Cumberland Vacation Packages

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The Latest Cumberland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel with a central pool area, multiple swimming pools, and a waterfront location.
    Feb 3 - Feb 8

    Westgate Town Center Resort + Flight

    Kissimmee
    5 nights
    4.0 star property
    8.4/10 - Very good (2,082 reviews)
    "I always stay at this resort when I travel to Orlando with my family. I highly recommend!"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    CA $1,172
    CA $653
    per traveller
    found 1 day ago
    Westgate Town Center Resort
  • A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a clear sky.
    Dec 18 - Dec 23

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Hamilton (YHM) - Orlando (MCO)
    YHM - MCO • Nonstop MCO - YHM • Nonstop
    Save 100% on your flight
    CA $2,415
    CA $1,358
    per traveller
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • A modern kitchen with a large island, white cabinetry, and a view of the beach.
    Feb 2 - Feb 7

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    5 nights
    4.0 star property
    9.6/10 - Exceptional (1,325 reviews)
    "Nice property, clean pool. Units were not sound roof at all, you could hear every little noise from each room and other units, but it did not ruin our time there."
    Reviewed November 10, 2026
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $2,846
    CA $1,618
    per traveller
    found 1 day ago
    Ocean Club Treasure Island Hotel
  • A deck with lounge chairs and tables overlooking a beach with palm trees and ocean waves.
    Jan 24 - Jan 28

    Westgate Cocoa Beach Resort + Flight

    Cocoa Beach
    4 nights
    4.0 star property
    8.6/10 - Excellent (579 reviews)
    "nice property close to the ocean no views from room. Staff was friendly except for beach chair and umbrella guyHe would not permit us to use paid for equipment given to us by another resident."
    Reviewed November 10, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    CA $1,717
    CA $981
    per traveller
    found 1 day ago
    Westgate Cocoa Beach Resort
  • A hotel with a central pool area, multiple water slides, and a surrounding pool.
    Dec 18 - Dec 23

    Westgate Vacation Villas Resort + Flight

    Kissimmee
    5 nights
    4.0 star property
    8.2/10 - Very good (2,136 reviews)
    "Good place"
    Reviewed November 9, 2026
    Roundtrip • Hamilton (YHM) - Orlando (MCO)
    YHM - MCO • Nonstop MCO - YHM • Nonstop
    CA $1,463
    CA $912
    per traveller
    found 21 hours ago
    Westgate Vacation Villas Resort

Where to stay in Cumberland

Find the best Cumberland areas and neighborhoods for the activities you enjoy most. Learn more about Cumberland
Learn more about Cumberland
A sunset over a body of water with a park and a distant city skyline.
Photo by Rachel Graves
Open Photo by Rachel Graves

Downtown Lakeland

If you're spending some time in Downtown Lakeland, Polk Theatre and RP Funding Center are top sights worth seeing.
A garden with a central fountain, surrounded by white columns and covered walkways.

Lake Hollingsworth

If you're spending some time in Lake Hollingsworth, Lake Hollingsworth and Beerman Family Tennis Center are top sights worth seeing.
A crocodile resting on a log near a body of water with greenery around.

Lakeland Highlands

When in Lakeland Highlands, you can plan a visit to The Club at Eaglebrooke and Family Fun Center, some noteworthy sights in the nearby area.
A circular fountain with a statue in the center, surrounded by palm trees and a building with a red roof in the background.

South Lake Morton

If you're looking for some top things to see and do in South Lake Morton and surrounding area, you can visit Lake Mirror and Polk Theatre.
A wooden boardwalk by a lake with trees and a bench.

Dixieland

While there might not be top attractions in Dixieland, you can explore the larger area and discover places like RP Funding Center and Polk Museum of Art.

Cumberland Hotel Deals

A modern kitchen area with a central island, bar stools, and a seating area with a sofa and chairs.

Hampton Inn & Suites Lakeland-South Polk Parkway

Hampton Inn & Suites Lakeland-South Polk Parkway
2.5 star property
5.2 km from Cumberland
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean Room."
The price is CA $167
CA $187 total
includes taxes & fees
Nov 27 - Nov 28
Hampton Inn & Suites Lakeland-South Polk Parkway
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.
See all properties in Cumberland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.