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Search results; Over 1,000 homes in Middletown

Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #202
1 queen bed
13–18 Sept
4.97 out of 5 average rating, 35 reviews
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
2 beds
13–18 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds
15–20 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Middletown
Peace and quiet. Comfy, private house to relax in
4 bedrooms, 4 beds
9–14 Nov
4.98 out of 5 average rating, 223 reviews
Home in Middletown
Private Secret Escape • Hot Tub • Pool • Fire Pit
4 bedrooms, 8 beds
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Home in Otisville
3BedRM Cozy Home Otisville Middletown Deer Park
3 bedrooms, 3 beds
12–17 Sept
4.71 out of 5 average rating, 7 reviews
Top guest favourite
Home in Middletown
5Bdrm Estate/Tennis near LegoLand
5 bedrooms, 7 beds
8–13 Sept
4.97 out of 5 average rating, 71 reviews
Luxe
Villa in Middletown
Pinnacle Pointe | Year-Round Pool Spa Lake Theater
7 bedrooms, 12 beds
8–13 Sept
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Chalet in Warwick
Mountain View Retreat w/ Hot Tub, Theater, and Gym
4 bedrooms, 5 beds
13–18 Sept
4.99 out of 5 average rating, 186 reviews
Top guest favourite
Home in Goshen
Goshen Village Home
2 bedrooms, 2 queen beds
1–6 Apr
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Glen Wild
3BR Catskills Getaway Retreat!
3 bedrooms, 5 beds
20–25 Sept
4.98 out of 5 average rating, 50 reviews
Top guest favourite
Villa in Goshen
Goshen Retreat w/ Hot Tub & Pool near Legoland
5 bedrooms, 7 beds
13–18 Sept
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
2 bedrooms, 2 beds
4–9 Nov
4.92 out of 5 average rating, 347 reviews
Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds
13–18 Sept
4.96 out of 5 average rating, 434 reviews
Top guest favourite
Flat in Montgomery
Hudson Valley Modern Apartment. King Bed/Queen
1 bedroom, 3 beds
20–25 Sept
4.97 out of 5 average rating, 76 reviews
Guest favourite
Home in Chester
Serene Private Home • Light-Filled • Hot Tub •Deck
4 bedrooms, 8 beds
11–16 Sept
4.92 out of 5 average rating, 169 reviews
Home in Port Jervis
The Grazing Acres Getaway by Echo Fields
3 bedrooms, 3 queen beds
13–18 Sept
New place to stay
Guest favourite
Barn in Wurtsboro
Catskills Barn Retreat w/Fireplace & 9 Acres
4 bedrooms, 8 beds
13–18 Sept
4.94 out of 5 average rating, 131 reviews