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Search results; Over 1,000 homes in Middletown

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Home in Middletown
Secluded Farmhouse, 30 acres private estate.
6 bedrooms, 8 beds, 2.5 private bathrooms
5–10 Oct
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4.7 out of 5 average rating, 117 reviews
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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, 38 reviews
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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
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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
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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
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Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds, 3.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Room in Hamptonburgh
Hudson Haven, Master Suite
1 king bed, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Cottage in Montgomery
The Pullman Cottage • Hudson Valley
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Dec
5.0 out of 5 average rating, 90 reviews
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Guest favourite
Camper van/Motorhome in Montgomery
The Coop
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Home in Wurtsboro
Bashakill Hillside Cottage East
2 bedrooms, 2 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Home in Sparrow Bush
Cozy River Valley Retreat w/ Fireplace & Deck
4 bedrooms, 5 beds, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 33 reviews
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Guest favourite
Room in Slate Hill
Stone Oak Tree Farm Canaan Fir Room
1 queen bed, 1 bathroom
18–23 Sept
4.98 out of 5 average rating, 112 reviews
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Top guest favourite
Home in Wurtsboro
The Alexandria - Wurstboro, NY
3 bedrooms, 5 beds, 1 bathroom
2–7 Nov
4.97 out of 5 average rating, 77 reviews
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Top guest favourite
Home in Goshen
Cozy Brookside Cottage on the Farm
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 96 reviews
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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
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Top guest favourite
Flat in Warwick
village oasis
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
4.98 out of 5 average rating, 88 reviews
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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
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Top guest favourite
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
2 bedrooms, 2 beds, 1 bathroom
11–16 Nov
4.92 out of 5 average rating, 349 reviews
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Top guest favourite
Home in Middletown
5Bdrm Estate/Tennis near LegoLand
5 bedrooms, 7 beds, 2.5 bathrooms
19–24 Sept
4.97 out of 5 average rating, 72 reviews