Vacation Rentals in Middletown, NY

This house is located in the mountains of New Hampton, just 6 miles from Pine Island Town Park and Scenic Farms Golf Course, and within 9 miles of Soons Orchards and Warwick Valley Winery and Distillery. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This 4-bedroom property can accommodate up to 8 guests, with a spacious 386 square metres of living space. Guests can enjoy a range of amenities including a private pool, sauna, fitness centre, and tennis court, as well as a fully equipped kitchen, a fireplace, and a terrace.

This family-friendly villa is located in downtown Middletown, waterfront, 24 kilometres from Highland Lake and 19 kilometres from Paramount Theatre.
This expansive property offers accommodation for up to 24 guests across 7 bedrooms and 8 bathrooms, featuring a private swimming pool, hot tub, and on-site activities such as kayaking and table tennis.

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 Scotchtown lakefront apartment, situated approximately 320 kilometres from Manhattan and near Goshen's Heritage Trail and Harness Racing Museum, offers a unique Hudson Valley escape.
The self-contained flat boasts one bedroom, one bathroom, sleeping two guests, and includes a fully equipped kitchen with dishwasher, air conditioning, parking, on-site amenities such as a barbecue, fire pit, and access to canoes and paddleboats, plus three friendly horses on the 7-acre farm.

This studio apartment is located in downtown Middletown, a short walk from Clemson Bros Brewery and within easy reach of Touro College, Garnet Health, and the Paramount Theatre.
This 23 square meter self-contained flat offers accommodation for two guests with a kitchenette, dedicated workspace with Wi-Fi, and private parking, ideal for extended stays with shared laundry facilities on site.

This studio flat is located in downtown Middletown, within the revitalised Columbus Hotel, offering convenient access to the Paramount Theatre, Touro, and Garnet Health, all within 1 kilometre.
This 26 square metre studio offers a cook-ready kitchen, private bathroom, and accommodates two guests with a queen bed, featuring smart-lock self check-in and complimentary private parking across the street.

This 9-person glamping tent, the 'Dreamweaver', is located in a quiet, private setting near Scotchtown, a few minutes' drive from Middletown, offering easy access to Legoland and local wineries.
The self-catering dwelling boasts a bedroom, bathroom, solar electricity, on-site grill, fire pit, hammock, shared pool access, and discounted entry to a ropes course, camo run tube ride, and paintball activities, accommodating up to nine guests and welcoming pets for an additional fee.

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 studio flat is located in downtown Middletown, offering convenient access to local dining, Touro College, Garnet Health, and the Paramount Theatre, all within easy walking or short driving distance.
This 21 square meter flat accommodates two guests and features a kitchenette with a fridge and microwave oven, air conditioning, a private balcony, and dedicated parking, with shared laundry facilities available.

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 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 studio apartment is located in downtown Middletown's revitalised Columbus Hotel, offering convenient access to the Paramount Theatre, Touro College, and Garnet Health.
This 23 square meter studio, ideal for two guests, features a cook-ready kitchen with a fridge and microwave, air conditioning, and a terrace, with smart-lock check-in and shared laundry facilities available.

This secluded dwelling is situated in Scotchtown, just a short drive from the city centre. The surrounding area is peaceful and tranquil, with the chance to spot deer grazing nearby.
The Bluebird#4 A Magical Site! tent offers a unique accommodation experience for up to nine guests. The site boasts a swimming pool, jacuzzi, and parking, as well as easy access to Adventureland for daytime activities.

This restored 1800s farmhouse in Westtown, situated on nearly 5 bucolic acres with a private pond, offers waterfront access and is located 8 kilometres from LEGOLAND® New York, 11 kilometres from Mountain Creek Ski Resort, and 7 kilometres from Ochs Orchard.
This spacious 334 square meter residence accommodates up to 10 guests with 4 bedrooms and 4 bathrooms, featuring a private hot tub, in-ground pool, and a dedicated workout room, all within a pet-friendly environment that includes 'All-Risk' Damage Protection.

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 secluded five-bedroom house sits on a hilltop in Middletown, just 1.5 hours from New York City, offering a tranquil escape from the hustle and bustle. The property is surrounded by centuries-old stone walls and trees, creating a peaceful ambiance.
The spacious property comfortably accommodates up to 14 guests, with a variety of sleeping arrangements to suit different needs. The house features modern amenities, a large garden, a swimming pool, and a jacuzzi, ensuring a comfortable and enjoyable stay.