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
Price was CA $1,928, price is now CA $1,713 per person
CA $1,713
per person
Dec 29 - Jan 3
found 1 hour ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9.4/10 Exceptional! (1,780 reviews)
Staff was very nice. Clean room with cool balcony.
Reviewed on Nov 7, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $2,497, price is now CA $2,165 per person
CA $2,165
per person
Dec 29 - Jan 3
found 1 hour ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9.6/10 Exceptional! (419 reviews)
Not very much parking and you have to schedule it in advance. Expedia didn't warn. It could be a disaster if you don't plan for it and rent a car.
Reviewed on Nov 7, 2026
Great Diamond Island Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Dec 6 to Dec 7
CA $143
CA $158 total
Dec 6 - Dec 7
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"My visit was great! The hotel was quiet and clean and all the staff was so kind and helpful!"
Reviewed on Nov 7, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
The price is CA $114 per night from Nov 15 to Nov 16
CA $114
CA $126 total
Nov 15 - Nov 16
includes taxes & fees
8.2/10 Very good! (1,856 reviews)
"Decent hotel for the price of a room. Quiet and close enough to where we were going for the evening."
Reviewed on Nov 7, 2026
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Nov 12 to Nov 13
CA $129
CA $142 total
Nov 12 - Nov 13
includes taxes & fees
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 Great Diamond Island
Portland, Maine: Hidden Histories Guided Walking Tour
CA $76
per adult
Portland Smartphone Audio Tour: Self-Guided Drive
CA $24
per traveller
100% of travellers recommend
Portland, Maine: Black History Guided Walking Tour
CA $76
per adult
Frequently asked questions
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- Inn On Peaks Island
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- Long Creek Hotel by IHG
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- Portland Museum of Art
- Gooch's Beach
- Popham Beach State Park
- Westbrook Vacations
- Casco Vacations
- Camp Ellis Beach
- Higgins Beach
- Ll Bean Flagship Store
- Old Orchard Beach Pier
- East End Beach
- Freeport Vacations
- Portland Vacations
- Portland Head Light
- Visit Ferry Village
- Maine Mall
- South Portland Vacations
- Ogunquit Beach
- Desert of Maine
- Seashore Trolley Museum
- Windham Vacations
- Marden's Surplus and Salvage
- Palace Playland
- Visit Portland
- Bailey Island Vacations
- Kennebunkport Vacations
- Scarborough Vacations
- Scarborough Beach State Park
- Durham Vacations
- Aquaboggan Water Park
- Visit Old Orchard Beach
- Old Orchard Beach Vacations
- Visit Old Port
- Ocean Park Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
