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Search results; Over 1,000 homes in Middletown

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Superhost
Tent in Middletown
9 person- Glamping Tent Site- Aphrodite
1 bedroom, 8 beds, 1 shared bathroom
1–6 Sept
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5.0 out of 5 average rating, 4 reviews
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Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #202
1 queen bed
13–18 Sept
4.97 out of 5 average rating, 33 reviews
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Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
2 beds
7–12 Sept
4.92 out of 5 average rating, 13 reviews
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Superhost
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds
1–6 Sept
5.0 out of 5 average rating, 21 reviews
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Guest favourite
Flat in Pine Bush
Explore and Relax On The Knoll
1 bedroom, 2 beds
13–18 Oct
4.91 out of 5 average rating, 35 reviews
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Top guest favourite
Chalet in Pine Bush
Spacious A-Frame Getaway near Hiking and Wineries
3 bedrooms, 3 beds
27 Nov – 2 Dec
4.98 out of 5 average rating, 140 reviews
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Luxe
Villa in Middletown
Pinnacle Pointe | Year-Round Pool Spa Lake Theater
7 bedrooms, 12 beds
1–6 Sept
4.91 out of 5 average rating, 11 reviews
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Top guest favourite
Barn in Montgomery
16taft
2 queen beds
1–6 Sept
4.98 out of 5 average rating, 43 reviews
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Flat in Montgomery
Hudson Valley Modern Apartment. King Bed/Queen
1 bedroom, 3 beds
20–25 Sept
4.97 out of 5 average rating, 75 reviews
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Top guest favourite
Farm stay in Middletown
Hudson Valley Horse Farm Stay | 10 min to Legoland
1 bedroom, 2 beds
1–6 Sept
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Home in Goshen
Goshen Village Home
2 bedrooms, 2 queen beds
1–6 Apr
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Middletown
Peace and quiet. Comfy, private house to relax in
4 bedrooms, 4 beds
12–17 Oct
4.98 out of 5 average rating, 218 reviews
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Home in Montgomery
Walk to Village! 5BR Home, 2 Kitchens, King Beds
6 bedrooms, 8 beds
13–18 Sept
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Top guest favourite
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
2 bedrooms, 2 beds
13–18 Sept
4.92 out of 5 average rating, 341 reviews
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Superhost
Flat in Goshen
Historic Horse Barn Sleeps - 4 Minutes to Legoland
2 bedrooms, 3 beds
13–18 Sept
4.98 out of 5 average rating, 254 reviews
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Guest favourite
Cottage in Pine Bush
Modern 3BR BoHo Retreat/Nearby Hiking, Wineries
3 bedrooms, 3 queen beds
4–9 Oct
4.93 out of 5 average rating, 133 reviews
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Top guest favourite
Flat in Goshen
Carriage House Apartment Close to Legoland NY
3 bedrooms, 4 beds
13–18 Sept
4.96 out of 5 average rating, 123 reviews
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Top guest favourite
Flat in Montgomery
A modern oasis in the Hudson Valley and nature.
2 bedrooms, 2 beds
10–15 Sept
4.98 out of 5 average rating, 52 reviews
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Guest favourite
Cabin in Warwick
Luxury Woodland Cabin w/ Pool near Warwick
3 bedrooms, 3 beds
13–18 Sept
4.86 out of 5 average rating, 63 reviews