Photo by Stephanie Sutton

Search Villas in Middletown

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

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, (86)
"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)
"The rooms were very engaging. My daughter-in-law was charmed. We had lots of indoor places in which to play. The pool in the backyard was great for adults & children during the warm summer!"
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!
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
Elegant Paris Manor w/ Private Pool!
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
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.
Don't see what you're looking for?
See all available properties in Middletown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Middletown

Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (307)
"I recently stayed at this cabin over the weekend, and it was an unforgettable experience. The views were absolutely breathtaking — whether it was sunrise over the mountains or relaxing in the evening with a stunning sunset, the scenery was incredible from every angle.The cabin itself was just as impressive. It was beautifully designed, immaculately clean, and had all the comforts of home. From cozy furniture to thoughtful amenities, everything was perfect. The peaceful surroundings made it the...
Star view cabin-Riverfront
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
2 bedrooms, WiFi, bed sheets

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

9.6 out of 10, Exceptional, (342)
"Amazing view, and very quiet. Exactly what i was looking for. "
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
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, (278)
"We really enjoyed our stay at the Falling Leaf Cabin. It was just what we were looking for. The cabin had a nice log cabin feel and the fire place and hot tub really made it all come together. "
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.

Frequently asked questions

Why book your villa in Middletown with Expedia?
Reserving a villa in Middletown is as simple as entering your travel dates and choosing an option that checks your boxes. Seeking something luxurious or low cost, or a stay that also has a pool and free WiFi? Use Expedia’s search filters to narrow your results and find your perfect match.
How can I find cheap villas in Middletown?
With Expedia’s useful filter tool, reserving cheap villas in Middletown has never been easier. To discover stays that’ll make your wallet happy, narrow your search results by star rating, budget and amenities.