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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
4.96 out of 5 average rating, 25 reviews, 1 queen bed, 1 bathroom
2–7 Aug
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
5.0 out of 5 average rating, 10 reviews, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Middletown
Peace and quiet. Comfy, private house to relax in
4.98 out of 5 average rating, 217 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
2–7 Aug
Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
5.0 out of 5 average rating, 17 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
1–6 Aug
Guest favourite
Barn in Middletown
The Elm Barn- long term OK
4.79 out of 5 average rating, 98 reviews, 2 bedrooms, 4 beds, 3 bathrooms
1–6 Aug
Guest favourite
Room in Otisville
B3 Cozy private RM Otisville Middletown Deer park
5.0 out of 5 average rating, 16 reviews, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
Luxe
Villa in Middletown
Pinnacle Pointe | Year-Round Pool Spa Lake Theater
4.88 out of 5 average rating, 8 reviews, 7 bedrooms, 12 beds, 8 bathrooms
31 Aug – 5 Sept
Guest favourite
Home in Warwick
SPACIOUS COUNTRY GETAWAY - JUST 50 MILES FROM GWB!
4.95 out of 5 average rating, 130 reviews, 4 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Chalet in Wurtsboro
Gorgeous Chalet with Lots of Room!
4.96 out of 5 average rating, 244 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Chester
4 Bedroom Home with Hot-Tub
5.0 out of 5 average rating, 48 reviews, 4 bedrooms, 10 beds, 2.5 bathrooms
21–26 Aug
Top guest favourite
Cottage in Pine Bush
Modern 3BR BoHo Retreat/Nearby Hiking, Wineries
4.95 out of 5 average rating, 129 reviews, 3 bedrooms, 3 beds, 1 bathroom
15–20 Aug
Top guest favourite
Flat in Montgomery
Cozy studio apartment with everything you need!
4.95 out of 5 average rating, 20 reviews, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Home in Newburgh
Midcentury Wow! River views, Heated Pool & Hot Tub
4.98 out of 5 average rating, 144 reviews, 5 bedrooms, 6 beds, 3.5 bathrooms
1–6 Aug
Guest favourite
Flat in Montgomery
Montgomery Village King Bed 2BR/2B Ground Floor
4.88 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Cabin in Wurtsboro
Forest Spa Retreat on Cascading Brook • 90 Min NYC
4.95 out of 5 average rating, 441 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Cabin in Grahamsville
1920s Southwestern-styled mountain escape.
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Guest favourite
Home in Montgomery
Luxury 10 Acres Estate: Pool, Fire Pit, Playground
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 9 beds, 2.5 bathrooms
17–22 Aug
Top guest favourite
Home in Goshen
Cozy Brookside Cottage on the Farm
4.94 out of 5 average rating, 95 reviews, 1 bedroom, 2 beds, 1 bathroom
7–12 Sept