
Great Diamond Island Fishing Vacations
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Flight and Fishing hotel deals in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.


Portland Harbor Hotel
Downtown Portland
Price was CA $3,072, price is now CA $2,384 per person
CA $2,384
per person
Aug 7 - Aug 11
found 10 hours ago
Roundtrip flight included
Edmonton (YEG) to Portland (PWM)
9.4/10 Exceptional! (1,774 reviews)
An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow.
Reviewed on May 25, 2026

The Weldon Hotel
Downtown Portland
Price was CA $2,955, price is now CA $2,439 per person
CA $2,439
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless,
Great location. Would stay here again
Reviewed on Apr 23, 2026

Longfellow Hotel
Parkside
Price was CA $2,846, price is now CA $2,492 per person
CA $2,492
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
Clean, comfortable rooms. Hotel does have a few food options near by but car service was wonderful as it’s not near most of the restaurants & shops. Overall great hotel!
Reviewed on May 17, 2026

Holiday Inn Portland-By the Bay by IHG
Downtown Portland
Price was CA $1,776, price is now CA $1,626 per person
CA $1,626
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (1,553 reviews)
The room was clean, but nothing special for the price per night. I really expect a bit more for $400+/night.
That said, the staff were friendly, the breakfast buffet with omelet bar was nice and good quality food (not included in price of hotel), walkable to the Old Port.
Reviewed on May 24, 2026
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View all trips5* Fishing holidays in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.

White Barn Inn & Spa, Auberge Collection
Price was CA $5,850, price is now CA $5,363 per person
CA $5,363
per person
Jul 22 - Jul 25
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (117 reviews)
The White Barn Inn was first class from check in to check out! It has the wow factor we love - complimentary valet parking, welcome cocktails, basket of treats waiting in our room, coffee & pastry delivered to our door at our preferred time each morning, turn down service, incredible staff, delicious restaurant, and perfect location. We will definitely return!
Reviewed on May 12, 2026
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View all trips3 Night Fishing holidays in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.


Portland Harbor Hotel
Downtown Portland
Price was CA $2,173, price is now CA $1,824 per person
CA $1,824
per person
Jul 9 - Jul 12
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (1,774 reviews)
An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow.
Reviewed on May 25, 2026

White Barn Inn & Spa, Auberge Collection
Price was CA $5,850, price is now CA $5,363 per person
CA $5,363
per person
Jul 22 - Jul 25
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (117 reviews)
The White Barn Inn was first class from check in to check out! It has the wow factor we love - complimentary valet parking, welcome cocktails, basket of treats waiting in our room, coffee & pastry delivered to our door at our preferred time each morning, turn down service, incredible staff, delicious restaurant, and perfect location. We will definitely return!
Reviewed on May 12, 2026
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View all trips4 Night Fishing holidays in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.

1802 House Bed and Breakfast
Price was CA $2,464, price is now CA $2,106 per person
CA $2,106
per person
Aug 7 - Aug 11
found 10 hours ago
Roundtrip flight included
Edmonton (YEG) to Portland (PWM)
9.8/10 Exceptional! (106 reviews)
Juliana was wonderful made you feel like you were part of her family breakfast each morning was homemade and delicious!
Such a cozy, clean comfortable in Inn
Reviewed on May 14, 2026

Portland Harbor Hotel
Downtown Portland
Price was CA $3,072, price is now CA $2,384 per person
CA $2,384
per person
Aug 7 - Aug 11
found 10 hours ago
Roundtrip flight included
Edmonton (YEG) to Portland (PWM)
9.4/10 Exceptional! (1,774 reviews)
An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow.
Reviewed on May 25, 2026

The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $3,703, price is now CA $3,063 per person
CA $3,063
per person
Aug 7 - Aug 11
found 10 hours ago
Roundtrip flight included
Edmonton (YEG) to Portland (PWM)
9.6/10 Exceptional! (307 reviews)
Located midway between the Arts District along Congress Street and the Port District along Commercial Street, this property is very convenient, but admittedly a little hard to find. These are loft units in a building that is otherwise unmarked, situated more like an apartment building with storefronts at street level. But once you find where it is and where to enter, the rest is pretty simple. The loft we stayed in was very much like a large one-bedroom apartment, with a full kitchen, full bath and all necessary amenities. There is a self-parking garage adjacent to the building to park your vehicle (an additional charge), which allows you the convenience of walking to the local sights, shops and restaurants in the area, of which there are many. Overall, a very comfortable stay.
Reviewed on May 26, 2026
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