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Search results; Over 1,000 homes in Middletown

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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 private bathrooms
9–14 Nov
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4.98 out of 5 average rating, 224 reviews
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Top guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #202
1 queen bed, 1 bathroom
25–30 Oct
4.95 out of 5 average rating, 42 reviews
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Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
2 beds, 1 bathroom
11–16 Oct
4.95 out of 5 average rating, 19 reviews
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Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds, 3.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 21 reviews
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Home in Otisville
3BedRM Cozy Home Otisville Middletown Deer Park
3 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.71 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Middletown
Private Secret Escape • Hot Tub • Pool • Fire Pit
4 bedrooms, 8 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Middletown
5Bdrm Estate/Tennis near LegoLand
5 bedrooms, 7 beds, 2.5 bathrooms
1–6 Oct
4.97 out of 5 average rating, 72 reviews
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Chalet in Warwick
Mountain View Retreat w/ Hot Tub, Theater, and Gym
4 bedrooms, 5 beds, 3.5 bathrooms
2–7 Oct
4.99 out of 5 average rating, 190 reviews
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Top guest favourite
Villa in Goshen
Spectacular Historic Mansion w/Pool&Tennis
10 bedrooms, 17 beds, 5.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 44 reviews
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Home in Monroe
Spacious 4BR • Warwick • Hiking Trails & Lake
5 bedrooms, 7 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Montgomery
Cozy studio apartment with everything you need!
1 queen bed, 1 bathroom
4–9 Oct
4.96 out of 5 average rating, 24 reviews
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Guest favourite
Home in Slate Hill
The Wooden Igloo Near Legoland NY
4 bedrooms, 7 beds, 3.5 bathrooms
18–23 Oct
4.96 out of 5 average rating, 28 reviews
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Guest favourite
Room in Slate Hill
Stone Oak Tree Farm Canaan Fir Room
1 queen bed, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 112 reviews
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Top guest favourite
Cottage in Newburgh
Cozy Lake Cottage
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.88 out of 5 average rating, 261 reviews
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Guest favourite
Villa in Bloomingburg
Spacious 6BR Villa | Serene Scenic Mountain Escape
6 bedrooms, 11 beds, 3 bathrooms
11–16 Oct
4.87 out of 5 average rating, 118 reviews
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Guest favourite
Flat in Newburgh
Special Nest w Private Entrance River View Porches
1 bedroom, 1 queen bed, 2 bathrooms
27 Nov – 2 Dec
4.88 out of 5 average rating, 280 reviews
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Guest favourite
Barn in Middletown
The Elm Barn- long term OK
2 bedrooms, 4 beds, 3 bathrooms
17–22 Oct
4.79 out of 5 average rating, 99 reviews
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Top guest favourite
Room in Hamptonburgh
Hudson Haven, Master Suite
1 king bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Room in Hamptonburgh
Hudson Haven, Blue Room
2 beds, 2 bathrooms
11–16 Oct
4.96 out of 5 average rating, 23 reviews