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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
9–14 Nov
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4.98 out of 5 average rating, 224 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
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
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
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
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
5Bdrm Estate/Tennis near LegoLand
5 bedrooms, 7 beds, 2.5 bathrooms
15–20 Sept
4.97 out of 5 average rating, 71 reviews
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, 348 reviews
Top guest favourite
Home in Middletown
Private Secret Escape • Hot Tub • Pool • Fire Pit
4 bedrooms, 8 beds, 2.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Goshen
Goshen Village Home
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Apr
5.0 out of 5 average rating, 16 reviews
Guest favourite
Cabin in Cuddebackville
Riverfront Retreat | Hot Tub, Firepit & Pool Table
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 128 reviews
Top guest favourite
Flat in Goshen
Carriage House Apartment Close to Legoland NY
3 bedrooms, 4 beds, 1.5 bathrooms
17–22 Oct
4.96 out of 5 average rating, 126 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
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.96 out of 5 average rating, 435 reviews
Guest favourite
Villa in Bloomingburg
Spacious 6BR Villa | Serene Scenic Mountain Escape
6 bedrooms, 11 beds, 3 bathrooms
20–25 Sept
4.87 out of 5 average rating, 117 reviews
Top guest favourite
Home in Glen Wild
3BR Catskills Getaway Retreat!
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Cottage in Florida
Fall Fun, Apple Picking, Wineries & LegoLand!
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 69 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