Compare Vacation Rentals & Airbnb in Middletown, NY
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29 Rentals and Airbnb in Middletown, NY
9.6 15 reviews
Middletown, NY
22/07 – 26/07
$142/nighttotal: $568 (4 )
Waterlily-best Glamping Experience, Middletown Ny
1 2
glamping , Scotchtown
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.
9.1 52 reviews
Middletown, NY
21/08 – 23/08
$524/nighttotal: $1048 (2 )
Cozy Apartment Near Legoland!
1 5
apartment , Goshen
This two-bedroom apartment is located just a few kilometres from Legoland, making it perfect for families visiting Goshen. The apartment has received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay. The apartment can comfortably accommodate up to six guests and is equipped with a fully equipped kitchen, bathroom essentials, and a flat-screen TV. Guests can enjoy easy access to nearby restaurants, shops, and attractions like Woodbury Common outlets and Bear Mountain, offering a range of shopping and outdoor activities.
Middletown, NY
21/08 – 23/08
$439/nighttotal: $878 (2 )
Quaint 2 Bedroom Bungalow On 225 Acre Farm
1 5
gîte , Goshen
This charming two-bedroom cottage is situated on a sprawling 227-acre farm, just a short drive from the centre of Goshen and its historic attractions. The peaceful countryside setting offers a tranquil escape from the hustle and bustle of city life. The cottage comfortably sleeps six guests and is equipped with a kitchen, air conditioning, and parking. Guests can enjoy fresh produce from the farm, interact with animals, and explore the surrounding countryside.
10 1 review
Middletown, NY
22/07 – 26/07
$1013/nighttotal: $4052 (4 )
A Hudson Valley Barn Celebration
1 2
farm , Middletown
This Middletown farmhouse, sleeping up to 16 guests, is situated in [Insert District Name, Middletown] – precise location details upon request. The 6-bedroom, 4-bathroom property boasts a fully equipped kitchen, Jacuzzi, fitness centre, and garden, offering ample space and modern amenities for a comfortable stay.
9.7 28 reviews
Middletown, NY
22/07 – 26/07
$288/nighttotal: $1152 (4 )
Great Small Barn
1 2
farm , Goshen
This renovated 1864 barn, located in Goshen's historic district, offers a unique stay within walking distance of Goshen's village centre, restaurants, and an ice cream parlour, and adjacent to a 32+ kilometre biking and walking trail. The self-catering property features an open-plan living, dining, and kitchen area with modern appliances, a newly remodelled bathroom, private parking, and a private tennis and pickleball court; it sleeps two guests.
9.5 21 reviews
Middletown, NY
22/07 – 26/07
$501/nighttotal: $2004 (4 )
The Cottage Farmhouse
1 2
farm , Middletown
This charming farm stay is situated in Middletown, just a short distance from the town's main attractions and historical landmarks. It enjoys excellent ratings for cleanliness, location and user experience. This welcoming property can accommodate up to six guests and features a fully equipped kitchen, a comfortable living area, two bathrooms and a lovely garden. Guests can enjoy a range of amenities, including internet access, air conditioning, parking and a fitness centre.
9.4 13 reviews
Middletown, NY
21/08 – 23/08
$632/nighttotal: $1264 (2 )
Blooming Tranquil Getaway
1 5
apartment , Bloomingburg
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.
9.7 24 reviews
Middletown, NY
21/08 – 23/08
$674/nighttotal: $1348 (2 )
Lake Trail Retreat
1 5
apartment , Otisville
This three-bedroom house near Middletown, New York, offers easy access to Legoland New York (approximately 32km away) and a scenic lake trail just an 800-metre walk from the property. The 3-bedroom property sleeps eight guests, features a fully equipped kitchen with dishwasher, king and queen-sized beds, 65" smart TVs in each bedroom, a garden, parking, and air conditioning; future additions include a games room and a renovated master bathroom.
10 6 reviews
Middletown, NY
22/07 – 26/07
$159/nighttotal: $636 (4 )
9 Person Glamping Tent- Dreamweaver
1 2
glamping , Scotchtown
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.
9.7 13 reviews
Middletown, NY
22/07 – 26/07
$139/nighttotal: $556 (4 )
9 Person Glamping Tent- Chipmunk
1 2
glamping , Scotchtown
Chipmunk Cove#26 is situated in Scotchtown, just a short distance from Legoland and other attractions. This accommodation receives excellent ratings for location, cleanliness, and user experience. The tent offers a spacious layout, accommodating up to 45 guests, making it perfect for large groups. Amenities include picnic tables, BBQ grills, a fridge, and a bonfire pit, alongside access to Adventureland for additional entertainment.
