Name: Portland Regency Hotel & Spa
Price range: $218 total
Rating: 9.4

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Great Diamond Island vacation packages

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

Saco Bay Hotel

Save 100% on your flight

$924

per person

Jul 19 - Jul 25

found 21 hours ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

7.6/10 Good! (1,049 reviews)

We just had a night stay there during a journey but it was comfortable and what we needed

Reviewed on May 7, 2026

The Meadowmere Resort

Save 100% on your flight

$1,350

per person

Jul 19 - Jul 25

found 21 hours ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

8.6/10 Excellent! (1,001 reviews)

Very well kept… great staff we had a great time

Reviewed on Apr 14, 2026

Ogunquit River Inn & Suites

Save 100% on your flight

$1,122

per person

Jul 19 - Jul 25

found 21 hours ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9/10 Wonderful! (1,003 reviews)

The front desk was incredibly nice. They moved us closer to our family in another room without being asked. It was very appreciated, thank you.

Reviewed on May 3, 2026

Portland Harbor Hotel

Downtown Portland

Save 100% on your flight

$1,636

per person

Jul 19 - Jul 25

found 21 hours ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.2/10 Wonderful! (1,751 reviews)

Everything was clean.

Reviewed on May 9, 2026

The Docent's Collection at 121 Middle Street

Downtown Portland

Save 100% on your flight

$2,233

per person

Jul 19 - Jul 25

found 21 hours ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.6/10 Exceptional! (300 reviews)

This accommodation was in an excellent location for restaurants and attending events. We were able to park our car and walk without concern. We found the accommodation well furnished with a well equipped kitchen. We would have liked to stay longer and will likely return.

Reviewed on May 5, 2026

Don't see what you're looking for?

See all available trips from Columbus to Great Diamond Island

View all trips

Discover the most popular places to visit in Great Diamond Island

State Theatre

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

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.

Great Diamond Island Hotel Deals

Portland Harbor Hotel

468 Fore Street Portland ME

Fully refundableReserve now, pay when you stay

$241 nightly

$266 total

May 25 - May 26

Total with taxes and fees

9.4/10 Exceptional! (1,760 reviews)

Everything was clean.

Reviewed on May 9, 2026

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

340 Park Ave Portland ME

Fully refundableReserve now, pay when you stay

$96 nightly

$107 total

May 11 - May 12

Total with taxes and fees

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Fully refundableReserve now, pay when you stay

$197 nightly

$218 total

May 17 - May 18

Total with taxes and fees

9.4/10 Exceptional! (1,643 reviews)

Very nice for pets!

Reviewed on May 7, 2026

See all 2,369 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.