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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
9–14 Aug
4.96 out of 5 average rating, 28 reviews
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
2 beds
3–8 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Middletown
Peace and quiet. Comfy, private house to relax in
4 bedrooms, 4 beds
7–12 Sept
4.98 out of 5 average rating, 218 reviews
Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds
10–15 Aug
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Goshen
Goshen Village Home
2 bedrooms, 2 queen beds
10–15 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Barn in Montgomery
16taft
2 queen beds
9–14 Aug
4.98 out of 5 average rating, 42 reviews
Luxe
Villa in Middletown
Pinnacle Pointe | Year-Round Pool Spa Lake Theater
7 bedrooms, 12 beds
31 Aug – 5 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Home in Warwick
Deer Pond Lodge Lawn Games Hot Tub Game Room 1Pet
4 bedrooms, 5 beds
9–14 Aug
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Home in Goshen
Cozy Brookside Cottage on the Farm
1 bedroom, 2 beds
7–12 Sept
4.94 out of 5 average rating, 95 reviews
Guest favourite
Cabin in Wurtsboro
Forest Spa Retreat on Cascading Brook • 90 Min NYC
3 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 447 reviews
Top guest favourite
Flat in Goshen
Carriage House Apartment Close to Legoland NY
3 bedrooms, 4 beds
3–8 Aug
4.97 out of 5 average rating, 121 reviews
Guest favourite
Cabin in Ellenville
Catskills Cabin, Hot Tub, Wood Stove, King Bed
2 bedrooms, 3 beds
16–21 Aug
4.98 out of 5 average rating, 223 reviews
Top guest favourite
Flat in Montgomery
Cozy studio apartment with everything you need!
1 queen bed
16–21 Aug
4.95 out of 5 average rating, 22 reviews
Guest favourite
Chalet in Wurtsboro
Gorgeous Chalet with Lots of Room!
2 bedrooms, 3 beds
9–14 Aug
4.96 out of 5 average rating, 246 reviews
Guest favourite
Cottage in Pine Bush
Modern 3BR BoHo Retreat/Nearby Hiking, Wineries
3 bedrooms, 3 queen beds
15–20 Aug
4.95 out of 5 average rating, 130 reviews
Flat in Middletown
The Columbus Hotel | The Residence Studio | 89-206
1 double bed
3–8 Aug
New place to stay
Top guest favourite
Farm stay in Goshen
Bright Farm House- Tranquil setting
3 bedrooms, 5 beds
26 Sept – 1 Oct
4.89 out of 5 average rating, 409 reviews
Home in Otisville
3BedRM Cozy Home Otisville Middletown Deer Park
3 bedrooms, 3 beds
19–24 Aug
4.75 out of 5 average rating, 4 reviews