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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, 215 reviews
Guest favourite
Bed and breakfast in Middletown
Charming Upstate New York Inn Cozy Suite #202
4.95 out of 5 average rating, 19 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Bed and breakfast in Middletown
Charming Upstate New York Inn Cozy Suite #203
5.0 out of 5 average rating, 7 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
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
Flat in Middletown
The Columbus Hotel | The District Studio | 89-204
4.8 out of 5 average rating, 5 reviews, 1 bed, 1 bathroom
8–13 Jul
Guest favourite
Home in Montgomery
Modern Woodland Retreat, Hudson Valley & Catskills
4.95 out of 5 average rating, 128 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Goshen
Goshen Village Home
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Chalet in Pine Bush
Spacious A-Frame Getaway near Hiking and Wineries
4.98 out of 5 average rating, 133 reviews, 3 bedrooms, 3 beds, 2 bathrooms
17–22 Jul
Top guest favourite
Flat in Newburgh
Special Nest w Private Entrance River View Porches
4.89 out of 5 average rating, 264 reviews, 1 bedroom, 1 bed, 2 bathrooms
13–18 Sept
Top guest favourite
Cottage in Montgomery
The Pullman Cottage NYC Escape • Dogs Stay Free
5.0 out of 5 average rating, 81 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Jul
Top guest favourite
Farm stay in Middletown
Hudson Valley Horse Farm Stay | 10 min to Legoland
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 2 beds, 1 bathroom
8–13 Jul
Top guest favourite
Flat in Montgomery
A modern oasis in the Hudson Valley and nature.
4.98 out of 5 average rating, 47 reviews, 2 bedrooms, 2 beds, 1 bathroom
21–26 Jul
Guest favourite
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
4.91 out of 5 average rating, 326 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
19–24 Jul
Top guest favourite
Bed and breakfast in Goshen
Parkway House Goshen Bed & Breakfast Suite #2
5.0 out of 5 average rating, 19 reviews, 2 bedrooms, 4 beds, 1 bathroom
10–15 Jul
Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
26–31 Jul
Guest favourite
Cottage in Pine Bush
Modern 3BR BoHo Retreat/Nearby Hiking, Wineries
4.94 out of 5 average rating, 126 reviews, 3 bedrooms, 3 beds, 1 bathroom
15–20 Aug
Guest favourite
Room in Sussex
Secluded setting, queen size bed
4.94 out of 5 average rating, 474 reviews, 1 queen bed, 2 bathrooms
12–17 Jul
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