9.1 15 reviews
Middletown, NY
22/07 – 26/07
$252/nighttotal: $1008 (4 )
Studio Chic In The City
1 2
apartment , Middletown
This Middletown studio flat is centrally located in the town centre, offering easy access to Middletown's restaurants, shops, and entertainment venues. The self-contained apartment sleeps two, features a fully equipped kitchen with fridge, freezer, and microwave, a queen-size bed, and free Wi-Fi; on-site parking is also available.
9.3 3 reviews
Middletown, NY
21/08 – 23/08
$4905/nighttotal: $9810 (2 )
Welcome To The Farmhouse At The Barn!
1 5
gîte , Scotchtown
This farmhouse gîte in the Hudson Valley is conveniently located near attractions like Legoland and the Renaissance Faire, offering a scenic escape in a tranquil setting. It has consistently received excellent ratings for its cleanliness, location, and overall experience. This charming holiday home sleeps up to 16 guests in 8 bedrooms and 4 bathrooms. It features modern amenities, including air conditioning, a well-equipped kitchen, a garden, and ample parking. Enjoy the rustic charm and modern comforts, while exploring the Hudson Valley's wineries, breweries, and restaurants.
Best family friendly Middletown, NY vacation rentals
Among the 29 accommodations in Middletown, NY, here are the 4 best family friendly rentals
9.8 98 reviews
Middletown, NY
21/08 – 23/08
$516/nighttotal: $1032 (2 )
2 Unit Condo Minutes From Lego Land
2 5
apartment , Goshen
This apartment is conveniently located in Goshen, just a short drive from Legoland New York, Woodbury Commons Shopping Outlets, and Bear Mountain State Park. It has consistently received excellent ratings for its cleanliness, location, and overall user experience. The property features two separate units, providing flexibility and privacy for guests. Each unit is equipped with modern amenities, including a fully equipped kitchen, air conditioning, and parking, as well as a dedicated game room for entertainment.
8.0 2 reviews
Middletown, NY
21/08 – 23/08
$730/nighttotal: $1460 (2 )
Hike, Ski & Explore: Otisville Retreat W/ Yard!
4 5
apartment , Otisville
This family-friendly apartment in Mount Hope, Otisville, is a 14-minute walk from Otisville Veterans Memorial Park and a 2-minute drive from Mount Hope Town Park. This 193 m² holiday home offers four bedrooms, three bathrooms, air conditioning, a fireplace, and a fully equipped kitchen, with a private garden featuring a fire pit and barbecue for your convenience.
9.7 64 reviews
Middletown, NY
22/07 – 26/07
$192/nighttotal: $768 (4 )
Victor-amazing Glamping Experience-middletown Ny
1 2
glamping , Scotchtown
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.
9.5 150 reviews
Middletown, NY
21/08 – 23/08
$561/nighttotal: $1122 (2 )
Beautiful Log Cabin Style House
1 5
apartment , Scotchtown
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.
Best Middletown, NY vacation rentals with parking
Middletown, NY
21/08 – 23/08
$2119/nighttotal: $4238 (2 )
Pool, Fire Pit Bedroom & Alaska King Sleeps 16
5 5
house , Chester
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.
Middletown, NY
27/06 – 04/07
$718/nighttotal: $5026 (7 )
Elegant Town Home Middletown Suburb Close To City
3 2
apartment , Washington Heights
This modern house is situated in Middletown, New York, just a short drive from Washington Heights and its attractions. The surrounding area offers a peaceful change of pace, with vineyards, breweries, and historical sites close by. This three-bedroom, three-bathroom property provides spacious and comfortable accommodation for your stay. The house is fully equipped with modern amenities, including air conditioning, a Jacuzzi, and parking, as well as travel brochures to help you explore the local area.
9.6 20 reviews
Middletown, NY
27/06 – 04/07
$299/nighttotal: $2093 (7 )
Escape To A Streamside Cabin In The Lower Catskills
1 2
cabin , Wurtsboro
This Wurtsboro cottage is conveniently located less than 1.6km from Veteran's Memorial Park and the Mamakating Library, and within 3.2km of Sullivan County Parks & Recreation and the Mamakating Farmers Market. The 42-square-metre self-catering lodge sleeps two guests, boasting a fully equipped kitchen, a washing machine, a fireplace, a Smart TV, and a barbecue; enjoy the smoke-free environment and excellent user ratings.
10 6 reviews
Middletown, NY
22/07 – 26/07
$584/nighttotal: $2336 (4 )
Hudson Valley Horse Farm Stay | 10 Min To Legoland
1 2
gîte , Scotchtown
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.
