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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
12–17 Aug
Guest favourite
Room in Sussex
Secluded setting, queen size bed
1 queen bed, 2 bathrooms
14–19 Aug
4.94 out of 5 average rating, 484 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
Campsite in Accord
Canyon Edge off - grid Bungalow
1 queen bed, No bathroom
16–21 Aug
4.95 out of 5 average rating, 548 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
Top guest favourite
Tiny home in Pine Bush
Creekside Cottage
1 bed, 1 bathroom
24–29 Aug
4.99 out of 5 average rating, 86 reviews
Guest favourite
Home in Kerhonkson
Art Studio in the Gunks | Sauna + Forest Views
1 bedroom, 1 queen bed, 1 bathroom
9–14 Sept
4.91 out of 5 average rating, 1098 reviews
Top guest favourite
Room in Hyde Park
Scandinavian Designed Norge Room - 1 of 3 rooms
1 queen bed, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 498 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
Guest favourite
Camper van/Motorhome in New Paltz
Penelope, 1969 Airstream
1 bedroom, 2 king beds, WC
30 Aug – 4 Sept
4.96 out of 5 average rating, 147 reviews
Top guest favourite
Rooms in Goshen
Parkway House Goshen Bed & Breakfast Suite #1
2 bedrooms, 3 beds, 1 bathroom
14–19 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Farm stay in High Falls
Dave's Milk Barn
2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
4.88 out of 5 average rating, 1082 reviews
Home in Chester
Private Estate | Pool, Hot Tub & 10BR Retreat
10 bedrooms, 20 beds, 4.5 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Room in Poughkeepsie
Hudson Pond · Hideaway King Suite · GF Breakfast
1 king bed, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 244 reviews
Guest favourite
Camper van/Motorhome in Montgomery
The Coop
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Place to stay in Accord
Native Soul Stays, a wooded sauna retreat
1 bedroom, 1 king bed, No bathroom
16–21 Aug
4.96 out of 5 average rating, 305 reviews