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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
12–17 Oct
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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
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, 1 bathroom
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, 1 bathroom
17–22 Aug
Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds, 3.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Goshen
Cozy Brookside Cottage on the Farm
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 95 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
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
Home in Wurtsboro
The Alexandria - Wurstboro, NY
3 bedrooms, 5 beds, 1 bathroom
20–25 Oct
4.97 out of 5 average rating, 73 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, 414 reviews
Guest favourite
Cabin in Ellenville
Catskills Cabin, Hot Tub, Wood Stove, King Bed
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.98 out of 5 average rating, 227 reviews
Top guest favourite
Cottage in Florida
Family Stay: Legoland & Wine Country Living!
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 65 reviews
Home in Otisville
3BedRM Cozy Home Otisville Middletown Deer Park
3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.8 out of 5 average rating, 5 reviews
Top guest favourite
Apartment in Vernon Township
Skiiis N’ Tees • Mountain Views • Pet Friendly
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 149 reviews
Guest favourite
Barn in Middletown
The Elm Barn- long term OK
2 bedrooms, 4 beds, 3 bathrooms
17–22 Aug
4.79 out of 5 average rating, 98 reviews
Top guest favourite
Home in Warwick
Deer Pond Lodge Lawn Games Hot Tub Game Room 1Pet
4 bedrooms, 5 beds, 3 bathrooms
24–29 Aug
4.95 out of 5 average rating, 44 reviews
Top guest favourite
Cottage in Montgomery
The Pullman Cottage NYC Escape • Dogs Stay Free
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Dec
5.0 out of 5 average rating, 86 reviews
Guest favourite
Chalet in Wurtsboro
Gorgeous Chalet with Lots of Room!
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 246 reviews