Search Deals onChebeague Island Vacation Packages
Chebeague Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Lake Wentworth Inn
Save 100% on your flight
Price was $455, price is now $357 per person
$357
per person
Oct 1 - Oct 4
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
Stay at this hotel in Wolfeboro. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New Hampshire Boat Museum and Allen Albee Beach are located nearby.
The McKernan Inn
Save 100% on your flight
Price was $578, price is now $369 per person
$369
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Portland (PWM)
Stay at this 3-star beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thompson's Point and Maine Mall are located nearby.
Cliff House Maine
Save 100% on your flight
Price was $1,197, price is now $841 per person
$841
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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
Save 100% on your flight
Price was $747, price is now $531 per person
$531
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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 Wells Beach are located nearby.
The Docent's Collection
Save 100% on your flight
Price was $960, price is now $699 per person
$699
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Portland (PWM)
Stay at this 3.5-star hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Thompson's Point and Maine Mall are located nearby.
Inn By The Sea
Save 100% on your flight
Price was $884, price is now $655 per person
$655
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
Portland Harbor Hotel
Price was $566, price is now $430 per person
$430
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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 Thompson's Point and Maine Mall are located nearby.
Chebeague Island Inn
Save 100% on your flight
Price was $810, price is now $646 per person
$646
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
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.
Fri, Oct 17 - Wed, Oct 22
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$107 Roundtrip, found 3 hours ago
$107
Roundtrip
found 3 hours ago
Sun, Sep 14 - Tue, Sep 30
LGA
LaGuardia
PWM
Portland Intl. Jetport
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Mon, Sep 15 - Tue, Sep 23
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$161 Roundtrip, found 1 day ago
$161
Roundtrip
found 1 day ago
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$172 Roundtrip, found 13 hours ago
$172
Roundtrip
found 13 hours ago
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