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Search results; Over 1,000 homes in Middletown

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Guest favourite
Home in Middletown
Cozy Reliance Retreat with Beautiful Views
1 bedroom, 2 beds, 1 private bathroom
7–12 Sept
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4.9 out of 5 average rating, 155 reviews
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Top guest favourite
Tiny home in Stephens City
Farm Stay in a luxury tiny home with hot tub
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 160 reviews
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Hotel in Middletown
Wayside Inn (Room #18 ) Shenandoah Guest
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.68 out of 5 average rating, 31 reviews
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Guest favourite
Home in Middletown
Family Suite at Wayside Inn
3 bedrooms, 3 beds, No bathroom
1–6 Jan
4.81 out of 5 average rating, 36 reviews
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Guest favourite
Cabin in Stephens City
Chalet w/Hot Tub, Deck, Game Room & EV Charger
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.9 out of 5 average rating, 30 reviews
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Top guest favourite
Home in Strasburg
Shenandoah Fort Valley Mountain Retreat*Whole Home
3 bedrooms, 6 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 44 reviews
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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
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Home in Front Royal
The Tree House on the River- sleeps 4, dog allowed
1 bedroom, 2 queen beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 93 reviews
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Guest suite in Front Royal
Chapel View Nest: Patio, Firepit and Views.
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 162 reviews
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Top guest favourite
Religious building in Stephens City
The Sanctuary in the Shenandoah Valley
3 bedrooms, 6 beds, 2 bathrooms
7–12 Sept
4.96 out of 5 average rating, 136 reviews
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Guest favourite
Home in Stephens City
The Happy Farmhouse
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
4.92 out of 5 average rating, 13 reviews
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Home in Front Royal
Mountain View Bungalow
1 bedroom, 1 bed, 1 bathroom
15–20 Sept
4.98 out of 5 average rating, 44 reviews
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Guest house in Middletown
Riverfront Oasis with Mountain Views, Near Town
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.9 out of 5 average rating, 48 reviews
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Home in Strasburg
Teaberry Hill - “Million dollar view”
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 27 reviews
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Holiday home in Front Royal
Shenandoah Riverfront Cottage! Hot Tub! Sleeps 4!
2 bedrooms, 2 beds, 1 bathroom
24–29 Oct
4.96 out of 5 average rating, 171 reviews
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Home in Maurertown
Comfy 3-bedroom country house
3 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 133 reviews
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Place to stay in Strasburg
NASH Vintage Garage Getaway
2 bedrooms, 5 beds, 1 bathroom
1–6 Sept
4.99 out of 5 average rating, 87 reviews
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Home in Winchester
City Charmer minutes from Old Town
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
4.97 out of 5 average rating, 294 reviews
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Flat in Winchester
Newly repurposed Historic Home in Winchester VA!
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.9 out of 5 average rating, 143 reviews