Search Deals onCumberland Vacation Packages
Cumberland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
River View Resort
Save 100% on your flight
per person
Jun 18 - Jun 23
found 23 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Portland (PWM)
Stay at this motel in Bethel. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Sunday River and Bethel Pathway are located nearby.
Nautical Mile
Save 100% on your flight
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) to Portland (PWM)
Stay at this aparthotel in Wells. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Moody Beach and Ogunquit Beach are located nearby.
AWOL Kennebunkport
Save 100% on your flight
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this 3-star 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 Kennebunkport Village Green and W. Robert Paine Gallery are located nearby.
Portland Harbor Hotel
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Charleston (CHS) 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.
Ogunquit River Inn & Suites
Save 100% on your flight
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Book a stay at this 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 Moody Beach and Ogunquit Beach are located nearby.
Nonantum Resort
Save 100% on your flight
per person
Jul 13 - Jul 18
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Stay at this 3.5-star hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions St. Anthony's Franciscan Monastery and Kennebunkport Village Green are located nearby.
Cambria Hotel Portland Downtown-Old Port
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Charleston (CHS) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Kennebunkport Captains Collection
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Charleston (CHS) 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 Kennebunkport Village Green and W. Robert Paine Gallery are located nearby.
Cumberland Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Cumberland 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, Jun 21 - Sat, Jun 28
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$120 Roundtrip, found 2 days ago
$120
Roundtrip
found 2 days ago
Tue, Jul 1 - Thu, Jul 3
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$153 Roundtrip, found 5 days ago
$153
Roundtrip
found 5 days ago
Mon, Jul 14 - Wed, Jul 16
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$155 Roundtrip, found 8 hours ago
$155
Roundtrip
found 8 hours ago
Mon, Aug 11 - Thu, Aug 14
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
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