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.
Cliff House Maine
Bald Head
Price was CA $4,313, price is now CA $2,919 per person
CA $2,919
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.4/10 Exceptional! (1,007 reviews)
Gorgeous room in a gorgeous setting. Norman the lead bartender is a treasure. Hector was great as well. Everything was outstanding.
Reviewed on Mar 25, 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
Peaks Island Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Apr 15 to Apr 16
CA $178
CA $197 total
Apr 15 - Apr 16
includes taxes & fees
8.8/10 Excellent! (1,001 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! (1,401 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 $157 per night from Apr 5 to Apr 6
CA $157
CA $227 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.
