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32 Apartments or condos in Middletown, NY
Middletown, NY
07/22 – 07/26
$433/nighttotal: $1732 (4 )
House Near Legoland, Farms, And Airport/ Train
3 2
apartment , Scotchtown
This 3-bedroom, 1-bathroom rental unit is located in Scotchtown, offering proximity to Legoland and convenient access to Hudson Valley attractions, including a Metro-North station and Stewart Airport. This pet-friendly apartment accommodates up to 4 guests and features a full kitchen, air conditioning, and parking, with opportunities for fruit picking and hiking nearby.
Middletown, NY
07/22 – 07/26
$175/nighttotal: $700 (4 )
Columbus 402
1 2
apartment , Middletown
This one-bedroom, one-bathroom apartment in Middletown offers a convenient base with easy access to public transportation and local attractions. This unit accommodates up to two guests and features air conditioning, internet, and a full kitchen for a comfortable stay.
9.8 7 reviews
Middletown, NY
08/28 – 09/05
$299/nighttotal: $2392 (8 )
Hike & Fish: Outdoor Retreat Near Trails
1 3
apartment , Otisville
This Westbrookville apartment, near the Basher Kill and a short walk from hiking trails in the Bashakill Wildlife Management Area, is conveniently located approximately 29 miles from Minnewaska State Park Preserve and LEGOLAND New York. This 840-square-foot rental boasts two bedrooms, one bathroom, sleeps four guests, and includes a deck with a gas grill, a kitchenette, free Wi-Fi, air conditioning, and on-site parking; fishing and outdoor recreation are readily accessible.
9.1 52 reviews
Middletown, NY
08/21 – 08/23
$375/nighttotal: $750 (2 )
Cozy Apartment Near Legoland!
1 5
apartment , Goshen
This Goshen apartment is conveniently located near Legoland, just minutes away from Woodbury Common outlets and Bear Mountain, offering easy access to popular attractions and shopping. This rental consistently receives excellent ratings for location, cleanliness, and overall user experience. The apartment comfortably accommodates up to six guests with two full beds, a queen bed, a sofa, and a futon. Guests can enjoy modern amenities such as a flat-screen TV, a fully equipped kitchen, and bathroom essentials, all while enjoying a relaxing vacation near Legoland.
9.3 25 reviews
Middletown, NY
08/28 – 09/05
$257/nighttotal: $2056 (8 )
Cozy Delight
1 3
apartment , Scotchtown
This Scotchtown house rental near Middletown, NY, offers convenient proximity to Middletown's shopping mall and a major hospital. The three-bedroom, one-bathroom home sleeps four guests and includes a kitchen with a fridge, freezer, and microwave, air conditioning, a garden, parking, and internet access.
Middletown, NY
08/28 – 09/05
$252/nighttotal: $2016 (8 )
Close To Trails: Studio W/ Water Views
1 3
apartment , Otisville
This apartment in Westbrookville offers proximity to nature and local attractions, being a 5-minute walk from Gobbler's Knob State Forest and Sheriff H. Frank Bigger Memorial Park, and within 3 miles of Bashakill Vineyards and Otisville Veterans Memorial Park. Enjoy a private balcony, complimentary WiFi in public areas, on-site barbecue grills, and free self-parking at this Otisville rental.
8.0 2 reviews
Middletown, NY
08/21 – 08/23
$522/nighttotal: $1044 (2 )
Hike, Ski & Explore: Otisville Retreat W/ Yard!
4 5
apartment , Otisville
This spacious 193 m² vacation home in Mount Hope is situated a 14-minute walk from Otisville Veterans Memorial Park and a 2-minute drive from Mount Hope Town Park. This family-friendly apartment offers four bedrooms, three bathrooms, a fully equipped kitchen, air conditioning, a fireplace, a private garden with a fire pit and barbecue, and in-unit laundry.
9.5 4 reviews
Middletown, NY
08/21 – 08/23
$343/nighttotal: $686 (2 )
Cozy Delight Home
1 5
apartment , Scotchtown
This Scotchtown apartment rental, centrally located in Scotchtown, offers easy access to local attractions—though specific distances require further clarification. The 3-bedroom, 1-bathroom unit sleeps 6, features a king-size bed in one bedroom, and includes amenities such as internet, air conditioning, a kitchen, parking, and a fitness center; further details on the apartment's size, specific layout, and nearby activities are needed.
