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Search results; Over 1,000 homes in Middletown

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Superhost
Tent in Middletown
9 person glamping tent- White owl
1 bedroom, 8 beds, 1 bathroom
6–11 Sept
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5.0 out of 5 average rating, 4 reviews
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Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #202
1 queen bed, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 33 reviews
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Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
2 beds, 1 bathroom
6–11 Sept
4.92 out of 5 average rating, 13 reviews
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Superhost
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds, 3.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Middletown
Peace and quiet. Comfy, private house to relax in
4 bedrooms, 4 beds, 1.5 bathrooms
12–17 Oct
4.98 out of 5 average rating, 218 reviews
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Home in Otisville
3BedRM Cozy Home Otisville Middletown Deer Park
3 bedrooms, 3 beds, 1 bathroom
12–17 Sept
4.67 out of 5 average rating, 6 reviews
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Home in Middletown
Secret Escape Hot tub • Pool • Private Location
4 bedrooms, 8 beds, 2.5 bathrooms
7–13 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Middletown
5Bdrm Estate/Tennis near LegoLand
5 bedrooms, 7 beds, 2.5 bathrooms
7–12 Sept
4.97 out of 5 average rating, 70 reviews
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Luxe
Villa in Middletown
Pinnacle Pointe | Year-Round Pool Spa Lake Theater
7 bedrooms, 12 beds, 8 bathrooms
1–6 Sept
4.91 out of 5 average rating, 11 reviews
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Top guest favourite
Barn in Montgomery
16taft
2 queen beds, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 43 reviews
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Superhost
Home in Woodridge
Hotel Buyout | 54 Guests | Belvedere Suites
18 bedrooms, 45 beds, 18 bathrooms
1–6 Sept
New place to stay
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Top guest favourite
Home in Chester
The Little Green Farmhouse
4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 163 reviews
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Top guest favourite
Home in Glen Wild
3BR Catskills Getaway Retreat!
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 49 reviews
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Guest favourite
Barn in Wurtsboro
Catskills Barn Retreat w/Fireplace & 9 Acres
4 bedrooms, 8 beds, 2.5 bathrooms
6–11 Sept
4.94 out of 5 average rating, 130 reviews
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Guest favourite
Cottage in Pine Bush
Modern 3BR BoHo Retreat/Nearby Hiking, Wineries
3 bedrooms, 3 queen beds, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 133 reviews
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Top guest favourite
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 341 reviews
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Home in Port Jervis
The Grazing Acres Getaway by Echo Fields
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Sept
New place to stay
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Guest favourite
Home in Slate Hill
The Wooden Igloo Near Legoland NY
6 bedrooms, 7 beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Chalet in Warwick
Mountain View Retreat w/ Hot Tub, Theater, and Gym
4 bedrooms, 5 beds, 3.5 bathrooms
7–12 Sept
4.99 out of 5 average rating, 186 reviews