Holiday Rentals in Middletown, NY

This spacious New Farmhouse, sleeping up to 22 guests, is situated approximately 24 kilometres from the DM Weil Gallery in Montgomery, 34 kilometres from Loren Campbell Baseball Field and SUNY New Paltz, and 15 kilometres from Stewart International Airport.
The 465-square-metre property boasts six bedrooms, five bathrooms, two living rooms, a fully equipped kitchen, a jacuzzi, a fitness centre, a bar, and extensive outdoor space including a terrace and garden, plus on-site activities such as table tennis and darts.

This Montgomery holiday home is situated in a rural area, approximately 4.8km from City Winery Hudson Valley and within 9.6km of Highland Lakes State Park and Thomas Bull Memorial Park.
This 465 square metre property boasts six bedrooms, five bathrooms, sleeps fifteen guests, and includes a Jacuzzi, spa, fitness centre, tennis court, and a fully equipped kitchen; nearby activities include wine tasting and outdoor recreation.

This six-bedroom Bloomingburg house, situated on a mountainside, is approximately 5km from Bloomingburg Village Hall and Wurtsboro Ridge State Forest, and 10km from Mamakating Farmers Market and Veteran's Memorial Park.
The 297 square metre property offers spacious family accommodation for up to 18 guests, boasting a fully equipped kitchen, terrace, garden, and parking, alongside nearby hiking trails and local amenities.

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.

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.

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 central Middletown flat is located in the downtown district, offering easy walking access to the Middlesex County Historical Society, just 500 meters away, and close to shops and restaurants.
This one-bedroom flat accommodates two guests and includes internet, a kitchen, and air conditioning, making it a practical base for exploring Middletown's historical sites.

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).

Parkway House Goshen Bed And Breakfast Suite 2 is located in Goshen, 22.5 kilometres from Stewart International Airport, 24.1 kilometres from Metro-North Harriman Station, and 37 kilometres from Bear Mountain State Park.
This recently renovated holiday home offers 800 square meters of living space with 2 bedrooms, accommodating up to 11 guests, and features air conditioning, free WiFi, a garden, terrace, and an outdoor fireplace.

This seven-bedroom Chester, New York property is located near the United States Military Academy and Museum Village, distances to which are unspecified.
This spacious house sleeps sixteen guests, boasting a heated pool (seasonal, additional fees apply), game room with pool table, home office, extensive outdoor space, and a state-of-the-art kitchen; ample parking is available, including trailer spaces.

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 Westbrookville studio apartment is located near the Basher Kill, a short drive (approximately 3-5 km) from Bashakill Vineyards & Winery, and within 32-48 km of attractions including Resorts World Catskills and LEGOLAND New York.
The 22-square-metre self-catering apartment sleeps four guests, boasts two bedrooms, one bathroom, a kitchenette with an air fryer and Keurig, a terrace, and access to on-site parking, a spa, and a charcoal grill; fishing and hiking trails are also nearby.

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 Bloomingburg guesthouse is situated in a tranquil countryside setting, a 16km drive from Highway 20 and within a 32km radius of Woodbury Common Premium Outlets, Bethel Woods Center for the Arts, and other attractions.
The self-catering property boasts three bedrooms, two bathrooms, sleeping up to six guests, and features a fully equipped kitchen, spacious deck with fire pit and propane grill, and convenient keypad access.

This glamping shelter is located just a short distance from Middletown, offering easy access to shops and restaurants while providing a peaceful retreat. The Woodsie - Best Glamping Experience Middletown Ny has received excellent ratings for its cleanliness, location, and overall experience.
The tent sleeps up to eight guests and features a private outdoor space with seating, hammocks, and a grill. Guests can enjoy a shared pool, discounted access to local activities, and convenient access to portable restrooms and showers.

The Eagle Eye#29 tent is located just a few kilometres from Middletown, offering easy access to shops and restaurants. The surrounding area is quiet and private, perfect for a relaxing getaway.
This one-bedroom tent sleeps up to nine guests and features modern amenities like solar electricity, a grill, fire pit, picnic table, and hammock. Guests can also enjoy the on-site swimming pool and jacuzzi.