10 8 reviews
Middletown, NY
08/28 – 09/05
$377/nighttotal: $3016 (8 )
Serene Rustic Retreat With Lake
3 3
cabin , Otisville
This lakeside Otisville cabin offers four bedrooms and three bathrooms, sleeping up to six guests, and is located within three miles of Gobbler's Knob State Forest, Otisville Veterans Memorial Park, and Delaware & Hudson Canal County Park. The 4-bedroom, 3-bathroom vacation rental boasts a fully equipped kitchen with a dishwasher, a fireplace, a balcony, and a private garden; nearby water activities and on-site parking are also available.
9.4 13 reviews
Middletown, NY
08/21 – 08/23
$453/nighttotal: $906 (2 )
Blooming Tranquil Getaway
1 5
apartment , Bloomingburg
This Bloomingburg apartment rental is conveniently located a ten-minute drive from NY State Route 20, offering easy access to attractions like Woodbury Common Premium Outlets, Bethel Woods Center for the Arts, Legoland New York, and various casinos within a 20-mile radius. The spacious bi-level unit features three bedrooms sleeping up to six guests, two bathrooms, a fully equipped kitchen with dishwasher, a private garden with a deck, fire pit, and propane grill, plus keyless entry and free parking.
9.7 23 reviews
Middletown, NY
08/28 – 09/05
$409/nighttotal: $3272 (8 )
Lake Trail Retreat
1 3
apartment , Otisville
This Otisville house rental is conveniently located near Middletown, a short 5-minute walk from a scenic lake trail and a 20-minute drive from Legoland New York. The three-bedroom, two-bathroom home sleeps eight guests and boasts a fully equipped kitchen with dishwasher, 65" smart TVs in each bedroom, a garden, parking, and security features including a Ring doorbell and floodlight camera.
9.8 10 reviews
Middletown, NY
08/28 – 09/05
$202/nighttotal: $1616 (8 )
Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, Ny
1 3
apartment , Chester
This Chester, NY vacation rental is conveniently located near The Rock Sports Complex (4-minute drive), Wickham Lake (5-minute drive), LEGOLAND® New York (8-minute drive), and Woodbury Common Premium Outlets (14-minute drive), offering easy access to outdoor recreation and shopping. This one-bedroom, one-bathroom apartment sleeps four guests and includes Wi-Fi, air conditioning, and essential amenities.
Check Out Family Apartments in Middletown, NY
Traveling to Middletown, NY with kids? A quality family vacation apartment keeps city attractions within easy reach for the whole group.
9.8 80 reviews
Middletown, NY
08/28 – 09/05
$309/nighttotal: $2472 (8 )
Historic Meets Modern 1900 Farmhouse Plus
1 3
apartment , Washington Heights
This historic farmhouse is located in Middletown, New York, just 90 minutes from Manhattan via express bus and surrounded by the scenic Hudson Valley. The property has earned excellent ratings for its cleanliness, location, and overall experience. The farmhouse has four bedrooms and two bathrooms, comfortably accommodating up to seven guests. Enjoy a fully equipped kitchen, air conditioning, a garden, and two decks for relaxing and enjoying the surrounding nature.
9.8 98 reviews
Middletown, NY
07/22 – 07/26
$236/nighttotal: $944 (4 )
Great Goshen Get-away Close To Legoland!
2 2
apartment , Goshen
This spacious apartment is ideally located in Goshen, just a short drive from Legoland New York, Woodbury Commons Shopping Outlets, and Bear Mountain State Park. It consistently receives excellent ratings for its cleanliness, location, and overall user experience. The apartment offers two separate units combined, providing four bedrooms, two kitchens, and two bathrooms, perfect for large families or groups. It includes a dedicated game room, modern amenities, and easy access to a variety of attractions, shopping, and outdoor activities.
9.5 150 reviews
Middletown, NY
07/22 – 07/26
$437/nighttotal: $1748 (4 )
Beautiful Log Cabin Style House
1 2
apartment , Scotchtown
This log cabin-style apartment is located just minutes from Middletown, offering easy access to major shopping areas and restaurants. The apartment has received excellent ratings for location, cleanliness, and user experience. The apartment features three bedrooms and one bathroom, comfortably accommodating up to 12 guests. Amenities include a private sauna, a swimming pool, a fire pit, a large deck, and a variety of entertainment options like a video game, popcorn and slush machines, and access to discounted activities at the nearby Ring Homestead Adventure Camp.
10 5 reviews
Middletown, NY
08/28 – 09/05
$387/nighttotal: $3096 (8 )
Serene And Modern Woodland Retreat, Hudson Valley & Catskills
3 3
apartment , Montgomery
This Montgomery, New York vacation rental is conveniently located a short drive from LEGOLAND® New York (21 minutes) and Angry Orchard (11 minutes). The three-bedroom, two-bathroom house sleeps six guests and features a fully equipped kitchen, laundry facilities, a private garden with patio and barbecue, and amenities including Wi-Fi, a fireplace, and on-site parking.
