Photo by Stephanie Sutton
Search Vacation Homes in Middletown
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 184 Vacation Homes in Middletown with updated reviews, rates, and availability.

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
9.6 out of 10, Exceptional, (173)

Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
9.8 out of 10, Exceptional, (28)

Secluded River Cabin Getaway (Masten Cabin)
Secluded River Cabin Getaway (Masten Cabin)
9.8 out of 10, Exceptional, (145)

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
9.8 out of 10, Exceptional, (47)

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (214)

Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
10.0 out of 10, Exceptional, (44)

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (176)

Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery
Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery
9.8 out of 10, Exceptional, (47)
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
Other property types in Middletown

Star view cabin-Riverfront
Star view cabin-Riverfront
9.8 out of 10, Exceptional, (307)

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
9.6 out of 10, Exceptional, (343)

Falling Leaf Cabin With Winter River And Mountain View!
Falling Leaf Cabin With Winter River And Mountain View!
9.8 out of 10, Exceptional, (279)
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.
Recent reviews of Middletown hotels
Recent reviews of Middletown hotels

La Quinta Inn & Suites by Wyndham Winchester
5/5 Excellent
"The hotel was easy access, clean and a good value for the price. The room was very modern and had everything needed for an overnight stay. "
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Winchester
Posted 2 days ago