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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, 216 reviews
Guest favourite
Bed and breakfast in Middletown
Charming Upstate New York Inn Cozy Suite #202
4.96 out of 5 average rating, 25 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Bed and breakfast in Middletown
Charming Upstate New York Inn Cozy Suite #203
5.0 out of 5 average rating, 10 reviews, 1 bedroom, 2 beds, 1 bathroom
24–29 Jul
Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
5.0 out of 5 average rating, 17 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
26–31 Jul
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
Cabin in Grahamsville
1920s Southwestern-styled mountain escape.
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Flat in Middletown
The Columbus Hotel | The Galley Studio | 89-203
New place to stay, 1 bed, 1 bathroom
14–19 Jul
Guest favourite
Flat in Newburgh
Special Nest w Private Entrance River View Porches
4.89 out of 5 average rating, 266 reviews, 1 bedroom, 1 bed, 2 bathrooms
13–18 Sept
Guest favourite
Flat in Pine Bush
Explore and Relax On The Knoll
4.91 out of 5 average rating, 33 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Aug
Top guest favourite
Cabin in Wurtsboro
Forest Spa Retreat on Cascading Brook • 90 Min NYC
4.95 out of 5 average rating, 441 reviews, 3 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Glen Wild
3BR Catskills Getaway Retreat!
4.98 out of 5 average rating, 42 reviews, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
Home in Port Jervis
Little Palace.
New place to stay, 2 bedrooms, 2 beds, 2 bathrooms
29 Jul – 3 Aug
Top guest favourite
Home in Wurtsboro
The Alexandria - Wurstboro, NY
4.97 out of 5 average rating, 69 reviews, 3 bedrooms, 5 beds, 1 bathroom
15–20 Sept
Superhost
Home in Highland
VIEWS on Hudson River / Luxury Modern Home
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
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
20–25 Jul
Top guest favourite
Cabin in Ellenville
Catskills Cabin, Hot Tub, Wood Stove, King Bed
4.99 out of 5 average rating, 219 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Place to stay in Middletown
Charming Bedroom Close to Legoland & Shopping
1 bedroom, 1 bed, 1.5 bathrooms
14–19 Jul
Guest favourite
Cabin in Sussex
Near Mt Creek, Lake Glenwood, Crystal Cabin-Vernon
4.9 out of 5 average rating, 92 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 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
14–19 Jul