Search Deals onChebeague Island Vacation Packages
Chebeague Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
And. N B&B
per person
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Portland (PWM)
Stay at this 3-star B&B in Gray. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Spring Meadows Golf Course and Little Sebago Lake are located nearby.
Waldo Emerson Inn
Save 100% on your flight
per person
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Portland (PWM)
Stay at this 3-star B&B in Kennebunk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the property condition in our reviews. Popular attractions Wedding Cake House and Kennebunk Dog Park are located nearby.
Portland Harbor Hotel
Save 100% on your flight
per person
Jun 27 - Jul 1
found 10 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Inn By The Sea
Save 100% on your flight
per person
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Portland (PWM)
Stay at this 4-star aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Thompson's Point and Maine Mall are located nearby.
The Docent's Collection
Save 100% on your flight
per person
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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.
Hampton Inn Portland Downtown - Waterfront
per person
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Blind Tiger Portland - Danforth Street.
Save 100% on your flight
per person
May 28 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Thompson's Point and Maine Mall 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.
Mon, Apr 21 - Sun, May 4
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$91 Roundtrip, found 4 days ago
$91
Roundtrip
found 4 days ago
Mon, Jul 28 - Thu, Jul 31
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$117 Roundtrip, found 13 hours ago
$117
Roundtrip
found 13 hours ago
Sat, Jul 5 - Sat, Jul 5
LGA
LaGuardia
PWM
Portland Intl. Jetport
$159 Roundtrip, found 4 days ago
$159
Roundtrip
found 4 days ago
Thu, Apr 24 - Sun, Apr 27
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
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