Middleton Vacation Packages

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Top Middleton Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Palazzo Lakeside Hotel

CA $591

per person

Oct 20 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Orlando (MCO)

8.4/10 Very good! (5,255 reviews)

Clean modern room.

Reviewed on Aug 11, 2026

Westgate Palace Hotel / Universal / I-Drive

International Drive District

CA $760

per person

Sep 27 - Oct 2

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Orlando (MCO)

9/10 Wonderful! (1,304 reviews)

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

CA $784

per person

Sep 13 - Sep 19

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Orlando (MCO)

7.8/10 Good! (564 reviews)

Reviewed on Aug 9, 2026

Westgate Vacation Villas Resort

CA $604

per person

Oct 20 - Oct 25

found 22 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Orlando (MCO)

8.2/10 Very good! (2,028 reviews)

Nothinh...................

Reviewed on Aug 11, 2026

The Delaney Hotel

South Orange

CA $1,016

per person

Oct 20 - Oct 25

found 16 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Orlando (MCO)

9.6/10 Exceptional! (1,178 reviews)

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Middleton Hotel Deals

The Waterfront Inn

1105 Lake Shore Drive The Villages FL

CA $152

CA $163 total

Sep 1 - Sep 2

includes taxes & fees

9.2/10 Wonderful! (1,476 reviews)

"The hotel was clean and updated. Comfortable beds. Great lake view at hotel bar/restaurant. Staff was friendly and helpful. Excellent location a block from Sumtner Square with music , shopping and bars. Would stay here again. Highly recommend."

Reviewed on Aug 10, 2026

Brownwood Hotel & Spa

3003 Brownwood Blvd Wildwood FL

Fully refundableReserve now, pay when you stay

CA $156

CA $167 total

Aug 25 - Aug 26

includes taxes & fees

Hotel Eastport

7065 Beebe Court Wildwood FL

Fully refundableReserve now, pay when you stay

CA $161

CA $172 total

Aug 20 - Aug 21

includes taxes & fees

9.6/10 Exceptional! (255 reviews)

"Hundreds of spiders everywhere plus roaches. $344 per room that should have been $225 in terms of construction and functionality."

Reviewed on Aug 9, 2026

See all 2,246 properties in Middleton

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.