Cumberland Vacation Packages
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Top Holiday Package Deals in Cumberland
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
Price was CA $1,129, price is now CA $678 per person
CA $678
per person
Sep 6 - Sep 13
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
9/10 Wonderful! (3,647 reviews)
The woman at the front desk, I am sorry I didn't get her name, was very very nice.
Reviewed on Jun 29, 2026
The Delaney Hotel
South Orange
Price was CA $1,823, price is now CA $1,154 per person
CA $1,154
per person
Sep 4 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9.6/10 Exceptional! (1,125 reviews)
Despite the location. The stay was peaceful and quiet. the staff was kind. Informative and professional. overall the facility was clean. the room was more than expected. despite the amenities. overall the stay was satisfactory.
Reviewed on Jun 29, 2026
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
Price was CA $1,197, price is now CA $776 per person
CA $776
per person
Aug 31 - Sep 5
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Orlando (MCO)
7.8/10 Good! (518 reviews)
Everything was amazing, since the welcoming until the checkout, highly recommeded
Reviewed on Jun 29, 2026
Westgate Lakes Resort & Spa Universal Studios Area
Price was CA $1,378, price is now CA $896 per person
CA $896
per person
Sep 19 - Sep 25
found 8 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.4/10 Very good! (6,584 reviews)
Will go back there , love everything good
Reviewed on Jun 29, 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Price was CA $2,964, price is now CA $2,003 per person
CA $2,003
per person
Sep 2 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9.2/10 Wonderful! (1,006 reviews)
The home we stayed was super cute, and inside very clean. Pool was a little dirty lots of leaves.
The lady who did my check in was very courteous. I booked for 5 guests but house was accommodated only for 4; So linen must be requested for the sofa bed.
Sofa bed was horrible mattress was old and you could feel the springs.
Aside from all those things grounds are well.kept, clean. Parking was never an issue lots of it.
Reviewed on Jun 28, 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
5/5(1 area review)
If you're spending some time in Downtown Lakeland, Polk Theatre and RP Funding Center are top sights worth seeing.
Cumberland Hotel Deals
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
The price is CA $156 per night from Jul 26 to Jul 27
CA $156
CA $175 total
Jul 26 - Jul 27
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"Parking"
Reviewed on Jun 29, 2026
Comfort Inn & Suites Lakeland North I-4
3520 N Hwy 98 Lakeland FL
Fully refundable
The price is CA $140 per night from Jul 2 to Jul 3
CA $140
CA $157 total
Jul 2 - Jul 3
includes taxes & fees
8.8/10 Excellent! (855 reviews)
"It was easy to check in and check out! Clean rooms will be back!"
Reviewed on Jun 29, 2026
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
The price is CA $486 per night from Jul 12 to Jul 13
CA $486
CA $600 total
Jul 12 - Jul 13
includes taxes & fees
8.8/10 Excellent! (149 reviews)
"Kids love this hotel!"
Reviewed on Jun 26, 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.