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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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $566, price is now $436 per person
$436
per person
Feb 13 - Feb 15
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Fore Street Gallery are located nearby.
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
Price was $789, price is now $505 per person
$505
per person
Feb 18 - Feb 21
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in South Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maine Mall and Nonesuch River Golf Club are located nearby.
Portland Sheraton at Sable Oaks

Portland Sheraton at Sable Oaks

4 out of 5
Price was $818, price is now $574 per person
$574
per person
Feb 18 - Feb 21
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in South Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Maine Mall and Nonesuch River Golf Club are located nearby.
The Kennebunk Inn

The Kennebunk Inn

2.5 out of 5
Save 100% on your flight
Price was $587, price is now $447 per person
$447
per person
Mar 26 - Apr 1
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Kennebunk. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Dock Square and Kennebunk Free Library are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $847, price is now $681 per person
$681
per person
Feb 13 - Feb 15
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Victoria Mansion and Portland Club are located nearby.
Meadowmere Resort

Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $747, price is now $610 per person
$610
per person
Mar 26 - Apr 1
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this spa hotel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Marginal Way and Ogunquit Beach are located nearby.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $565, price is now $462 per person
$462
per person
Feb 13 - Feb 15
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions N.W. Barrett Gallery and Fore Street Gallery are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $639, price is now $527 per person
$527
per person
Feb 13 - Feb 15
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this 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.

Cumberland Foreside Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
Price was $789, price is now $505 per person
$505
per person
Feb 18 - Feb 21
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Portland Sheraton at Sable Oaks

Portland Sheraton at Sable Oaks

4 out of 5
Price was $818, price is now $574 per person
$574
per person
Feb 18 - Feb 21
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $803, price is now $610 per person
$610
per person
Mar 26 - Mar 29
found 12 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $686, price is now $555 per person
$555
per person
Mar 26 - Mar 29
found 12 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Portland (PWM)

Cumberland Foreside Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Kennebunk Inn

The Kennebunk Inn

2.5 out of 5
Save 100% on your flight
Price was $587, price is now $447 per person
$447
per person
Mar 26 - Apr 1
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,098, price is now $795 per person
$795
per person
Mar 26 - Apr 1
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $1,148, price is now $848 per person
$848
per person
Mar 13 - Mar 19
found 6 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $1,022, price is now $778 per person
$778
per person
Mar 26 - Apr 1
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)

Top Flight Deals

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

American Airlines
Wed, May 27 - Tue, Jun 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$183 Roundtrip, just found
$183
Roundtrip
just found
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Jun 2, priced at $183 just found
Delta
Tue, Feb 3 - Sat, Feb 7
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$183 Roundtrip, found 23 hours ago
$183
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Feb 3 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Feb 7, priced at $183 found 23 hours ago
American Airlines
Tue, Feb 17 - Tue, Feb 24
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$189 Roundtrip, found 16 hours ago
$189
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Tue, Feb 17 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Tue, Feb 24, priced at $189 found 16 hours ago
American Airlines
Fri, Jan 23 - Sat, Jan 24
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$194 Roundtrip, found 4 days ago
$194
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Jan 23 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sat, Jan 24, priced at $194 found 4 days ago