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Cumberland Foreside Vacation Packages

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Cumberland Foreside Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Lake Wentworth Inn

Lake Wentworth Inn

2 out of 5
Price was $507, price is now $413 per person
$413
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,211, price is now $805 per person
$805
per person
Oct 24 - Oct 27
found 19 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.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $1,129, price is now $841 per person
$841
per person
Nov 24 - Nov 30
just found
Roundtrip flight included
New York (NYC) 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.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,545, price is now $1,199 per person
$1,199
per person
Nov 26 - Nov 30
found 10 hours ago
Roundtrip flight included
New York (LGA) 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.
Nonantum Resort

Nonantum Resort

3.5 out of 5
Price was $709, price is now $560 per person
$560
per person
Oct 24 - Oct 27
found 19 hours ago
Roundtrip flight included
New York (NYC) 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 Dock Square and Wells Beach are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $882, price is now $697 per person
$697
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
The Docent's Collection

The Docent's Collection

3.5 out of 5
Price was $1,230, price is now $993 per person
$993
per person
Nov 26 - Nov 30
found 10 hours ago
Roundtrip flight included
New York (LGA) 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.
River View Resort

River View Resort

2.5 out of 5
Price was $773, price is now $639 per person
$639
per person
Oct 11 - Oct 14
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.

Cumberland Foreside Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Nonantum Resort

Nonantum Resort

3.5 out of 5
Price was $709, price is now $560 per person
$560
per person
Oct 24 - Oct 27
found 19 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,211, price is now $805 per person
$805
per person
Oct 24 - Oct 27
found 19 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $1,090, price is now $833 per person
$833
per person
Oct 24 - Oct 27
found 19 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,545, price is now $1,199 per person
$1,199
per person
Nov 26 - Nov 30
found 10 hours ago
Roundtrip flight included
New York (LGA) to Portland (PWM)

Cumberland Foreside Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $809, price is now $550 per person
$550
per person
Nov 24 - Nov 30
found 5 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,627, price is now $1,165 per person
$1,165
per person
Nov 24 - Nov 30
just found
Roundtrip flight included
New York (NYC) to Portland (PWM)
The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,183, price is now $855 per person
$855
per person
Nov 24 - Nov 30
found 5 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $1,129, price is now $841 per person
$841
per person
Nov 24 - Nov 30
just found
Roundtrip flight included
New York (NYC) to Portland (PWM)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Delta
Fri, Oct 17 - Wed, Oct 22
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$107 Roundtrip, found 7 hours ago
$107
Roundtrip
found 7 hours ago
Select Delta flight, departing Fri, Oct 17 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Wed, Oct 22, priced at $107 found 7 hours ago
United
Fri, Oct 24 - Sun, Oct 26
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$109 Roundtrip, found 15 hours ago
$109
Roundtrip
found 15 hours ago
Select United flight, departing Fri, Oct 24 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Sun, Oct 26, priced at $109 found 15 hours ago
Delta
Wed, Oct 15 - Thu, Oct 23
LGA
LaGuardia
PWM
Portland Intl. Jetport
$119 Roundtrip, found 15 hours ago
$119
Roundtrip
found 15 hours ago
Select Delta flight, departing Wed, Oct 15 from LaGuardia to Portland Intl. Jetport, returning Thu, Oct 23, priced at $119 found 15 hours ago
Delta
Tue, Sep 30 - Thu, Oct 9
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$180 Roundtrip, found 4 hours ago
$180
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Sep 30 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Thu, Oct 9, priced at $180 found 4 hours ago