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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
Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds, 3.5 bathrooms
15–20 Aug
5.0 out of 5 average rating, 21 reviews
Flat in Middletown
The Columbus Hotel | The Residence Studio | 89-206
1 double bed, 1 bathroom
17–22 Aug
Guest favourite
Flat in Montgomery
Montgomery Village King Bed 2BR/2B Ground Floor
2 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Barn in Montgomery
16taft
2 queen beds, 1 bathroom
16–21 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
15–20 Aug
4.93 out of 5 average rating, 133 reviews
Top guest favourite
Flat in Warwick
village oasis
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 82 reviews
Guest favourite
Cabin in Ellenville
Catskills Cabin, Hot Tub, Wood Stove, King Bed
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 227 reviews
Guest favourite
Flat in Newburgh
Special Nest w Private Entrance River View Porches
1 bedroom, 1 queen bed, 2 bathrooms
2–7 Nov
4.89 out of 5 average rating, 270 reviews
Guest favourite
Room in Slate Hill
Stone Oak Tree Farm White Spruce Rm
1 queen bed, 1 bathroom
15–20 Aug
4.98 out of 5 average rating, 41 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
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
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
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
Guest favourite
Cabin in Sparrow Bush
Lakeside Retreat w/Fire Pit & Skylights
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 226 reviews
Guest favourite
Guest suite in Montgomery
the Guest Suite at Dunhill Pond
1 bedroom, 1 king bed, 1 bathroom
15–20 Aug
4.88 out of 5 average rating, 57 reviews