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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
12–17 Sept
4.96 out of 5 average rating, 28 reviews
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
2 beds
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Flat in Middletown
The Columbus Hotel | The Residence Studio | 89-206
1 double bed
17–22 Aug
Top guest favourite
Home in Middletown
Peace and quiet. Comfy, private house to relax in
4 bedrooms, 4 beds
12–17 Oct
4.98 out of 5 average rating, 218 reviews
Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds
14–19 Aug
5.0 out of 5 average rating, 20 reviews
Guest favourite
Cabin in Ellenville
Catskills Cabin, Hot Tub, Wood Stove, King Bed
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 227 reviews
Top guest favourite
Home in Goshen
Cozy Brookside Cottage on the Farm
1 bedroom, 2 beds
7–12 Sept
4.94 out of 5 average rating, 95 reviews
Luxe
Villa in Middletown
Pinnacle Pointe | Year-Round Pool Spa Lake Theater
7 bedrooms, 12 beds
31 Aug – 5 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Barn in Montgomery
16taft
2 queen beds
16–21 Aug
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Warwick
village oasis
1 bedroom, 2 beds
16–21 Aug
4.98 out of 5 average rating, 82 reviews
Guest favourite
Cottage in Pine Bush
Modern 3BR BoHo Retreat/Nearby Hiking, Wineries
3 bedrooms, 3 queen beds
15–20 Aug
4.93 out of 5 average rating, 133 reviews
Top guest favourite
Cottage in Montgomery
The Pullman Cottage NYC Escape • Dogs Stay Free
2 bedrooms, 2 queen beds
18–23 Dec
5.0 out of 5 average rating, 86 reviews
Top guest favourite
Farm stay in Goshen
Bright Farm House- Tranquil setting
3 bedrooms, 5 beds
26 Sept – 1 Oct
4.89 out of 5 average rating, 414 reviews
Top guest favourite
Home in Wurtsboro
The Alexandria - Wurstboro, NY
3 bedrooms, 5 beds
29 Sept – 4 Oct
4.97 out of 5 average rating, 73 reviews
Guest favourite
Room in Slate Hill
Stone Oak Tree Farm White Spruce Rm
1 queen bed
14–19 Aug
4.98 out of 5 average rating, 41 reviews
Guest favourite
Flat in Newburgh
Special Nest w Private Entrance River View Porches
1 bedroom, 1 queen bed
2–7 Nov
4.89 out of 5 average rating, 270 reviews
Guest favourite
Barn in Middletown
The Elm Barn- long term OK
2 bedrooms, 4 beds
17–22 Aug
4.79 out of 5 average rating, 98 reviews
Top guest favourite
Cottage in Florida
Family Stay: Legoland & Wine Country Living!
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 65 reviews