1,769 reviews)
Hotel is beautiful but rooms are small! Tight for 3 people. The parking is expensive and only option is valet. There’s always a long wait to get your car, they don’t go in order and are rude. The “free” snacks on the various floors were nothing special. Instead of sparkling water, have regular available. ...
Reviewed on May 13, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $224 per night from May 27 to May 28
CA $224
CA $248 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (1,651 reviews)
A hotel has control over cleanliness, upkeep, and service. This hotel ranks very poorly in service. Not a single smile from any staff at check-in, check-out, or requests. They advertise pickup from the airport is available but after a call before flight, after landing, and then 3 more calls after ...
Reviewed on May 12, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $228 per night from May 26 to May 27
CA $228
CA $290 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,217 reviews)
Best customer service I have ever received.
Reviewed on May 13, 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.
