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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 2 Condo Rentals in Middletown with updated reviews, rates, and availability.

Cozy 2-bedroom condo in charming Stephens City
Property grounds

Cozy 2-bedroom condo in charming Stephens City

10.0 out of 10, Exceptional, (1)
"This was the perfect location for our little get away. We had Easter lunch, played games, and stayed in a very clean nice place!!"
The price is $230
includes taxes & fees
$211 per night
May 2 - May 3
Cozy 2-bedroom condo in charming Stephens City
Historic District Downtown Winchester
Exterior

Historic District Downtown Winchester

9.8 out of 10, Exceptional, (8)
"We love coming here. Great place and great location."
Historic District Downtown Winchester
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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Other property types in Middletown

Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (312)
"very cute little place, would definitely stay again"
Star view cabin-Riverfront
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (83)
"The cabin is beautiful and tucked away in the trees. Amazing colors this time of year and was such a great little getaway. Highly recommend staying here!"
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Falling Leaf Cabin With Winter River And Mountain View!
Exterior

Falling Leaf Cabin With Winter River And Mountain View!

9.8 out of 10, Exceptional, (282)
"Fourth time here and it never gets old!!! absolutely gorgeous!"
Falling Leaf Cabin With Winter River And Mountain View!
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.