Vacation Rentals in Middletown, NY

This Relaxtay mountain estate is located in Bloomingburg, approximately 161 kilometres from New York City, set on 971,245 square metres of private land with panoramic mountain views.
This expansive 9,500 sq ft lodge offers accommodation for 16 guests, featuring a year-round heated pool, a private lake with kayaks and a boat, a home cinema, arcade, pool table, bar, full gym, and spa facilities including a sauna and massage chairs, alongside a chef’s kitchen, outdoor dining areas, a firepit, mini golf, and a playground.

This spacious apartment is located in a picturesque setting in Chester, just a short distance from the city centre and its historic attractions. It has received excellent ratings for its cleanliness, location, and user experience.
The apartment spans three floors and can accommodate up to 16 guests, providing ample space for large families or groups. It boasts a fully equipped kitchen, a swimming pool, a tennis court, and dedicated children's areas, making it perfect for a memorable family holiday.

This log cabin-style house is located in a quiet, private setting just minutes from Middletown, offering easy access to major shopping areas and restaurants. The property has received excellent ratings for location, cleanliness, and user experience.
The cabin offers three bedrooms and one bathroom, accommodating up to twelve guests. Guests can enjoy amenities such as a sauna, swimming pool, and a private garden, along with a range of entertainment options including a flat-screen TV, video games, and a fire pit.

This Goshen, New York holiday home is situated approximately 5 kilometres from Goshen Historic Track and the Orange County Genealogical Society, and within 10 kilometres of LEGOLAND® New York and the Harness Racing Museum & Hall of Fame.
This smoke-free, family-friendly property sleeps ten guests in four bedrooms and two bathrooms, offering a fully equipped kitchen, air conditioning, parking, Wi-Fi, and barbecue facilities.

This lakeside lodge is situated near Otisville, New York, within 5 kilometres of Gobbler's Knob State Forest, Otisville Veterans Memorial Park, and Delaware and Hudson Canal County Park.
Sleeping six guests, this four-bedroom, three-bathroom property boasts a fully equipped kitchen, a fireplace, terrace, and garden; enjoy nearby water activities and the convenience of internet access.

This glamping tent is situated just a short drive from Middletown, offering easy access to local attractions and amenities. It's located in a peaceful setting, ideal for a relaxing getaway. The tent boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The accommodation sleeps up to 12 guests and features a private outdoor area with seating, hammocks, a grill, and a picnic table. Guests can also enjoy discounted access to nearby attractions like a ropes course, paintball, and a "Camo Run Tube Ride", as well as shared pool access and convenient amenities like portable bathrooms and showers.

This Hudson Valley lakefront cottage near Middletown, approximately 11 kilometres from Goshen Village and 1 hour 15 minutes from New York City, offers a unique farmstay experience on a 7-acre horse farm with easy access to LEGOLAND New York, Brotherhood Winery, and Goshen Historic Track.
The one-bedroom, one-bathroom property sleeps two, features a full kitchen with microwave and dishwasher, air conditioning, private parking, a private dock with canoe and paddleboat, and a fenced courtyard; amenities include beach towels, toiletries, and a pack 'n play (toddler bed available on request).

This Middletown, New York apartment rental is centrally located, minutes from Touro College and Garnet Health Medical Center, and approximately 80 kilometres from New York City.
The fully furnished suite offers a private kitchen, bathroom, and high-speed Wi-Fi, accommodating two guests with a shared laundry and secure parking; mid-stay cleaning is included.

This studio flat is located in Middletown's downtown district, 200 meters from the Middletown Arts Centre and Old Town Square.
This 21 square meter studio offers air conditioning, a kitchen with a fridge and microwave, and a balcony, accommodating up to three guests with a 10:00 AM check-out.

This luxury private estate, offering 965 hectares of seclusion, is located 37 kilometres from Stewart International Airport and 37 kilometres from DM Weil Gallery in High View.
This 7-bedroom villa boasts 863 square meters of floor area, accommodates up to 47 guests, and features a swimming pool, jacuzzi, sauna, fitness centre, billiards, and table tennis, with golf, fishing, canoeing, and hiking available nearby.

This Serene Rustic Retreat near Otisville, New York, offers a peaceful escape approximately 45km from the DM Weil Gallery and 47km from Stewart International Airport.
The 149 square metre property boasts three bedrooms, three bathrooms, and can comfortably accommodate up to eleven guests, featuring a fully equipped kitchen, Jacuzzi, private parking, and complimentary Wi-Fi.

This Goshen villa, 22.5km from Bear Mountain State Park and 22.5km from Harriman Metro-North Station, offers easy access to both outdoor pursuits and New York City.
Sleeping up to 25 guests, this three-bathroom property boasts an Alaska King-size bed, private pool and jacuzzi, fully equipped kitchen, terrace, balcony, free Wi-Fi, and private parking.

This glamping shelter is situated just a short drive from Middletown, offering easy access to shopping, dining, and attractions like Legoland and local wineries. The site has received excellent ratings for its location, cleanliness, and overall experience.
The accommodation can sleep up to nine guests and comes with a double bed and additional bedding, as well as a private bathroom. Guests can enjoy a range of amenities including a swimming pool, a Jacuzzi, a fire pit, a picnic table, and a hammock, as well as solar electricity.

This glamping shelter is located just a short drive from Middletown, offering easy access to shopping, restaurants, and attractions like Legoland and local wineries. The property enjoys excellent ratings for user experience, location, and cleanliness.
The tent sleeps up to 9 guests and comes with basic linen, a fire pit, a grill, and a picnic table. You can also enjoy the on-site swimming pool, jacuzzi, and a range of additional activities and amenities.

This glamping shelter is located just a few kilometres from Middletown, providing easy access to shopping, restaurants, and attractions like Legoland and local wineries. The surrounding area is quiet and peaceful, offering a tranquil escape from the hustle and bustle of everyday life.
The White Owl-soar With The Birds offers a comfortable stay for up to nine guests. The tent is equipped with a bed, linens, a picnic table, a hammock, a grill, a fire pit, a swimming pool, and solar electricity.

This spacious house is located in a peaceful rural setting near Goshen, just a short drive from popular attractions like LEGOLAND® New York and Castle Fun Center, making it a great base for exploring the area. The house has received excellent reviews from previous guests, highlighting its comfortable and convenient amenities.
The property has five bedrooms and three bathrooms, comfortably accommodating up to ten guests. Enjoy a dip in the private pool, relax in the hot tub, or cook up a meal on the barbecue, all while taking in the tranquil surroundings.