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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
7–12 Sept
,
4.98 out of 5 average rating, 218 reviews
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #202
1 queen bed, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 28 reviews
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds, 3.5 bathrooms
14–19 Aug
5.0 out of 5 average rating, 19 reviews
Guest favourite
Cabin in Ellenville
Catskills Cabin, Hot Tub, Wood Stove, King Bed
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 225 reviews
Top guest favourite
Cottage in Montgomery
The Pullman Cottage NYC Escape • Dogs Stay Free
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 85 reviews
Top guest favourite
Barn in Montgomery
16taft
2 queen beds, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 42 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
Top guest favourite
Flat in Montgomery
Cozy studio apartment with everything you need!
1 queen bed, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Home in Glen Wild
3BR Catskills Getaway Retreat!
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.98 out of 5 average rating, 45 reviews
Top guest favourite
Tiny home in Pine Bush
Creekside Cottage
1 bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 86 reviews
Guest favourite
Room in Slate Hill
Stone Oak Tree Farm White Spruce Rm
1 queen bed, 1 bathroom
6–11 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Goshen
Carriage House Apartment Close to Legoland NY
3 bedrooms, 4 beds, 1.5 bathrooms
6–11 Aug
4.97 out of 5 average rating, 121 reviews
Top guest favourite
Guest house in Wurtsboro
Hiker’s Haven, a Cozy Cabin above Bashakill Refuge
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 129 reviews
Flat in Middletown
The Columbus Hotel | The Residence Studio | 89-206
1 double bed, 1 bathroom
6–11 Aug
New place to stay
Home in Otisville
3BedRM Cozy Home Otisville Middletown Deer Park
3 bedrooms, 3 beds, 1 bathroom
19–24 Aug
4.8 out of 5 average rating, 5 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
4.95 out of 5 average rating, 131 reviews
Guest favourite
Flat in Pine Bush
Explore and Relax On The Knoll
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
4.91 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Warwick
village oasis
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 79 reviews