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Search results; Over 1,000 homes in Middletown

Top guest favourite
Home in Middletown
Peace and quiet. Comfy, private house to relax in
4 bedrooms, 4 beds, 1.5 private bathrooms
2–7 Aug
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4.98 out of 5 average rating, 217 reviews
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #202
4.96 out of 5 average rating, 25 reviews, 1 queen bed, 1 bathroom
2–7 Aug
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
5.0 out of 5 average rating, 10 reviews, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
5.0 out of 5 average rating, 18 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
1–6 Aug
Guest favourite
Barn in Middletown
The Elm Barn- long term OK
4.79 out of 5 average rating, 98 reviews, 2 bedrooms, 4 beds, 3 bathrooms
1–6 Aug
Luxe
Villa in Middletown
Pinnacle Pointe | Year-Round Pool Spa Lake Theater
4.88 out of 5 average rating, 8 reviews, 7 bedrooms, 12 beds, 8 bathrooms
31 Aug – 5 Sept
Top guest favourite
Home in Goshen
Goshen Village Home
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Chalet in Wurtsboro
Gorgeous Chalet with Lots of Room!
4.96 out of 5 average rating, 244 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Cottage in Pine Bush
Modern 3BR BoHo Retreat/Nearby Hiking, Wineries
4.95 out of 5 average rating, 129 reviews, 3 bedrooms, 3 beds, 1 bathroom
15–20 Aug
Top guest favourite
Home in Goshen
Cozy Brookside Cottage on the Farm
4.94 out of 5 average rating, 95 reviews, 1 bedroom, 2 beds, 1 bathroom
7–12 Sept
Top guest favourite
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
4.92 out of 5 average rating, 330 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Flat in Montgomery
Cozy studio apartment with everything you need!
4.95 out of 5 average rating, 20 reviews, 1 bed, 1 bathroom
16–21 Aug
Guest favourite
Home in Warwick
SPACIOUS COUNTRY GETAWAY - JUST 50 MILES FROM GWB!
4.95 out of 5 average rating, 130 reviews, 4 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Farm stay in Middletown
Hudson Valley Horse Farm Stay | 10 min to Legoland
5.0 out of 5 average rating, 10 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Guest house in Wurtsboro
Hiker’s Haven, a Cozy Cabin above Bashakill Refuge
4.91 out of 5 average rating, 122 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Chester
4 Bedroom Home with Hot-Tub
5.0 out of 5 average rating, 49 reviews, 4 bedrooms, 10 beds, 2.5 bathrooms
21–26 Aug
Guest favourite
Flat in Montgomery
Montgomery Village King Bed 2BR/2B Ground Floor
4.88 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Guest favourite
Cabin in Ellenville
Catskills Cabin, Hot Tub, Wood Stove, King Bed
4.99 out of 5 average rating, 221 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Room in Otisville
B1 Cozy private RM Otisville Middletown Deer park
5.0 out of 5 average rating, 21 reviews, 1 queen bed, 1 bathroom
28 Sept – 3 Oct