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Search results; Over 1,000 homes in Middletown

Home in Middletown
Secluded Farmhouse, 30 acres private estate.
6 bedrooms, 8 beds, 2.5 private bathrooms
30 Aug – 4 Sept
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4.7 out of 5 average rating, 117 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
Peace and quiet. Comfy, private house to relax in
4.98 out of 5 average rating, 217 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
2–7 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
10–15 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, 9 reviews, 2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
Guest favourite
Guest suite in Chester
Serene Victorian Guest Apartment with Clawfoot Tub
4.94 out of 5 average rating, 391 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Home in Port Jervis
Little Palace.
4.83 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
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
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
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
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
Chalet in Wurtsboro
Gorgeous Chalet with Lots of Room!
4.96 out of 5 average rating, 246 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 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
Cabin in Wurtsboro
Forest Spa Retreat on Cascading Brook • 90 Min NYC
4.95 out of 5 average rating, 443 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Home in Otisville
3BedRM Cozy Home Otisville Middletown Deer Park
4.75 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 1 bathroom
17–22 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 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