Peaks Island Vacation Packages
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Your Peaks Island Vacation
With plenty of highlights as well as some hidden gems, this city is best experienced with a Peaks Island vacation package. Check out places to stay in Parkside, which is great for festivals, markets and walking. If taking in sights is on the agenda during your trip to Peaks Island, look around major attractions like Sand Beach, Fifth Maine Museum and Little Diamond Island. Check out Expedia's wide range of travel options and book your ideal vacation to Peaks Island today.
Top Peaks Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Price was CA $1,882, price is now CA $1,369 per person
CA $1,369
per person
May 16 - May 21
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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 $2,255, price is now CA $1,782 per person
CA $1,782
per person
May 16 - May 21
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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
Portland Regency Hotel & Spa
Downtown Portland
Price was CA $1,717, price is now CA $1,372 per person
CA $1,372
per person
May 16 - May 21
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,599 reviews)
Our stay at Portland Regency Hotel and Spa was amazing. The staff greeted us with such warmth. Our room was exceptional and the food was superb.
Reviewed on Mar 22, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $2,038, price is now CA $1,629 per person
CA $1,629
per person
May 16 - May 21
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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
The Weldon Hotel
Downtown Portland
Price was CA $2,170, price is now CA $1,788 per person
CA $1,788
per person
May 16 - May 21
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (94 reviews)
The hotel is in an ideal location in downtown Portland. The staff is so kind and very accommodating! The stay was beyond comfortable and is the place we will stay every time we return to Portland!
Reviewed on Mar 23, 2026
Peaks Island Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Apr 13 to Apr 14
CA $135
CA $149 total
Apr 13 - Apr 14
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
The staff was very helpful. Breakfast was included. Full service, not continental. Really good food. Parking was validated. No surprises on put bill. Definitely recommended.
Reviewed on Mar 22, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
The price is CA $106 per night from Apr 13 to Apr 14
CA $106
CA $117 total
Apr 13 - Apr 14
includes taxes & fees
8/10 Very Good! (1,404 reviews)
Clean room , nice pool area and quiet ,will say that the beds are kinda uncomfortable but if you’re there for a night it’s not too bad ! I’d come back again.
Reviewed on Mar 22, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Apr 5 to Apr 6
CA $156
CA $225 total
Apr 5 - Apr 6
includes taxes & fees
9.2/10 Wonderful! (1,774 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.
What to do in Peaks Island
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 $23
per traveller
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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.
