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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 6 Villas in Middletown with updated reviews, rates, and availability.

Westcott House- Privacy, amenities and space all in one beautiful package!
Property grounds

Westcott House- Privacy, amenities and space all in one beautiful package!

9.8 out of 10, Exceptional, (88)
"A group of 25 teachers gathered to enjoy professional development and relaxation at the Westcott House. We had a wonderful time relaxing in all of the cozy spots and enjoying the pretty views of the fall leaves. We were glad to see the deck boards replaced from our visit two years ago. Our only complaint this time is how many stubbed toes we went home with from the raised bath mats! The property is wonderful and we hope to return again!"
Westcott House- Privacy, amenities and space all in one beautiful package!
Historic Virginia Wine Country Villa w/ Pool, Yard
Outdoor dining

Historic Virginia Wine Country Villa w/ Pool, Yard

7.6 out of 10, Good, (15)
"We had a great family vacation, everyone lived the pool!!"
Historic Virginia Wine Country Villa w/ Pool, Yard
Elegant Paris Manor w/ Private Pool!
Property grounds

Elegant Paris Manor w/ Private Pool!

10.0 out of 10, Exceptional, (1)
"Wonderful property with wonderful people. The Manor house is incredible. The pool and the outdoor space was exactly what we had hoped for. Everyone really enjoyed the wagon ride to the top of the property. Definitely would recommend this family or just a getaway for 2 on a weekend!! John"
Elegant Paris Manor w/ Private Pool!
Elegant Paris Manor w/ Private Pool!
Interior

Elegant Paris Manor w/ Private Pool!

3.0 star property
Elegant Paris Manor w/ Private Pool!
Historic Virginia Wine Country Villa w/ Pool, Yard
Outdoor dining

Historic Virginia Wine Country Villa w/ Pool, Yard

3.0 star property
Historic Virginia Wine Country Villa w/ Pool, Yard
Private Indoor W/ Pool-WiFi-Aracde-Fire Pit-Mountain Views
Interior

Private Indoor W/ Pool-WiFi-Aracde-Fire Pit-Mountain Views

Private Indoor W/ Pool-WiFi-Aracde-Fire Pit-Mountain Views
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

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)
"Beautiful location and home"
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (313)
"very cute little place, would definitely stay again"
Star view cabin-Riverfront
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
2 bedrooms, WiFi, bed sheets

Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

9.6 out of 10, Exceptional, (312)
"Beautiful view, really nice wood burning fireplace, clean and cozy. Nice accommodations. Rustic in appearance and feel, with modern amenities."
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
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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