Search Deals onGreat Diamond Island Vacation Packages
Great Diamond Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Inn at St John Portland In-Town
Price was $941, price is now $752 per person
$752
per person
Dec 21 - Dec 28
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 free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
No elevator. Steep stairs!
Reviewed on Oct 2, 2026
Evalina Hotel
Save 100% on your flight
Price was $2,546, price is now $1,803 per person
$1,803
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Better than expected. This new property was in a great location. Easy to walk to restaurants and shopping. Comfortable bed, nice bathroom and a sitting area with sofa, chair and tv. I was a little concerned because we could hear music from a nearby bar, but everything stopped by 10 o’clock. Would return.
Reviewed on Sep 25, 2026
The Docent's Collection at 178 Middle Street
Save 100% on your flight
Price was $2,077, price is now $1,551 per person
$1,551
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
The Docent's Collection at 121 Middle Street
Price was $1,916, price is now $1,438 per person
$1,438
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Blind Tiger Portland - Danforth Street.
Price was $2,032, price is now $1,547 per person
$1,547
per person
Dec 21 - Dec 28
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 Cross Insurance Arena and Maine Mall are located nearby.
Inn By The Sea
Price was $1,768, price is now $1,391 per person
$1,391
per person
Dec 21 - Dec 28
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.
Portland Harbor Hotel
Price was $1,112, price is now $881 per person
$881
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip non-stop 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 Cross Insurance Arena and Maine Mall are located nearby.
Grand Beach Inn
Price was $1,213, price is now $996 per person
$996
per person
Dec 21 - Dec 28
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Old Orchard Beach. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Old Orchard Beach and Grand Beach are located nearby.
Great little spot, perfect beach walk
Reviewed on Oct 2, 2026
Great Diamond Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Great Diamond Island Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$182 Roundtrip, just found
$182
Roundtrip
just found
Thu, Dec 3 - Tue, Dec 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$207 Roundtrip, found 2 hours ago
$207
Roundtrip
found 2 hours ago
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$219 Roundtrip, found 4 hours ago
$219
Roundtrip
found 4 hours ago
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