Great Diamond Island Vacation Packages 2026 from $495

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The Latest Great Diamond Island vacation packages

Price found within the past 48 hours. Click for updated prices.

The Wolfeboro Inn

Save 100% on your flight

$495

per person

Oct 13 - Oct 16

found 18 hours ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

8.2/10 Very Good! (628 reviews)

Great location

Reviewed on Aug 24, 2026

Admiral Peary Inn

Save 100% on your flight

$809

per person

Oct 10 - Oct 13

found 19 hours ago

Roundtrip non-stop flight included

Denver (DEN) to Portland (PWM)

8.8/10 Excellent! (57 reviews)

Super nostalgic, unique, great to walk through the place and learn so much history. Like staying in a mini museum.

Reviewed on Aug 19, 2026

Nautical Mile

Save 100% on your flight

$684

per person

Nov 14 - Nov 20

found 1 day ago

Roundtrip flight included

New York (NYC) to Portland (PWM)

8.6/10 Excellent! (24 reviews)

Bel endroit où séjourner! Tout près de Well’s Beach.

Reviewed on Jul 27, 2026

The Meadowmere Resort

Save 100% on your flight

$829

per person

Oct 1 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Portland (PWM)

8.6/10 Excellent! (1,002 reviews)

Room was clean and staff was helpful but this is supposed to a good quality hotel yet it’s on the main road with lots of associated noice including morning garbage pickup, etc. Also this property has absolutely no view.

Reviewed on Aug 26, 2026

Blind Tiger Portland - Danforth Street.

West End

Save 100% on your flight

$1,745

per person

Oct 22 - Oct 25

found 23 hours ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.6/10 Exceptional! (189 reviews)

Perfect location & beautiful stay! Very unique property. Great recommendations & lovely hospitality. We will definitely come back the next time we’re in Portland! :)

Reviewed on Aug 23, 2026

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What to do in Great Diamond Island

Sunset Windjammer Cruise Along the Coast of Portland Maine

$77

per adult

90% of travellers recommend

Portland Lighthouse Boat Cruise with Oysters & Prosecco

Portland Explorer: Boat Cruise with Oysters & Prosecco

$137

per adult

See all activities in Great Diamond Island

Great Diamond Island Hotel Deals

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

Fully refundable

$72 nightly

$78 total

Sep 2 - Sep 3

Total with taxes and fees

7.2/10 Good! (732 reviews)

"Was once a nice place but it’s being run hard and not reinvested in. Bed was comfortable but over all, it’s mid and not looking like it’s being taken care of."

Reviewed on Aug 26, 2026

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

$110 nightly

$121 total

Sep 2 - Sep 3

Total with taxes and fees

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Fully refundable

$78 nightly

$85 total

Sep 2 - Sep 3

Total with taxes and fees

6.4/10 (1,089 reviews)

"Cheap"

Reviewed on Aug 26, 2026

See all 2,459 properties in Great Diamond Island

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.