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.
Portland Regency Hotel & Spa
Downtown Portland
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,368 reviews)
The hotel is lovely and we had stayed there before and loved it. This time our room was smaller and more expensive. With the added price of parking and the smaller sized room, I was disappointed as the last time our room was larger. It was as if they took a room that was meant to have one king sized bed and put two queen sized beds in the room. Also the bathrooms could use a refresh.
Reviewed on Aug. 13, 2025
Kennebunkport Captains Collection
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (600 reviews)
The breakfast each more was varied and delicious. There are bikes on the property which are great to ride around town
Reviewed on Jul. 29, 2025
Quality Inn
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
7.8/10 Good! (625 reviews)
Very nice hotel. Beds are a bit outdated and hard, but clean. Strong air freshner in hallways so beware if you have asthma or fragrance allergy.
Reviewed on Aug. 14, 2025
USA Inn
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
7.8/10 Good! (665 reviews)
Our first time staying at this property. Check-in was super easy. Staff was very friendly.
Parking was easy.
Property is older so don't expect anything fancy. They do offer 3 k-cups in your room; I thought that was nice. Anything additional is $1.00 per cup.
The reason for my 4 stars is how loud the people were above us. Oh, my! Floors/walls are thin. We could hear everything. 😞
I would stay here again, I would just ask for a room on top floor. 😄
Reviewed on Aug. 14, 2025
Great Diamond Island Hotel Deals
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 $160 per night from Aug 24 to Aug 25
CA $160
CA $174 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,159 reviews)
"Great value and location."
Reviewed on Aug. 12, 2025
Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Aug 20 to Aug 21
CA $209
CA $232 total
Aug 20 - Aug 21
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"Convenient, good location"
Reviewed on Aug. 14, 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 $134 per night from Aug 24 to Aug 25
CA $134
CA $146 total
Aug 24 - Aug 25
includes taxes & fees
7.4/10 Good! (142 reviews)
"No comment"
Reviewed on Aug. 13, 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
4.5/5(5 reviews)
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
5/5(5 reviews)
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
Sunset Lighthouse Cruise Tour from Casco Bay
CA $77
per adult
90% of travellers recommend
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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.