Great Diamond Island Vacation Packages
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Top Great Diamond Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Weldon Hotel
Downtown Portland
Price was CA $1,690, price is now CA $1,251 per person
CA $1,251
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
9.8/10 Exceptional! (71 reviews)
This is probably the cleanest, most beautiful hotel for the money we’ve ever stayed in. The nightly rate was comparable to the other hotel rooms in town, but here you get a huge spacious apartment! All new, chic, and very comfortable. Easy to walk to Wharf St. and the dining and shopping area too! The manager was very responsive, friendly and accommodating as well! This place is a gem!
Reviewed on Aug. 26, 2025
The Docent's Collection
Downtown Portland
Price was CA $2,414, price is now CA $1,826 per person
CA $1,826
per person
Oct 9 - Oct 12
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (226 reviews)
Very modern and new condition. Digital key worked pretty well and convenient. Lots of good restaurants within walking distance. We enjoyed our stay.
Reviewed on Aug. 25, 2025
Hampton Inn Portland Downtown - Waterfront
Downtown Portland
Price was CA $1,935, price is now CA $1,572 per person
CA $1,572
per person
Oct 9 - Oct 12
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (1,004 reviews)
The staff was remarkable, friendly, ready to help with any need.
Reviewed on Aug. 27, 2025
Portland Harbor Hotel
Downtown Portland
Price was CA $2,304, price is now CA $1,898 per person
CA $1,898
per person
Oct 9 - Oct 12
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,545 reviews)
Great location. You can walk famous restaurants and it’s pretty safe. The room was clean and the staff were very friendly.
Reviewed on Aug. 25, 2025
Canopy by Hilton Portland Waterfront
Downtown Portland
Price was CA $2,243, price is now CA $1,852 per person
CA $1,852
per person
Oct 9 - Oct 12
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,009 reviews)
Near the waterfront. Great location in Old Port. We had a wonderful 2 night stay
Reviewed on Aug. 26, 2025
Great Diamond Island Hotel Deals
Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Sep 2 to Sep 3
CA $210
CA $233 total
Sep 2 - Sep 3
includes taxes & fees
Days Inn by Wyndham Airport/Maine Mall
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Aug 28 to Aug 29
CA $161
CA $175 total
Aug 28 - Aug 29
includes taxes & fees
7.8/10 Good! (1,242 reviews)
"This Days Inn is a great place to stay."
Reviewed on Aug. 24, 2025
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 $125 per night from Sep 15 to Sep 16
CA $125
CA $136 total
Sep 15 - Sep 16
includes taxes & fees
7.2/10 Good! (182 reviews)
Tammy
"The room in general was clean 👌"
Reviewed on Aug. 24, 2025
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.
Discover the most popular places to visit in Great Diamond Island
State Theatre
The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.
Portland Museum of Art
Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.
East End Beach
Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.
What to do in Great Diamond Island
Afternoon Windjammer Cruise Along the Coast of Portland Maine
CA $92
per adult
Portland: Sightseeing Cruise to Portland Head Light
CA $56
per adult
98% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
CA $81
per adult
90% of travellers recommend
Frequently asked questions
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General
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.