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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.
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Save 100% on your flight
Price was $719, price is now $478 per person
$478
per person
Mar 6 - Mar 13
found 5 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 breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Portland Stage are located nearby.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Save 100% on your flight
Price was $880, price is now $545 per person
$545
per person
Mar 6 - Mar 13
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Sports Hall of Fame and Cathedral of the Immaculate Conception are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
Price was $766, price is now $509 per person
$509
per person
Mar 6 - Mar 13
found 5 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.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Save 100% on your flight
Price was $813, price is now $550 per person
$550
per person
Mar 6 - Mar 13
found 5 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.
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
Save 100% on your flight
Price was $745, price is now $533 per person
$533
per person
Mar 6 - Mar 13
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Tate House Museum and Thompson's Point are located nearby.
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Save 100% on your flight
Price was $685, price is now $495 per person
$495
per person
Mar 6 - Mar 13
found 5 hours ago
Roundtrip flight included
Chicago (ORD) 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 Casco Bay Lines Ferry Terminal and Maine Sports Hall of Fame are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,212, price is now $879 per person
$879
per person
Mar 6 - Mar 13
found 5 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.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $1,101, price is now $811 per person
$811
per person
Mar 6 - Mar 13
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this 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 Kennebunkport Village Green are located nearby.

Cumberland Foreside Vacation Packages 3-4 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
Price was $430, price is now $348 per person
$348
per person
Feb 1 - Feb 4
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $495, price is now $372 per person
$372
per person
Feb 1 - Feb 4
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $463, price is now $375 per person
$375
per person
Feb 1 - Feb 4
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $591, price is now $483 per person
$483
per person
Feb 1 - Feb 4
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)

Cumberland Foreside Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $719, price is now $478 per person
$478
per person
Mar 6 - Mar 13
found 5 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
Save 100% on your flight
Price was $880, price is now $545 per person
$545
per person
Mar 6 - Mar 13
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $766, price is now $509 per person
$509
per person
Mar 6 - Mar 13
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $813, price is now $550 per person
$550
per person
Mar 6 - Mar 13
found 5 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.

Breeze Airways
Mon, Jan 5 - Fri, Jan 9
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$158 Roundtrip, found 1 hour ago
$158
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Mon, Jan 5 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Fri, Jan 9, priced at $158 found 1 hour ago
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
Bargain Flight
Tue, Jan 20 - Sat, Jan 24
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$184 Roundtrip, found 4 days ago
$184
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Tue, Jan 20 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sat, Jan 24, priced at $184 found 4 days ago
American Airlines
Fri, Jan 30 - Mon, Feb 2
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$199 Roundtrip, found 8 hours ago
$199
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Jan 30 from Tampa Intl. to Portland Intl. Jetport, returning Mon, Feb 2, priced at $199 found 8 hours ago