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Search results; Over 1,000 homes in Middletown

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Top guest favourite
Home in Middletown
5Bdrm Estate/Tennis near LegoLand
5 bedrooms, 7 beds, 2.5 private bathrooms
1–6 Oct
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4.97 out of 5 average rating, 72 reviews
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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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Home in Middletown
Peace and quiet. Comfy, private house to relax in
4 bedrooms, 4 beds, 1.5 bathrooms
9–14 Nov
4.98 out of 5 average rating, 224 reviews
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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
1–6 Oct
4.71 out of 5 average rating, 7 reviews
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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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Room in Hamptonburgh
Hudson Haven, Blue Room
2 beds, 2 bathrooms
11–16 Oct
4.96 out of 5 average rating, 23 reviews
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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
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 Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.96 out of 5 average rating, 436 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, 189 reviews
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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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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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Flat in Newburgh
The Hudson View Retreat.
2 bedrooms, 2 queen beds, 1.5 bathrooms
18–23 Oct
New place to stay
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Guest suite in Goshen
Private Guest Suite at Hudson Valley Happy Place!
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 334 reviews
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Top guest favourite
Flat in Montgomery
Hudson Valley Modern Apartment. King Bed/Queen
1 bedroom, 3 beds, 1 bathroom
24–29 Oct
4.97 out of 5 average rating, 79 reviews
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Room in Matamoras
Spacious Private Room with 2 Queen Beds &Bathroom
1 bed, 1 bathroom
1–6 Oct
New place to stay
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Home in Montgomery
Cozy Montgomery Home
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Dec
New place to stay