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Search results; Over 1,000 homes in Middletown

Guest favourite
Tent in Middletown
9 person glamping tent- dreamweaver
1 bedroom, 8 beds, 1 shared bathroom
7–12 Sept
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5.0 out of 5 average rating, 10 reviews
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #202
1 queen bed, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 34 reviews
Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
2 beds, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 15 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
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, 220 reviews
Home in Middletown
Private Secret Escape • Hot Tub • Pool • Fire Pit
4 bedrooms, 8 beds, 2.5 bathrooms
7–13 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
3–8 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
7–12 Sept
4.97 out of 5 average rating, 71 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, 50 reviews
Guest favourite
Villa in Goshen
Goshen Retreat w/ Hot Tub & Pool near Legoland
5 bedrooms, 7 beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 346 reviews
Top guest favourite
Chalet in Warwick
Mountain View Retreat w/ Hot Tub, Theater, and Gym
4 bedrooms, 5 beds, 3.5 bathrooms
7–12 Sept
4.99 out of 5 average rating, 186 reviews
Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 433 reviews
Top guest favourite
Cottage in Florida
Family Stay: Legoland & Wine Country Living!
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 68 reviews
Top guest favourite
Farm stay in Wurtsboro
Hudson Valley Estate |Game Room| Heated Pool| Gym
6 bedrooms, 14 beds, 5.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 30 reviews
Home in Cuddebackville
Relaxing Country Retreat Near Hiking and Resorts
2 bedrooms, 1 queen bed, 1 bathroom
8–13 Sept
Home in Otisville
3BedRM Cozy Home Otisville Middletown Deer Park
3 bedrooms, 3 beds, 1 bathroom
12–17 Sept
4.71 out of 5 average rating, 7 reviews
Top guest favourite
Home in Pine Bush
Jacuzzi · Arcade-Bar · Cinema · Sleeps18 · Pool
7 bedrooms, 9 beds, 5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Apartment in Vernon Township
Luxurious Cozy Mountain Retreat 2BR-2BA - Ski/Spa.
2 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 122 reviews