Cumberland Center Vacations

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Cumberland Center Flight + Hotel packages

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 $912, price is now $656 per person
$656
per person
Apr 18 - Apr 24
found 1 day 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 Maine Mall and Cross Insurance Arena are located nearby.

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,039, price is now $715 per person
$715
per person
Apr 18 - Apr 24
found 1 day 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 Mall and Cathedral of the Immaculate Conception are located nearby.

84 Main

84 Main

4 out of 5
Save 100% on your flight
Price was $987, price is now $690 per person
$690
per person
Apr 18 - Apr 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Kennebunk Free Library and Brick Store Museum are located nearby.

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,009, price is now $722 per person
$722
per person
Apr 18 - Apr 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Maine Mall and Victoria Mansion are located nearby.

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $900, price is now $688 per person
$688
per person
Apr 18 - Apr 24
found 1 day 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 Maine Mall and Fore Street Gallery are located nearby.

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,319, price is now $1,029 per person
$1,029
per person
Apr 18 - Apr 24
found 1 day 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.

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Top Hotel Deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
16.16 km from city center
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 ...
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
16.33 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
15.78 km from city center
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 ...
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St Portland ME
16.25 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
16.02 km from city center
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 ...
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
15.32 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
Old Orchard Beach Inn

Old Orchard Beach Inn

2.5 out of 5
6 Portland Ave Old Orchard Beach ME
33.07 km from city center
Stay at this B&B in Old Orchard Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
433 Fore St Portland ME
15.96 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
209 Fore St Portland ME
15.59 km from city center
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 ...
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
16.24 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Aloft Portland Downtown Waterfront ME

Aloft Portland Downtown Waterfront ME

3 out of 5
379 Commercial Street Portland ME
16.46 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
65 Commercial St Portland ME
15.73 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
1050 Westbrook Street Portland ME
17.33 km from city center
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 ...
LivAway Suites Portland-Scarborough

LivAway Suites Portland-Scarborough

2 out of 5
83 Mussey Rd Scarborough ME
21.34 km from city center
Stay at this hotel in Scarborough. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Maine Mall and Beech Ridge Motor Speedway are located ...
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street Portland ME
16.16 km from city center
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Tue, Jun 9 - Wed, Jun 10
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Jun 9 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Wed, Jun 10, priced at $157 found 1 day ago
Delta
Sun, May 24 - Sat, May 30
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$177 Roundtrip, found 7 hours ago
$177
Roundtrip
found 7 hours ago
Select Delta flight, departing Sun, May 24 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $177 found 7 hours ago
United
Mon, May 4 - Wed, May 13
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$177 Roundtrip, found 4 hours ago
$177
Roundtrip
found 4 hours ago
Select United flight, departing Mon, May 4 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Wed, May 13, priced at $177 found 4 hours ago
American Airlines
Tue, Sep 8 - Fri, Sep 11
LGA
LaGuardia
PWM
Portland Intl. Jetport
$182 Roundtrip, found 7 hours ago
$182
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Sep 8 from LaGuardia to Portland Intl. Jetport, returning Fri, Sep 11, priced at $182 found 7 hours ago
Breeze Airways
Sat, Jun 6 - Sat, Jun 13
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$210 Roundtrip, found 2 hours ago
$210
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Sat, Jun 6 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Jun 13, priced at $210 found 2 hours ago