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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, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 37 reviews
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
2 beds, 1 bathroom
27 Sept – 2 Oct
4.94 out of 5 average rating, 17 reviews
Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds, 3.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Barn in Montgomery
16taft
2 queen beds, 1 bathroom
19–24 Sept
4.98 out of 5 average rating, 44 reviews
Luxe
Villa in Middletown
Pinnacle Pointe | Year-Round Pool Spa Lake Theater
7 bedrooms, 12 beds, 8 bathrooms
18–23 Sept
4.92 out of 5 average rating, 12 reviews
Guest favourite
Flat in Newburgh
Special Nest w Private Entrance River View Porches
1 bedroom, 1 queen bed, 2 bathrooms
27 Nov – 2 Dec
4.89 out of 5 average rating, 279 reviews
Home in Montgomery
Walk to Village! 5BR Home, 2 Kitchens, King Beds
6 bedrooms, 8 beds, 4.5 bathrooms
22–27 Oct
Top guest favourite
Rooms in Goshen
Parkway House Goshen Bed & Breakfast Suite #2
2 bedrooms, 4 beds, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Goshen
Unique Dutch Barn in the Hudson Valley
5 bedrooms, 9 beds, 3 bathrooms
20–25 Sept
4.97 out of 5 average rating, 116 reviews
Top guest favourite
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
Guest favourite
Home in Montgomery
The Ferns at Winding Hills
4 bedrooms, 5 beds, 4 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Montgomery
Hudson Valley Home with Pool & Jacuzzi
3 bedrooms, 4 beds, 2.5 bathrooms
14–19 Sept
4.94 out of 5 average rating, 82 reviews
Home in Montgomery
Cozy Montgomery Home
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Dec
New place to stay
Top guest favourite
Home in Montgomery
The B House
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Room in Hamptonburgh
Hudson Haven, Master Suite
1 king bed, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Woodridge
Hotel Buyout | 54 Guests | Belvedere Suites
18 bedrooms, 45 beds, 18 bathrooms
18–23 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Farm stay in Middletown
Hudson Valley Horse Farm Stay | 10 min to Legoland
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Goshen
Goshen Village Home
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Apr
5.0 out of 5 average rating, 16 reviews