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Search results; Over 1,000 homes in Middletown

Superhost
Tent in Middletown
Victor-amazing glamping experience-Middletown NY
1 bedroom, 4 beds, 1.5 bathrooms
14–19 Sept
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4.67 out of 5 average rating, 21 reviews
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #202
1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 37 reviews
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
2 beds, 1 bathroom
27 Sept – 2 Oct
4.94 out of 5 average rating, 17 reviews
Superhost
Home in Woodridge
Hotel Buyout | 54 Guests | Belvedere Suites
18 bedrooms, 45 beds, 18 bathrooms
18–23 Sept
5.0 out of 5 average rating, 3 reviews
Luxe
Villa in Middletown
Pinnacle Pointe | Year-Round Pool Spa Lake Theater
7 bedrooms, 12 beds, 8 bathrooms
18–23 Sept
4.92 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 Sept
5.0 out of 5 average rating, 21 reviews
Guest favourite
Flat in Newburgh
Special Nest w Private Entrance River View Porches
1 bedroom, 1 queen bed, 2 bathrooms
27 Nov – 2 Dec
4.89 out of 5 average rating, 279 reviews
Top guest favourite
Barn in Montgomery
16taft
2 queen beds, 1 bathroom
19–24 Sept
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Farm stay in Middletown
Hudson Valley Horse Farm Stay | 10 min to Legoland
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 14 reviews
Home in Montgomery
Walk to Village! 5BR Home, 2 Kitchens, King Beds
6 bedrooms, 8 beds, 4.5 bathrooms
22–27 Oct
Home in Montgomery
Cozy Montgomery Home
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Dec
New place to stay
Guest favourite
Room in Montgomery
Timless Elegance: Hummingbird Queen Suite
1 queen bed, 1 bathroom
20–25 Sept
4.81 out of 5 average rating, 79 reviews
Guest favourite
Guest suite in Montgomery
the Guest Suite at Dunhill Pond
1 bedroom, 1 king bed, 1 bathroom
18–23 Sept
4.88 out of 5 average rating, 57 reviews
Top guest favourite
Home in Middletown
Peace and quiet. Comfy, private house to relax in
4 bedrooms, 4 beds, 1.5 bathrooms
9–14 Nov
4.98 out of 5 average rating, 224 reviews
Guest favourite
Home in Montgomery
The Ferns at Winding Hills
4 bedrooms, 5 beds, 4 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 11 reviews
Home in Otisville
3BedRM Cozy Home Otisville Middletown Deer Park
3 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.71 out of 5 average rating, 7 reviews
Top guest favourite
Villa in Goshen
Goshen Retreat w/ Hot Tub & Pool near Legoland
5 bedrooms, 7 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 25 reviews
Guest favourite
Cottage in Pine Bush
Modern 3BR BoHo Retreat/Nearby Hiking, Wineries
3 bedrooms, 3 queen beds, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 133 reviews
Guest favourite
Flat in Pine Bush
Explore and Relax On The Knoll
1 bedroom, 2 beds, 1 bathroom
19–24 Nov
4.91 out of 5 average rating, 35 reviews