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Search results; Over 1,000 homes in Middletown

Top guest favorite
Home in Middletown
Wooded 8 acres with a fire pit
4 bedrooms, 4 beds, 1.5 private baths
Oct 12 – 17
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4.98 out of 5 average rating, 218 reviews
Guest favorite
Room in Middletown
Rustic inn near trails and wineries
4.96 out of 5 average rating, 28 reviews, 1 queen bed, 1 bath
Sep 12 – 17
Apartment in Middletown
Downtown studio with free parking
1 bed, 1 bath
Aug 12 – 17
Guest favorite
Room in Middletown
Rustic inn near hiking and wineries
5.0 out of 5 average rating, 12 reviews, 2 beds, 1 bath
Aug 15 – 20
Top guest favorite
Home in Middletown
Hilltop on 14 acres with 360 views
5.0 out of 5 average rating, 20 reviews, 4 bedrooms, 6 beds, 3.5 baths
Aug 14 – 19
Top guest favorite
Room in Sussex
Peaceful 3-acre lot near Mountain Creek
4.93 out of 5 average rating, 358 reviews, 2 beds, 2 baths
Aug 16 – 21
Top guest favorite
Guesthouse in Wurtsboro
Secluded forest loft above Bashakill Refuge
4.92 out of 5 average rating, 130 reviews, 1 bedroom, 2 beds, 1 bath
Aug 30 – Sep 4
Top guest favorite
Apartment in Montgomery
Renovated studio in a wooded country setting
4.96 out of 5 average rating, 23 reviews, 1 bed, 1 bath
Aug 16 – 21
Top guest favorite
Chalet in Pine Bush
A-frame with a fire pit near wineries
4.98 out of 5 average rating, 138 reviews, 3 bedrooms, 3 beds, 2 baths
Oct 11 – 16
Top guest favorite
Room in Hamptonburgh
Farmhouse on 33 acres with trails
5.0 out of 5 average rating, 8 reviews, 1 king bed, 1 bath
Aug 12 – 17
Top guest favorite
Farm stay in Middletown
Lakefront cottage on a horse farm
5.0 out of 5 average rating, 12 reviews, 1 bedroom, 2 beds, 1 bath
Aug 12 – 17
Top guest favorite
Rooms in Goshen
Victorian inn with track-view wrap-around porch
5.0 out of 5 average rating, 20 reviews, 2 bedrooms, 4 beds, 1 bath
Aug 16 – 21
Top guest favorite
Tiny home in Pine Bush
Creek-view deck with a built-in fire pit
4.99 out of 5 average rating, 86 reviews, 1 bed, 1 bath
Aug 24 – 29
Top guest favorite
Home in Montgomery
Open-concept home with a chef’s kitchen
5.0 out of 5 average rating, 23 reviews, 3 bedrooms, 3 beds, 2.5 baths
Aug 27 – Sep 1
Top guest favorite
Rooms in Goshen
Restored Victorian inn with wrap-around porch
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 12 – 17
Guest favorite
Apartment in Chester
Deck with pond view in Sugar Loaf
4.96 out of 5 average rating, 427 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 30 – Sep 4
Top guest favorite
Cottage in Goshen
Peaceful farm cottage 10 min from LEGOLAND
4.92 out of 5 average rating, 336 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 13 – 18
Top guest favorite
Barn in Montgomery
Vaulted ceilings and a fieldstone fire pit
4.98 out of 5 average rating, 43 reviews, 2 beds, 1 bath
Aug 16 – 21
Top guest favorite
Home in Rock Hill
Lakefront Catskills retreat with a canoe
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 14 – 19