Photo by Stephanie Sutton

Search Middletown Villa Rentals from CA $682

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26

Browse Select Middletown Villas

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, (90)
"This was just what we needed. We had a family of 30. Included were teens that enjoyed having a separate space and pool table. The upstairs main room was so spacious and the tables were set up like a restaurant. Perfect for meals and mingling. The kitchen was well stocked for cooking meals. We would stay here again. "
Westcott House- Privacy, amenities and space all in one beautiful package!
Events and Concierge! 6BR Heated Pool Near Wineries
TV, fireplace, DVD player, stereo

Events and Concierge! 6BR Heated Pool Near Wineries

The price is CA $682
CA $2,092 total
includes taxes & fees
Sep 1 - Sep 2
Events and Concierge! 6BR Heated Pool Near Wineries
Historic Virginia Wine Country Villa w/ Pool, Yard
Villa (6 Bedrooms) | Interior

Historic Virginia Wine Country Villa w/ Pool, Yard

3.0 star property
Historic Virginia Wine Country Villa w/ Pool, Yard
Elegant Paris Manor w/ Private Pool!
Villa (6 Bedrooms) | Interior

Elegant Paris Manor w/ Private Pool!

3.0 star property
Elegant Paris Manor w/ Private Pool!
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
Será - Villa 2 - Prebook Now for Prelaunch Rates!
Property grounds

Será - Villa 2 - Prebook Now for Prelaunch Rates!

Será - Villa 2 - Prebook Now for Prelaunch Rates!
Será - Villa 1 - Book Now for Prelaunch Rates!!!
Exterior

Será - Villa 1 - Book Now for Prelaunch Rates!!!

Será - Villa 1 - Book Now for Prelaunch Rates!!!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Find out more about Middletown

Find out more about Middletown

Middletown Villas information

Number of reviews
50
Accommodation
7 Villas
Lowest Price
CA $682
Highest Price
CA $682

Explore a world of travel with Expedia

Explore a world of travel with Expedia