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Search results; Over 1,000 homes in Middletown

Hotel in Middletown
Wayside Inn (Room #3) Cedar Creek Guest Room
1 bedroom, 1 bed, 1 private bathroom
14–19 Sept
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4.75 out of 5 average rating, 4 reviews
Top guest favourite
Tiny home in Stephens City
Farm Stay in a luxury tiny home with hot tub
1 bedroom, 2 beds
25–30 Oct
5.0 out of 5 average rating, 167 reviews
Hotel in Middletown
Wayside Inn (Room #18 ) Shenandoah Guest
1 bedroom, 1 bed
14–19 Sept
4.68 out of 5 average rating, 31 reviews
Guest favourite
Home in Stephens City
Seven Oaks Large Gathering Recreation Paradise
4 bedrooms, 6 beds
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
11–16 Oct
4.9 out of 5 average rating, 157 reviews
Guest favourite
Cabin in Stephens City
Chalet w/Hot Tub, Deck, Game Room & EV Charger
3 bedrooms, 3 beds
20–25 Sept
4.91 out of 5 average rating, 32 reviews
Superhost
Cabin in Front Royal
Whispering Tides River Cabin | *Skyline, Vineyards
2 bedrooms, 2 beds
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Strasburg
Mint House Cottage
2 bedrooms, 3 beds
22–27 Sept
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Home in Strasburg
Shenandoah Fort Valley Mountain Retreat*Whole Home
3 bedrooms, 6 beds
26–31 Oct
5.0 out of 5 average rating, 44 reviews
Guest favourite
Holiday home in Front Royal
Shenandoah Riverfront Cottage! Hot Tub! Sleeps 4!
2 bedrooms, 2 beds
8–13 Nov
4.97 out of 5 average rating, 174 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 163 reviews
Guest favourite
Home in Winchester
City Charmer minutes from Old Town
2 bedrooms, 2 beds
11–16 Oct
4.97 out of 5 average rating, 294 reviews
Townhouse in Winchester
Modern Mid-Century Townhome w Deck near festivals
3 bedrooms, 3 beds
1–6 Nov
4.58 out of 5 average rating, 12 reviews
Top guest favourite
Room in Stephens City
Room in Quiet Neighborhood
1 double bed
23–28 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Home in Star Tannery
Scenic Mountain Side House to Unplug
4 bedrooms, 5 beds
15–20 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Religious building in Stephens City
The Sanctuary in the Shenandoah Valley
3 bedrooms, 6 beds
21–26 Sept
4.96 out of 5 average rating, 136 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds
14–19 Sept
4.98 out of 5 average rating, 57 reviews
Guest favourite
Home in Middletown
Mountain View Moto Retreat
2 bedrooms, 3 beds
1–6 Dec
4.91 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds
26 Sept – 1 Oct
4.97 out of 5 average rating, 359 reviews