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Search results; Over 1,000 homes in Middletown

Hotel in Middletown
Wayside Inn (Room #15) Bernstein Suite
1 bedroom, 1 bed, 1 private bathroom
15–20 Sept
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4.75 out of 5 average rating, 4 reviews
Hotel in Middletown
Wayside Inn (Room #18 ) Shenandoah Guest
1 bedroom, 1 bed, 1 bathroom
15–20 Sept
4.68 out of 5 average rating, 31 reviews
Top guest favourite
Religious building in Stephens City
The Sanctuary in the Shenandoah Valley
3 bedrooms, 6 beds, 2 bathrooms
21–26 Sept
4.96 out of 5 average rating, 136 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
4.98 out of 5 average rating, 57 reviews
Superhost
Home in Strasburg
Cedar Creek Wayside Castle
4 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
4.76 out of 5 average rating, 306 reviews
Guest favourite
Home in Stephens City
The Happy Farmhouse
3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
4.93 out of 5 average rating, 14 reviews
Guest favourite
Home in Stephens City
Seven Oaks Large Gathering Recreation Paradise
4 bedrooms, 6 beds, 2.5 bathrooms
15–20 Sept
4.99 out of 5 average rating, 82 reviews
Superhost
Home in Middletown
Cozy Reliance Retreat with Beautiful Views
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
4.9 out of 5 average rating, 157 reviews
Top guest favourite
Home in Strasburg
Shenandoah Fort Valley Mountain Retreat*Whole Home
3 bedrooms, 6 beds, 3 bathrooms
26–31 Oct
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Home in Strasburg
"Shenandoah View"
5 bedrooms, 6 beds, 2.5 bathrooms
15–20 Sept
4.97 out of 5 average rating, 33 reviews
Superhost
Home in Front Royal
Trailside Retreat w/ Hot Tub, Sauna, Fireplace
4 bedrooms, 4 queen beds, 4 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Home in Front Royal
The Royal Cabin | 6BR Getaway w/ Hot Tub
6 bedrooms, 7 beds, 4 bathrooms
15–20 Sept
4.97 out of 5 average rating, 187 reviews
Guest favourite
Home in Front Royal
Eclectic LogCabin HotTub, Sauna steps from Trail
4 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.97 out of 5 average rating, 359 reviews
Top guest favourite
Home in Front Royal
Big bright 4 br 2 ba house in town walk to Main St
4 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
4.97 out of 5 average rating, 134 reviews
Guest favourite
Home in Front Royal
3br/1ba house up to 6 people
3 bedrooms, 5 beds, 1 bathroom
28 Sept – 3 Oct
4.91 out of 5 average rating, 121 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 249 reviews
Top guest favourite
Cabin in Stephens City
Chalet w/Hot Tub, Deck, Game Room & EV Charger
3 bedrooms, 3 beds, 2 bathrooms
2–7 Oct
4.91 out of 5 average rating, 32 reviews
Top guest favourite
Tiny home in Stephens City
Farm Stay in a luxury tiny home with hot tub
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 168 reviews