
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 Docent's Collection
Downtown Portland
per person
Oct 23 - Oct 26
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (219 reviews)
Property is modern and clean and a great choice if staying more than one night. The 5:00 check in time is inconvenient and the additional rates for early check in are ridiculous. Our room was ready early even though the information given before check in stated early check in was not available, so we appreciated that. Bed was okay comfort-wise, but the pillows are awful.
The biggest gripe I had was being woken by a very loud family with screaming kids well before 7:30 am on a day we looked forward to sleeping in. If this matters to you, the walls and floors are not very soundproof. This was a very unpleasant way to start the second day of a two-day trip. On a positive note, the staff was available via text and responded to our questions quickly and professionally. One suggestion-an exterior sign. The loft was hard to find, with only small signage on the entry doors which is not easily visible from the street. Overall we were happy and would stay again.
Reviewed on Aug. 11, 2025


Cliff House Maine
per person
Sep 23 - Sep 30
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,005 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!
Reviewed on Aug. 9, 2025


Portland Harbor Hotel
Downtown Portland
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
The central garden area for drinks and meals was a real positive. We had pre dinner drinks and breakfast coffee there.
Reviewed on Aug. 12, 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

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! (132 reviews)
"Everything from Germaine Inn South Portland is pretty good rooms, facilities, pool etc.. I only whish they provide breakfast until 10AM instead of 9AM."
Reviewed on Aug. 11, 2025

Ramada Plaza by Wyndham Portland
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from Sep 1 to Sep 2
CA $183
CA $202 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (1,046 reviews)
"Motel was great the employees were awesome The only thing that was a concern was our patio it was not swept and did not have chairs to sit on"
Reviewed on Aug. 11, 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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