Best Middletown, NY apartment rentals with a kitchen
Middletown, NY
07/22 – 07/26
$492/nighttotal: $1968 (4 )
Family Getaway Near Hudson Valley Attractions
1 2
apartment , Mechanicstown
This Mechanicstown rental unit offers a peaceful retreat in a quiet neighborhood, providing convenient access to Hudson Valley attractions. This 3-bedroom, 1-bathroom apartment accommodates up to 4 guests and features a fully equipped kitchen, air conditioning, complimentary parking, and easy self-check-in for a comfortable stay.
9.3 3 reviews
Middletown, NY
07/22 – 07/26
$175/nighttotal: $700 (4 )
The Columbus Hotel | The Canopy Studio | 52-301
1 2
apartment , Middletown
This apartment is located in a central Middletown district, offering easy access to local shops and dining establishments. This accommodation offers a kitchen, air conditioning, and internet for up to 2 guests, serving as a convenient base for exploring Middletown.
Middletown, NY
08/28 – 09/05
$523/nighttotal: $4184 (8 )
Elegant Town Home Middletown Suburb Close To City
3 3
apartment , Washington Heights
This modern vacation rental is located in Middletown, New York, just a short drive from Washington Heights and its attractions like the Paramount Theatre and Museum Village. The house offers a comfortable and relaxing escape from the city, with easy access to local wineries, breweries, and historical sites. The three-bedroom, three-bathroom home provides plenty of space for families or groups. Enjoy modern appliances, a Jacuzzi, and a private parking space.
10 5 reviews
Middletown, NY
07/22 – 07/26
$175/nighttotal: $700 (4 )
Cozy Downtown Studio W/ Kitchen & Workspace
1 2
apartment , Middletown
This studio suite is centrally located in Middletown's downtown district, offering convenient access to dining, cafes, breweries, and essential services, with proximity to Touro College and Garnet Health Medical Center. This apartment features a fully equipped kitchen with modern appliances, air conditioning, free on-site parking, and accommodates up to 2 guests with self-check-in via a smart lock.
Frequently Asked Questions about apartment rentals in Middletown, NY
What are the top cultural and historical sites in Middletown, NY?
The Middletown Thrall Library is a beautiful historic building with a rich collection of books and archives. The Orange County Historical Society Museum showcases the region's history, including exhibits on local industries and the Underground Railroad.
Middletown is known for its rich history, being a key stop on the Underground Railroad. It's also a great location for outdoor recreation, with the Walkway Over the Hudson State Historic Park and the Minisink Valley Rail Trail nearby.
What are the best apartments with a pool in Middletown, NY?
Where can you find the best local markets and street food in Middletown, NY?
The Middletown Farmers Market is a great place to find fresh produce, local crafts, and tasty treats. You can also find a variety of street food vendors at the Middletown City Hall Plaza during special events.
What are the best apartments with a jacuzzi in Middletown, NY?
How is the public transportation system in Middletown, NY?
Middletown has a public bus system operated by Mid-Hudson Valley Transit. You can find bus stops throughout the city, and routes connect to neighboring towns and cities.
What are the best apartments for families and kids in Middletown, NY?
Which seasonal events or festivals should apartment renters look forward to in Middletown, NY?
The Middletown Summerfest is a popular annual event with live music, food vendors, and family-friendly activities. The Middletown Fall Festival is another great celebration, featuring a parade, craft vendors, and live entertainment.
What are the best pet friendly apartments in Middletown, NY?
What amenities are typically included in apartments in Middletown, NY?
Most apartments in Middletown include basic amenities like central air conditioning, heat, and on-site laundry facilities. Some apartments may also offer additional amenities such as parking, a fitness center, or a swimming pool.
What are the best apartments with parking in Middletown, NY?
What leisure activities are available for relaxation in Middletown, NY?
For relaxation, you can enjoy a walk or bike ride on the Minisink Valley Rail Trail, which runs along the beautiful Wallkill River. The Walkway Over the Hudson State Historic Park also offers stunning views and walking paths.
Destinations nearby
Best Middletown, NY apartment rentals with air conditioning
9.9 174 reviews
Middletown, NY
08/28 – 09/05
$186/nighttotal: $1488 (8 )
Just Around The Corner
1 3
apartment , Scotchtown
This one-bedroom apartment is conveniently located in Scotchtown, just a short drive from Middletown, Legoland, Wallkill, and Warwick, offering easy access to local attractions. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The apartment comfortably sleeps six guests and features a private bedroom with a queen bed, a pull-out queen sleeper sofa, and a Murphy bed. The apartment includes a fully equipped kitchen, a private patio, and a washer and dryer for added convenience.
