Great Diamond Island Vacation Packages 2026 from $680

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The Latest Great Diamond Island vacation packages

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

Nautical Mile

$680

per person

Dec 4 - Dec 8

found 17 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

8.6/10 Excellent! (24 reviews)

I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.

Reviewed on Sep 8, 2026

Evalina Hotel

Downtown Portland

Save 100% on your flight

$1,133

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

10/10 Exceptional! (11 reviews)

This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class.

Reviewed on Sep 24, 2026

Blind Tiger Portland – Carleton Street

West End

$683

per person

Dec 3 - Dec 6

found 8 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

9.6/10 Exceptional! (129 reviews)

Beautiful place

Reviewed on Sep 20, 2026

The Docent's Collection at 121 Middle Street

Downtown Portland

$733

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

9.6/10 Exceptional! (382 reviews)

The loft was wonderful! Really great location for old port! Really enjoyed our stay! Felt homely! We relaxed and felt so comfortable there! Would recommend!

Reviewed on Sep 24, 2026

Blind Tiger Portland - Danforth Street.

West End

$770

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

9.6/10 Exceptional! (192 reviews)

Place was charming and quirky. Very comfortable and well located.

Reviewed on Sep 18, 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: Casco Bay Morning Lighthouse Cruise

$59

per adult

80% of travellers recommend

See all activities in Great Diamond Island

Great Diamond Island Hotel Deals

Quality Inn & Suites South Portland

738 Main Street South Portland ME

Fully refundable

$82 nightly

$90 total

Oct 25 - Oct 26

Total with taxes and fees

6.4/10 (1,136 reviews)

"Perfect for a short get away."

Reviewed on Sep 25, 2026

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

80 John Roberts Rd. South Portland ME

Fully refundable

$93 nightly

$101 total

Oct 25 - Oct 26

Total with taxes and fees

8.4/10 Very Good! (2,991 reviews)

"Simple operation. Good ice machine."

Reviewed on Sep 24, 2026

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Fully refundableReserve now, pay when you stay

$93 nightly

$103 total

Oct 25 - Oct 26

Total with taxes and fees

8.2/10 Very Good! (1,724 reviews)

"Very clean. Mattress needs to be replaced, but overall, the stay was fine."

Reviewed on Sep 25, 2026

See all 2,439 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.