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.
HomeAwhile
Price was CA $1,052, price is now CA $862 per person
CA $862
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
No reviews
This room was very nice for the price. It’s set up like a mini condo with a living room area, stove and near full-size refrigerator in the kitchen area and plenty of storage. It also has a large window in the bedroom area. The bed was also pretty comfortable. All in all it is definitely a great value in a great area with many shopping and dinning options. We will definitely stay here again.
Reviewed on Mar 26, 2026
Portland Harbor Hotel
Downtown Portland
Price was CA $1,851, price is now CA $1,322 per person
CA $1,322
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great.
Reviewed on Mar 24, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $3,261, price is now CA $2,455 per person
CA $2,455
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!
Reviewed on Mar 10, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $1,941, price is now CA $1,519 per person
CA $1,519
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
Property is in an excellent location with so much to see and do (and eat) in walking distance. My room was clean, quiet, and well maintained. Staff interaction was minimal (by design) but the few times I spoke with the concierge on site she was pleasant and accommodating. My only negative comment is regarding the toiletry products. I’m a toilet paper snob and that angel soft just doesn’t cut it. Overall I am beyond satisfied with my stay and would absolutely stay here again.
Reviewed on Mar 22, 2026
Portland Regency Hotel & Spa
Downtown Portland
Price was CA $1,764, price is now CA $1,482 per person
CA $1,482
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,599 reviews)
Excellent breakfast with efficient, friendly staff. Good menu
Reviewed on Mar 27, 2026
Chebeague Island Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Apr 5 to Apr 6
CA $169
CA $187 total
Apr 5 - Apr 6
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
I frequently stay at this property. It is a very clean property with kind and helpful staff and an excellent restaurant and spa. I was locked out of the next door parking garage and Dan (door man?) helped me get my car out. He ran out there in the freezing cold, called the garage mgmt and got me ...
Reviewed on Mar 26, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
The price is CA $119 per night from Apr 13 to Apr 14
CA $119
CA $132 total
Apr 13 - Apr 14
includes taxes & fees
8/10 Very Good! (1,402 reviews)
Great rooms and nice staff
Reviewed on Mar 26, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Apr 5 to Apr 6
CA $158
CA $228 total
Apr 5 - Apr 6
includes taxes & fees
9.2/10 Wonderful! (1,760 reviews)
Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great.
Reviewed on Mar 24, 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.
