Cumberland Vacation Packages
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Top Holiday Package Deals in Cumberland
Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel
Sunshine Beach
CA $1,246
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,128 reviews)
We absolutely loved the entire stay, it was by far the best hotel with a fully equipped kitchen, double separate bedrooms, double bathrooms, the service was on top, close to the beach. Everything was superior, would not change a thing! Will definitely return next year!
Reviewed on Aug 15, 2026
Where to stay in Cumberland
Find the best Cumberland areas and neighborhoods for the activities you enjoy most. Learn more about Cumberland
Downtown Lakeland
2 out of top 10 points of interest in this area
If you're spending some time in Downtown Lakeland, RP Funding Center and Lake Mirror are top sights worth seeing.
Lake Hollingsworth
If you're spending some time in Lake Hollingsworth, Lake Hollingsworth and Veterans Park are top sights worth seeing.
Lakeland Highlands
When in Lakeland Highlands, you can plan a visit to Family Fun Center and The Club at Eaglebrooke, some noteworthy sights in the nearby area.
South Lake Morton
1 out of top 10 points of interest in this area
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 RP Funding Center.
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 Theatre.
Cumberland Hotel Deals
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundableReserve now, pay when you stay
CA $121
CA $136 total
Sep 13 - Sep 14
includes taxes & fees
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
CA $256
CA $286 total
Aug 28 - Aug 29
includes taxes & fees
8.6/10 Excellent! (179 reviews)
"Great customer service!"
Reviewed on Aug 9, 2026
Days Inn & Suites by Wyndham Lakeland
4502 N Socrum Loop Rd Lakeland FL
Fully refundableReserve now, pay when you stay
CA $82
CA $101 total
Aug 16 - Aug 17
includes taxes & fees
8.6/10 Excellent! (438 reviews)
"There was a bug in my room. I was unable to charge my cell phone, the outlets did not work. The breakfast was minimal, would like the convenience of preparing coffee in room, have disabilities"
Reviewed on Aug 15, 2026
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.
Things to do
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.