Search Deals on
Great Diamond Island Vacation Packages

Build your package with 2 more options

Leaving from

Going to

Departing

Returning

Travelers

Room 1

Adults

ChildrenAges 2 to 17

InfantsYounger than 2

Add specific hotel dates

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.

The Meadowmere Resort

2.5 out of 5

Save 100% on your flight

Price was $1,092, price is now $743 per person

$743

per person

Jun 28 - Jul 2

found 23 hours ago

Roundtrip flight included

Chicago (ORD) 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.

Portland Harbor Hotel

4 out of 5

Save 100% on your flight

Price was $1,742, price is now $1,259 per person

$1,259

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Cross Insurance Arena are located nearby.

Newagen Seaside Inn

3.5 out of 5

Price was $1,722, price is now $1,244 per person

$1,244

per person

Aug 9 - Aug 14

found 24 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Portland (PWM)

Book a stay at this family-friendly hotel in Southport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Southport Memorial Library and Hendricks Hill Museum are located nearby.

Cliff House Maine

4.5 out of 5

Save 100% on your flight

Price was $2,050, price is now $1,487 per person

$1,487

per person

Jun 28 - Jul 2

found 23 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

Book a stay at this luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Ogunquit Beach and Perkins Cove are located nearby.

Admiral Peary Inn

3 out of 5

Price was $1,045, price is now $793 per person

$793

per person

Jul 23 - Jul 26

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

Stay at this B&B in Fryeburg. Enjoy free WiFi, free parking, and a garden. Popular attractions Fryeburg Public Library and Bradley Memorial Park are located nearby.

Hilton Garden Inn Freeport Downtown

3 out of 5

Price was $1,320, price is now $1,029 per person

$1,029

per person

Aug 9 - Aug 14

found 24 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Portland (PWM)

Book a stay at this business-friendly hotel in Freeport. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions LL Bean Flagship Store and Freeport Historical Society are located nearby.

1802 House Bed and Breakfast

3.5 out of 5

Price was $1,520, price is now $1,207 per person

$1,207

per person

Jul 23 - Jul 26

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

Book a stay at this golf B&B in Kennebunkport. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Dock Square and Wells Beach are located nearby.

Portland Regency Hotel & Spa

3.5 out of 5

Price was $2,001, price is now $1,599 per person

$1,599

per person

Jul 17 - Jul 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Portland Head Light are located nearby.