Search Deals onGreat Diamond Island Vacation Packages
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Great Diamond Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Tamworth
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Book a stay at this business-friendly motel in Chocorua. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White Lake State Park and White Lake are located nearby.
Ogunquit River Inn & Suites
Save 100% on your flight
per person
Oct 3 - Oct 6
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Moody Beach are located nearby.
River View Resort
Save 100% on your flight
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Stay at this motel in Bethel. Enjoy free WiFi, free parking, and 4 outdoor pickleball courts. Our guests praise the helpful staff in our reviews. Popular attractions Sunday River and Bethel Pathway are located nearby.
Purity Spring Resort
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Book a stay at this ski hotel in Madison. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions King Pine Ski Area and Ossipee Lake Marina are located nearby.
InnSeason Resorts The Falls at Ogunquit
Save 100% on your flight
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Ogunquit Beach and Moody Beach are located nearby.
Microtel Inn & Suites by Wyndham York
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Book a stay at this business-friendly hotel in York. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Long Sands Beach and Short Sands Beach are located nearby.
Cliff House Maine
Save 100% on your flight
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Stay at this 4.5-star 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.
Kennebunkport Captains Collection
per person
Aug 30 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 4.5-star luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Goose Rocks Beach are located nearby.
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, Aug 16 - Sat, Aug 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Wed, Oct 15 - Sat, Oct 18
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Tue, Sep 16 - Tue, Sep 30
LGA
LaGuardia
PWM
Portland Intl. Jetport
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Tue, Sep 2 - Tue, Sep 9
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
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