Search Deals onChebeague Island Vacation Packages
Chebeague Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The McKernan Inn
Save 100% on your flight
per person
Aug 10 - Aug 13
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Stay at this 3-star beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions State Theatre and Thompson's Point are located nearby.
Cliff House Maine
Save 100% on your flight
per person
Sep 23 - Sep 30
found 16 hours ago
Roundtrip non-stop flight included
Tulsa (TUL) 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.
Chebeague Island Inn
Save 100% on your flight
per person
Sep 23 - Sep 30
found 16 hours ago
Roundtrip non-stop flight included
Tulsa (TUL) 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.
Portland Harbor Hotel
Save 100% on your flight
per person
Aug 10 - Aug 17
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.
Inn By The Sea
Save 100% on your flight
per person
Aug 23 - Aug 27
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this 4-star luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
The Weldon Hotel
Save 100% on your flight
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Portland (PWM)
Stay at this 4.5-star luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions State Theatre and Thompson's Point are located nearby.
Kennebunkport Captains Collection
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Blind Tiger Portland – Carleton Street
Save 100% on your flight
per person
Aug 18 - Aug 21
found 4 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions State Theatre and Thompson's Point are located nearby.
Chebeague Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chebeague 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 1 day ago
$117
Roundtrip
found 1 day ago
Tue, Aug 5 - Wed, Aug 13
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Tue, Jul 29 - Thu, Jul 31
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$155 Roundtrip, found 7 hours ago
$155
Roundtrip
found 7 hours ago
Tue, Sep 30 - Wed, Oct 1
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$157 Roundtrip, found 4 hours ago
$157
Roundtrip
found 4 hours ago
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