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 Westin Portland Harborview
Downtown Portland
per person
Aug 31 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (1,005 reviews)
The hotel was very nice. Our room was elegant and quiet. The hotel lobby and front entrance are not ADA friendly. Lots of stairs and no ramps when you first enter the building. When we exited off of the highway and into Portland there were a lot of homeless people and graffiti on the buildings. Being from Chicago this did not make us very comfortable as "tagging" i.e. graffiti has a purpose and meaning. We loved the hotel but arriving later in the evening and being tired we did not feel safe going beyond the hotel to eat dinner. Therefore, we went to bed hungry because everything in the hotel was already closed.
Reviewed on Jul. 19, 2025
The McKernan Inn
Save 100% on your flight
per person
Aug 31 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (31 reviews)
The light switch at the door turns the TV on and off, which isn’t very convenient. The shower knob that changes the water from the spout to the showerhead kept falling out. The drop ceilings are gross and have black mold on them. The view is lovely from the windows.
Reviewed on Jul. 21, 2025
Blind Tiger Portland - Danforth Street.
West End
Save 100% on your flight
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.6/10 Exceptional! (147 reviews)
Small bathroom. No safe. No storage space. Everything else was above average.
Reviewed on Jul. 16, 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 $173 per night from Jul 24 to Jul 25
CA $173
CA $189 total
Jul 24 - Jul 25
includes taxes & fees
7.8/10 Good! (1,051 reviews)
"Convenient"
Reviewed on Jul. 21, 2025
Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Jul 27 to Jul 28
CA $208
CA $230 total
Jul 27 - Jul 28
includes taxes & fees
7.8/10 Good! (1,013 reviews)
"."
Reviewed on Jul. 19, 2025
Comfort Inn Airport
90 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Jul 27 to Jul 28
CA $171
CA $187 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very Good! (1,407 reviews)
"Great staff. Breakfast is very well done."
Reviewed on Jul. 18, 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 $91
per adult
Sunset Lighthouse Cruise Tour from Casco Bay
CA $77
per adult
90% of travellers recommend
Portland: Sightseeing Cruise to Portland Head Light
CA $49
per adult
98% of travellers recommend
Frequently asked questions
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