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Search results; Over 1,000 homes in Middletown

Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #202
1 queen bed, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 30 reviews
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
2 beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds, 3.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 21 reviews
Flat in Middletown
The Columbus Hotel | The Gold Suite | 89-207
1 double bed, 1 bathroom
23–28 Aug
Top guest favourite
Home in Middletown
Peace and quiet. Comfy, private house to relax in
4 bedrooms, 4 beds, 1.5 bathrooms
12–17 Oct
4.98 out of 5 average rating, 218 reviews
Home in Middletown
Secret Escape Hot tub • Pool • Private Location
4 bedrooms, 8 beds, 2.5 bathrooms
30 Aug – 4 Sept
New place to stay
Guest favourite
Home in Wurtsboro
Bashakill Hillside Cottage East
2 bedrooms, 2 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 20 reviews
Luxe
Villa in Middletown
Pinnacle Pointe | Year-Round Pool Spa Lake Theater
7 bedrooms, 12 beds, 8 bathrooms
31 Aug – 5 Sept
4.9 out of 5 average rating, 10 reviews
Home in Otisville
3BedRM Cozy Home Otisville Middletown Deer Park
3 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.67 out of 5 average rating, 6 reviews
Top guest favourite
Barn in Montgomery
16taft
2 queen beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 43 reviews
Guest favourite
Cottage in Pine Bush
Modern 3BR BoHo Retreat/Nearby Hiking, Wineries
3 bedrooms, 3 queen beds, 1 bathroom
30 Aug – 4 Sept
4.93 out of 5 average rating, 133 reviews
Top guest favourite
Farm stay in Goshen
Bright Farm House- Tranquil setting
3 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
4.89 out of 5 average rating, 415 reviews
Top guest favourite
Home in Wurtsboro
The Alexandria - Wurstboro, NY
3 bedrooms, 5 beds, 1 bathroom
2–7 Nov
4.97 out of 5 average rating, 74 reviews
Top guest favourite
Home in Glen Wild
3BR Catskills Getaway Retreat!
3 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
4.98 out of 5 average rating, 49 reviews
Top guest favourite
Room in Hamptonburgh
Hudson Haven, Master Suite
1 king bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Room in Slate Hill
Stone Oak Tree Farm White Spruce Rm
1 queen bed, 1 bathroom
21–26 Aug
4.98 out of 5 average rating, 41 reviews
Guest favourite
Barn in Middletown
The Elm Barn- long term OK
2 bedrooms, 4 beds, 3 bathrooms
22–27 Aug
4.79 out of 5 average rating, 98 reviews
Top guest favourite
Cabin in Wurtsboro
Escape to a Streamside Cabin in the Catskills
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 114 reviews