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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
19–24 Jul
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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 Port Jervis
Little Palace.
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Cabin in Grahamsville
1920s Southwestern-styled mountain escape.
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
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
29 Sept – 4 Oct
Top guest favourite
Guest suite in Goshen
Private Guest Suite at Hudson Valley Happy Place!
4.98 out of 5 average rating, 320 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Jul – 4 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
Top 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
27 Jul – 1 Aug
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
Home in Glen Wild
3BR Catskills Getaway Retreat!
4.98 out of 5 average rating, 43 reviews, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
Guest favourite
Cabin in Ellenville
Catskills Cabin, Hot Tub, Wood Stove, King Bed
4.99 out of 5 average rating, 220 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
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
Apartment in Vernon Township
Cozy Luxury Mountain Retreat 2BR/2BA | Water Park
4.98 out of 5 average rating, 112 reviews, 2 bedrooms, 4 beds, 2 bathrooms
12–17 Aug
Guest favourite
Room in Pine Bush
Tranquil Acres South Suite
4.96 out of 5 average rating, 168 reviews, 2 beds, 1 bathroom
9–14 Sept
Top guest favourite
Home in Slate Hill
The Wooden Igloo Near Legoland NY
5.0 out of 5 average rating, 20 reviews, 6 bedrooms, 7 beds, 3.5 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
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
4.91 out of 5 average rating, 329 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept