Compare Vacation Rentals & Airbnb in Middletown, NY

This rustic glamping shelter is located just a short drive from Middletown, providing easy access to shopping, dining, and attractions like Legoland and local wineries. The surrounding area is peaceful and secluded, perfect for a relaxing getaway.
The Dream offers a unique glamping experience with a focus on a relaxed, nature-inspired setting. It can accommodate up to seven guests and features a comfortable living space with a bedroom and bathroom. Guests can enjoy modern amenities like solar-powered electricity, a grill, fire pit, picnic table, and hammock, as well as on-site activities and amenities available for purchase.

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 newly renovated studio flat is located in the centre of Middletown, NY, offering direct access to Routes 17 and 84, with numerous eateries within 500 metres.
This private accommodation for two guests includes a fridge, freezer, microwave, air conditioning, and parking, making it a convenient base for exploring Orange County attractions.

This glamping shelter is situated just minutes from Middletown, offering easy access to shopping, dining, and attractions like Legoland and local wineries. The surrounding area is quiet and private, perfect for a relaxing getaway.
The Fionna - Amazing Glamping tent can accommodate up to nine guests and features a bedroom and bathroom. Guests can enjoy a range of amenities, including a private outdoor area with a grill, fire pit, and hammock, as well as access to a shared pool and discounted rates at a nearby paintball shop.

This private suite is located in the revitalised Columbus Hotel in downtown Middletown, offering convenient access to dining, Touro College of Osteopathic Medicine, Garnet Health Medical Center, and the Paramount Theatre, all within 1 kilometre of the accommodation.
This well-managed apartment for two guests features a kitchen with a convection cooktop and full-size refrigerator, air conditioning, a garden, and shared laundry facilities, with free parking available across the street.

This studio flat is centrally located in Middletown's downtown district, offering immediate access to dining, cafes, and breweries, and is conveniently situated 700 meters from Touro College and Garnet Health Medical Center.
This accommodation offers a fully equipped kitchen with a fridge, freezer, and microwave, air conditioning, a garden, parking, one bathroom, and capacity for two guests, with self-check-in via a smart lock and access to a shared 24/7 laundry facility.

The Aphrodite Goddess Of Love glamping shelter is situated just a short drive from Middletown, offering easy access to Legoland and local wineries. This accommodation has received excellent ratings for location, cleanliness, and overall user experience.
This one-bedroom, one-bathroom glamping shelter can comfortably accommodate up to nine guests. Enjoy a unique glamping experience with amenities like solar electricity, a grill, a fire pit, a picnic table, a hammock, and a private pool.

This centrally located flat offers a stylish and modern base in Middletown's prime district, providing convenient access to key landmarks and attractions such as the Middletown Museum (500m) and the historic Middletown Abbey (1.2km).
This one-bedroom apartment accommodates two guests and features air conditioning, a kitchen with a fridge, freezer, and microwave, and a garden, making it ideal for travellers seeking a comfortable stay with easy access to local amenities.

This one-bedroom apartment, situated in New Hampton, approximately 32 kilometres from Middletown, offers easy access to Legoland New York and other Hudson Valley attractions.
The 770-square-metre property boasts a spacious layout with a separate living room, fully equipped kitchen, terrace, parking, and sleeps up to nine guests, featuring free Wi-Fi.

This 1917 farmhouse, renovated by superhosts Susan and Charlie, is located in the Hudson Valley, a short drive from Scotchtown, and within 20 minutes of Woodbury Commons, LegoLand, and Angry Orch. The property has received excellent ratings for location, cleanliness, and overall experience.
The farmhouse offers five bedrooms and two bathrooms, comfortably accommodating up to 12 guests. Enjoy a tranquil setting with multiple living areas, a heated pool, a tennis court, a fire pit, and various patios, along with complimentary amenities, on-site yoga and massage services, and easy access to local attractions.

Close to Trails Studio, a self-contained apartment near Wurtsboro, New York, is situated approximately 50 kilometres from Bethel Woods Center for the Arts and 47 kilometres from Stewart International Airport.
This 22-square-metre studio in Otisville, New York, sleeps three guests and boasts a fully equipped kitchen, private balcony, on-site spa, and free Wi-Fi; nearby hiking trails offer scenic exploration.

Parkway House Goshen Bed And Breakfast Suite 1 is situated in Goshen, 22.5 kilometres from Stewart International Airport, 24 kilometres from Metro-North Harriman Station, and 37 kilometres from Bear Mountain State Park.
This recently renovated holiday home offers 900 square metres of living space with 2 bedrooms, 1 bathroom, air conditioning, complimentary WiFi, free private parking, a patio, and an outdoor fireplace, accommodating up to 9 guests.