Middletown, NY
08/28 – 09/05
$266/nighttotal: $2128 (8 )
Pool House On A Park-like Estate, Pet Friendly, 7 Min To Legoland.
1 3
apartment , Goshen
This one-bedroom vacation rental is conveniently located in Goshen, just a short drive from popular attractions like LEGOLAND® New York and the Harness Racing Museum and Hall of Fame. The house offers easy access to both the excitement of the city and the tranquility of nearby Sterling Forest State Park. This cozy rental comfortably sleeps four guests and features modern amenities including free Wi-Fi, air conditioning, a swimming pool, and a washer and dryer. Enjoy a relaxing vacation with the convenience of essential supplies provided, and explore the nearby attractions like the Paramount Theatre, Museum Village, and Soons Orchards.
9.5 110 reviews
Middletown, NY
07/22 – 07/26
$173/nighttotal: $692 (4 )
Groovy Digs For A Unique Stay On Murray Hill
1 2
apartment , Goshen
This Goshen apartment is located in a quiet residential area, just a short walk from the downtown district's shops, restaurants, and theaters. It has consistently received excellent ratings for cleanliness, location, and overall user experience. The apartment comfortably accommodates two guests and features a fully equipped kitchen and bathroom. Enjoy amenities like a private patio with a grill and fire pit, a unique bar with pinball machines and a dartboard, and a multipurpose room with a queen-size Murphy bed.
Middletown, NY
08/28 – 09/05
$1140/nighttotal: $9120 (8 )
Pond + Gazebo: Expansive Hudson Valley Escape!
6 3
apartment , Goshen
This 6-bedroom, 4-bathroom vacation home in Goshen is a 3-minute drive from the Goshen Historic Track and the Harness Racing Museum and Hall of Fame. This 4390-square-foot property accommodates up to 14 guests and features a private garden with a fire pit, a barbecue, internet, a TV with a video library, video games, a fireplace, air conditioning, and laundry facilities, with proximity to hiking, basketball, LEGOLAND® New York, and the Orange County Arboretum.
Explore Pet-Friendly Apartments in Middletown, NY
A quality pet-friendly vacation apartment in Middletown, NY means nearby dog parks and city walks are just steps away from your front door.
10 8 reviews
Middletown, NY
08/28 – 09/05
$377/nighttotal: $3016 (8 )
Serene Rustic Retreat With Lake
3 3
cabin , Otisville
This lakeside Otisville cabin offers four bedrooms and three bathrooms, sleeping up to six guests, and is located within three miles of Gobbler's Knob State Forest, Otisville Veterans Memorial Park, and Delaware & Hudson Canal County Park. The 4-bedroom, 3-bathroom vacation rental boasts a fully equipped kitchen with a dishwasher, a fireplace, a balcony, and a private garden; nearby water activities and on-site parking are also available.
Middletown, NY
07/22 – 07/26
$492/nighttotal: $1968 (4 )
Family Getaway Near Hudson Valley Attractions
1 2
apartment , Mechanicstown
This Mechanicstown rental unit offers a peaceful retreat in a quiet neighborhood, providing convenient access to Hudson Valley attractions. This 3-bedroom, 1-bathroom apartment accommodates up to 4 guests and features a fully equipped kitchen, air conditioning, complimentary parking, and easy self-check-in for a comfortable stay.
9.5 150 reviews
Middletown, NY
07/22 – 07/26
$437/nighttotal: $1748 (4 )
Beautiful Log Cabin Style House
1 2
apartment , Scotchtown
This log cabin-style apartment is located just minutes from Middletown, offering easy access to major shopping areas and restaurants. The apartment has received excellent ratings for location, cleanliness, and user experience. The apartment features three bedrooms and one bathroom, comfortably accommodating up to 12 guests. Amenities include a private sauna, a swimming pool, a fire pit, a large deck, and a variety of entertainment options like a video game, popcorn and slush machines, and access to discounted activities at the nearby Ring Homestead Adventure Camp.
8.0 2 reviews
Middletown, NY
08/21 – 08/23
$522/nighttotal: $1044 (2 )
Hike, Ski & Explore: Otisville Retreat W/ Yard!
4 5
apartment , Otisville
This spacious 193 m² vacation home in Mount Hope is situated a 14-minute walk from Otisville Veterans Memorial Park and a 2-minute drive from Mount Hope Town Park. This family-friendly apartment offers four bedrooms, three bathrooms, a fully equipped kitchen, air conditioning, a fireplace, a private garden with a fire pit and barbecue, and in-unit laundry.