Cleveland Vacations from $1,069

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Your Cleveland Vacation

See and do more with a Cleveland vacation package. Whether you're going for the watersports, walking trails, nature, or something else, our package deals make travel planning hassle-free. A trip to Cleveland wouldn't be complete without spending a bit of time in Middlesbrough. This city is among the leading places to visit here. If you're ready to stop dreaming and start packing, Expedia will help turn your Cleveland vacation into reality.

The Latest Cleveland vacation packages

Price found within the past 48 hours. Click for updated prices.
North Lakes Hotel And Spa
Marshall Meadows Manor House
Windermere Manor Hotel
Keswick Country House Hotel
Low Wood Bay Resort & Spa
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Cleveland Hotel Deals

Parkmore Hotel & Leisure Club, Sure Hotel Collection by BW

Parkmore Hotel & Leisure Club, Sure Hotel Collection by BW

3.5 out of 5
636 Yarm Road, Eaglescliffe, Stockton-on-Tees, England
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $135 total per night from Aug 24 to Aug 25
$135 total
Aug 24 - Aug 25
Total includes taxes and fees
7.6/10 Good! (414 reviews)
Great weekend break
"Had a lovely, stay Clean, comfortable & friendly place"

Reviewed on May 25, 2025

Parkmore Hotel & Leisure Club, Sure Hotel Collection by BW
Gisborough Hall

Gisborough Hall

4 out of 5
Whitby Lane, Guisborough, England
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (584 reviews)
"Beautiful place"

Reviewed on Aug 9, 2025

Gisborough Hall
Cross Keys Hotel by Greene King Inns

Cross Keys Hotel by Greene King Inns

3 out of 5
Middlesborough Rd, Guisborough, England
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $101 total per night from Aug 29 to Aug 30
$101 total
Aug 29 - Aug 30
Total includes taxes and fees
8.2/10 Very Good! (418 reviews)
"C"

Reviewed on Aug 18, 2025

Cross Keys Hotel by Greene King Inns
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.