Name: Portland Regency Hotel & Spa
Price range: $179 total
Rating: 9.4

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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

Save 100% on your flight

$629

per person

Jun 19 - Jun 22

found 14 hours ago

Roundtrip non-stop flight included

Nashville (BNA) to Portland (PWM)

9/10 Wonderful! (1,000 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

Meadowmere Resort

Save 100% on your flight

$1,070

per person

Jul 23 - Jul 27

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

8.6/10 Excellent! (1,000 reviews)

Very well kept… great staff we had a great time

Reviewed on Apr 14, 2026

Saco Bay Hotel

Save 100% on your flight

$694

per person

Jun 16 - Jun 22

found 23 hours ago

Roundtrip non-stop flight included

Nashville (BNA) to Portland (PWM)

7.6/10 Good! (1,050 reviews)

Very clean, friendly staff, great breakfast. Would stay again

Reviewed on May 3, 2026

Portland Harbor Hotel

Downtown Portland

Save 100% on your flight

$1,785

per person

Jun 16 - Jun 22

found 23 hours ago

Roundtrip non-stop flight included

Nashville (BNA) to Portland (PWM)

9.2/10 Wonderful! (1,751 reviews)

We (and our kids!) loved the “pantry” on each floor — fruit, snacks, cookies, tea, coffee. It was a much-appreciated surprise. Room was clean and quiet, and all staff were friendly and helpful.

Reviewed on Apr 29, 2026

Cliff House Maine

Bald Head

Save 100% on your flight

$2,223

per person

Jul 5 - Jul 10

found 13 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

9.4/10 Exceptional! (1,002 reviews)

all was great. my favorite place!

Reviewed on Apr 29, 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

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

$221 nightly

$244 total

May 10 - May 11

Total with taxes and fees

9.4/10 Exceptional! (1,754 reviews)

Hotel was within walking distance to everything we wanted! Friendly, helpful staff, bartender was great! Extremely clean hotel, would absoulty stay again!

Reviewed on May 4, 2026

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Fully refundable

$169 nightly

$187 total

May 26 - May 27

Total with taxes and fees

9.4/10 Exceptional! (1,205 reviews)

This was a very relaxing stay with a helpful

Reviewed on May 5, 2026

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Fully refundableReserve now, pay when you stay

$162 nightly

$179 total

May 26 - May 27

Total with taxes and fees

9.4/10 Exceptional! (1,640 reviews)

A fantastic hotel, super clean, comfortable/cozy rooms and friendly staff. The shuttle to/from the airport was an added bonus and appreciated all the great recommendations from the driver. Would absolutely stay here again!

Reviewed on May 5, 2026

See all 2,364 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.