Frequently Asked Questions about vacation rentals in Middletown, NY
What are the top family-friendly attractions in Middletown, NY?
The Middletown Thrall Library is a fantastic place for families, with fun events and activities for kids. Also, the Orange County Arboretum is a great place for a family stroll, with plenty of space to run around.
What are the best Airbnb and vacation rentals in Middletown, NY?
When is the best time to book a vacation rental in Middletown, NY?
It's best to book your vacation rental in Middletown during the shoulder seasons, from April to May or September to October. You'll avoid the crowds and still enjoy pleasant weather.
What are the most popular Airbnbs in Middletown, NY?
What are the best budget-friendly activities in Middletown, NY?
The Walkway Over the Hudson State Historic Park is free to enter and offers breathtaking views. You can also enjoy a picnic in the Orange County Arboretum or explore the Middletown Thrall Library.
What are the best vacation rentals with a pool in Middletown, NY?
What are the best walking or cycling routes in Middletown, NY?
The Walkway Over the Hudson State Historic Park is a fantastic walking and cycling route, offering stunning views of the Hudson River. You can also try the Wallkill Valley Rail Trail for a scenic ride.
What are the best rentals or Airbnbs with a jacuzzi in Middletown, NY?
Are there pet-friendly attractions in Middletown, NY?
The Orange County Arboretum is a great place to bring your furry friend for a walk. The Walkway Over the Hudson also welcomes dogs on leash.
What are the benefits of choosing a vacation rental in Middletown, NY?
Vacation rentals offer more space and privacy compared to hotels, and often come with kitchen facilities for preparing meals. They can also be a more affordable option, especially for larger groups.
What are the top sports attractions and facilities in Middletown, NY?
Middletown is home to the Middletown High School Athletic Complex, which hosts various sporting events and offers facilities for different sports. You can also check out the Middletown YMCA for fitness classes and activities.
Destinations nearby
Best Middletown, NY vacation rentals with a balcony
Middletown, NY
22/07 – 26/07
$885/nighttotal: $3540 (4 )
Lakefront Cottage 10 Min To Legoland Farmstay
1 2
cottage , Mechanicstown
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).
Best pet friendly Middletown, NY vacation rentals
Among the 29 accommodations in Middletown, NY, here are the 4 best pet friendly rentals
9.5 4 reviews
Middletown, NY
22/07 – 26/07
$894/nighttotal: $3576 (4 )
The Cathedral Barn
3 2
farm , Middletown
This Middletown farm stay, offering both the entire property and a Farmhouse Cottage, is situated in a rural area of Middletown; precise location details within the town are unavailable, but proximity to other rentals suggests a countryside setting. Sleeping up to eight guests, the property boasts three bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher, air conditioning, a garden, a fitness centre, and free parking; pets are welcome, and an age restriction applies (40+ or under 40 with adult supervision).
Middletown, NY
21/08 – 23/08
$720/nighttotal: $1440 (2 )
Hike, Ski & Explore: Otisville Retreat W/ Yard!
1 5
house , Otisville
This Otisville property is located 43 kilometres from Mohonk Preserve and 48 kilometres from Metro-North Harriman Station, with DM Weil Gallery and Stewart International Airport both 43 kilometres away. This spacious 193 square metre house offers accommodation for 13 guests with 4 bedrooms and 3 bathrooms, featuring air conditioning, WiFi, a fully equipped kitchen with a dishwasher and oven, and a garden, making it ideal for outdoor enthusiasts with nearby hiking and skiing.
Middletown, NY
22/07 – 26/07
$605/nighttotal: $2420 (4 )
House Near Legoland, Farms, And Airport/ Train
3 2
apartment , Scotchtown
This family-friendly flat in Scotchtown is ideally positioned for exploring the Hudson Valley, located just 8 kilometres from Legoland New York and offering convenient access to the Metro-North train station and Stewart International Airport for straightforward travel. This three-bedroom flat accommodates up to four guests and features essential amenities including a kitchen, air conditioning, and parking, with nearby opportunities for fruit picking and exploring riverfront towns.
9.5 4 reviews
Middletown, NY
21/08 – 23/08
$479/nighttotal: $958 (2 )
Cozy Delight Home
1 5
apartment , Scotchtown
This three-bedroom Scotchtown apartment, perfect for families or groups of up to six, offers convenient access to local attractions, although precise distances are unspecified. The self-catering flat features a king-size bed in one bedroom, a fitness centre, parking, and internet access; further details regarding the property's size and specific interior design are unavailable.