Name: HomeAwhile
Price range: $127 total
Rating: 9.6

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The Latest Great Diamond Island vacation packages

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

Ogunquit River Inn & Suites

$954

per person

Jul 5 - Jul 10

found 23 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

9/10 Wonderful! (1,000 reviews)

The room was very clean!

Reviewed on Oct 31, 2025

Cliff House Maine

Bald Head

Save 100% on your flight

$2,208

per person

Jun 28 - Jul 3

found 7 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

9.4/10 Exceptional! (1,006 reviews)

Need to book everything in advance before arriving at the resort. Staff was excellent! Everything is very expensive. Valet is not included.

Reviewed on Apr 20, 2026

Newagen Seaside Inn

$1,022

per person

Jun 28 - Jul 3

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

9.4/10 Exceptional! (341 reviews)

IT WAS CHARMING AND BEAUTIFUL. The restaurant was wonderful, all the staff was first class, would love to go back.

Reviewed on Oct 14, 2025

The Weldon Hotel

Downtown Portland

$1,086

per person

Jun 3 - Jun 6

found 1 day ago

Roundtrip flight included

Denver (DEN) to Portland (PWM)

9.8/10 Exceptional! (100 reviews)

Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again

Reviewed on Apr 23, 2026

Blind Tiger Portland - Danforth Street.

West End

Save 100% on your flight

$1,572

per person

Jun 3 - Jun 6

found 1 day ago

Roundtrip flight included

Denver (DEN) to Portland (PWM)

9.6/10 Exceptional! (180 reviews)

The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!

Reviewed on Mar 10, 2026

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Discover the most popular places to visit in Great Diamond Island

State Theatre

4.5/5(88 reviews)

The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.

Portland Museum of Art

4.5/5(258 reviews)

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

What to do in Great Diamond Island

Portland Smartphone Audio Tour: Self-Guided Drive

$15

per traveler

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

$10

per traveler

Ultimate Portland Self-Guided Driving GPS Audio Tour

$17

per traveler

100% of travellers recommend

See all activities in Great Diamond Island

Great Diamond Island Hotel Deals

Portland Harbor Hotel

468 Fore Street Portland ME

Fully refundableReserve now, pay when you stay

$212 nightly

$235 total

May 3 - May 4

Total with taxes and fees

9.2/10 Wonderful! (1,754 reviews)

Highly recommended! Very clean and staff were amazing!!

Reviewed on Apr 28, 2026

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Fully refundable

$154 nightly

$170 total

Apr 29 - Apr 30

Total with taxes and fees

9.4/10 Exceptional! (1,199 reviews)

Reception was very helpful.

Reviewed on Apr 28, 2026

HomeAwhile

205 Southborough Drive Scarborough ME

Fully refundableReserve now, pay when you stay

$116 nightly

$127 total

May 21 - May 22

Total with taxes and fees

9.6/10 Exceptional! (27 reviews)

Air conditioning system was making loud clap every 10 minutes, not restful sleep. We arrived late at night, so unfortunately, did not notice right away. We reserved two rooms via Expedia. Upon arrival we were told we have only one room reserved. At the end, hotel was able to find another room for ...

Reviewed on Apr 26, 2026

See all 2,357 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.