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Great Diamond Island Vacation Packages

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A calm sea with a sailboat and rocky coastline.

Great Diamond Island
Portland
Maine
United States of America
North America
Hotwire.com

Great Diamond Island Flight + Hotel Packages

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

Nautical Mile

2.5 out of 5

Price was $712, price is now $569 per person

$569

per person

Dec 9 - Dec 12

found 4 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

Stay at this aparthotel in Wells. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Moody Beach and Footbridge Beach are located nearby.

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

84 Main

4 out of 5

Price was $1,026, price is now $873 per person

$873

per person

Dec 24 - Dec 27

found 11 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

Stay at this condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dock Square and Kennebunk Free Library are located nearby.

The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.

Reviewed on Jul 17, 2026

The Meadowmere Resort

2.5 out of 5

Price was $1,032, price is now $883 per person

$883

per person

Dec 24 - Dec 27

found 11 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Marginal Way and Ogunquit Beach are located nearby.

The Docent's Collection at 121 Middle Street

3.5 out of 5

Price was $681, price is now $596 per person

$596

per person

Jan 23 - Jan 25

found 6 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions State Theatre and Thompson's Point are located nearby.

We loved everything. The only thing is the mattress is a little soft and you easily roll to the middle!

Reviewed on Oct 27, 2026

Evalina Hotel

2.5 out of 5

Price was $817, price is now $718 per person

$718

per person

Jan 23 - Jan 25

found 6 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions State Theatre and Thompson's Point are located nearby.

Cape Arundel Inn and Resort

3 out of 5

Price was $1,343, price is now $1,179 per person

$1,179

per person

Dec 24 - Dec 27

found 11 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

Stay at this guesthouse in Kennebunkport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Dock Square and Colony Beach are located nearby.

A special hotel. Beautiful setting, unique one-of-kind inn. So very Maine coastal. Staff could not have been more appropriately available, helpful, kind. Lovely experience all around.

Reviewed on Oct 26, 2026

Blind Tiger Portland - Danforth Street.

3.5 out of 5

Price was $1,149, price is now $1,013 per person

$1,013

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions State Theatre and Cross Insurance Arena are located nearby.

Very helpful and friendly staff

Reviewed on Oct 28, 2026

Inn By The Sea

4 out of 5

Price was $1,045, price is now $928 per person

$928

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.