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.
Microtel Inn & Suites by Wyndham York
Save 100% on your flight
per person
Sep 2 - Sep 7
found 9 hours ago
Roundtrip flight included
Nashville (BNA) 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.
Chebeague Island Inn
Save 100% on your flight
per person
Sep 22 - Sep 26
found 21 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Portland (PWM)
Stay at this 4-star beach hotel in Chebeague Island. Enjoy free WiFi, breakfast (surcharge), and a free ferry terminal shuttle. Popular attractions Little John Island Preserve and Winslow Memorial Park are located nearby.
River View Resort
Save 100% on your flight
per person
Sep 2 - Sep 7
found 9 hours ago
Roundtrip flight included
Nashville (BNA) 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.
Ramada Plaza by Wyndham Portland
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Portland Harbor Hotel
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.
Cliff House Maine
Save 100% on your flight
per person
Aug 11 - Aug 14
found 3 hours ago
Roundtrip flight included
New York (NYC) 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.
Days Inn by Wyndham Airport/Maine Mall
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Portland (PWM)
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby.
Kennebunkport Captains Collection
Save 100% on your flight
per person
Sep 2 - Sep 7
found 9 hours ago
Roundtrip flight included
Nashville (BNA) 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.
Tue, Sep 16 - Tue, Sep 30
LGA
LaGuardia
PWM
Portland Intl. Jetport
$117 Roundtrip, found 17 hours ago
$117
Roundtrip
found 17 hours ago
Wed, Aug 6 - Tue, Aug 12
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$119 Roundtrip, found 1 hour ago
$119
Roundtrip
found 1 hour ago
Tue, Jul 29 - Thu, Jul 31
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Tue, Sep 9 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$159 Roundtrip, found 8 hours ago
$159
Roundtrip
found 8 hours ago
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Car Rentals in Great Diamond Island
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