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Middletown, NY apartments
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46 Apartments or condos in Middletown, NY

Top-Rated Apartments near the City Center in Middletown, NY

Renting a downtown vacation apartment in Middletown, NY places you steps from local dining, historic neighborhoods, and bustling city nightlife.

The Columbus Hotel | The Sunny Studio | 52-302 - Middletown, NY
9.6 11 reviews

The Columbus Hotel | The Sunny Studio | 52-302

apartment, Middletown
This Middletown studio apartment offers convenient access to Routes 17 and 84, placing you near local breweries, restaurants, and Middletown's hospital.
The unit features a queen-size bed, a compact kitchen with a fridge, freezer, and microwave, one bathroom, and accommodates two guests, perfect for exploring Legoland and Woodbury Common Premium Outlets.
The Columbus Hotel | The Upper Studio | 52-402 - Middletown, NY
8.5 4 reviews

The Columbus Hotel | The Upper Studio | 52-402

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.
The Columbus Hotel | The Market Suite | 52-202 - Middletown, NY
9.4 22 reviews

The Columbus Hotel | The Market Suite | 52-202

apartment, Middletown
This Middletown studio apartment offers a convenient downtown location, close to Middletown's restaurants and shops.
The unit features a queen-size bed, a full kitchen with a fridge, freezer, and microwave, one bathroom, free Wi-Fi, and on-site parking for guests.
The Columbus Hotel | The Reimagined Suite | 52-304 - Middletown, NY
10 1 review

The Columbus Hotel | The Reimagined Suite | 52-304

apartment, Middletown
This downtown Middletown suite, located within the revitalized Columbus Hotel, offers a private and practical stay near dining, Touro College of Osteopathic Medicine, Garnet Health Medical Center, and the Paramount Theatre.
This refreshed private suite accommodates two guests and features a full-size refrigerator, convection cooktop, sink, kitchenware, a dedicated workstation, Smart TV, and shared laundry facilities, with weekly and monthly stays welcome.

Best Middletown, NY apartment rentals with air conditioning

Historic Barn - 2 Bedroom Apartment Close To Legoland Ny - Middletown, NY
No reviews

Historic Barn - 2 Bedroom Apartment Close To Legoland Ny

apartment, Goshen
This historic barn rental in Goshen is located 15 miles from Metro-North Harriman Station and 14 miles from Stewart International Airport, with Mohonk Preserve 27 miles away.
This spacious 10,230 square foot accommodation accommodates up to 11 guests and features a full kitchen, air conditioning, WiFi, a spa, and on-site casino entertainment, with horse riding opportunities nearby.
Spacious Westtown Home, Firepit, Up To 10 Guest - Middletown, NY
9.6 10 reviews

Spacious Westtown Home, Firepit, Up To 10 Guest

apartment, Unionville
This Westtown vacation home in Unionville, New Jersey, is conveniently located within three miles of High Point State Park, the Minisink Heritage Museum, and Minisink Town Hall.
This three-bedroom, two-bathroom house sleeps ten guests and features a fully equipped kitchen, in-unit laundry, a fitness center, and a terrace—ideal for exploring nearby Hanson Memorial Park.
The Columbus Hotel | The Weekender Suite | 52-204 - Middletown, NY
9.3 27 reviews

The Columbus Hotel | The Weekender Suite | 52-204

apartment, Middletown
This studio apartment is located in downtown Middletown, a 1-minute walk from Clemson Bros Brewery and surrounded by dining and shopping options, with easy access to NY-17 and Route 84.
This studio offers a full kitchen, air conditioning, parking, and an on-site washer and dryer, accommodating up to two guests.
Serene And Modern Woodland Retreat, Hudson Valley & Catskills - Middletown, NY
10 5 reviews

Serene And Modern Woodland Retreat, Hudson Valley & Catskills

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.

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.
  • What are the best apartments in Middletown, NY?

  • What makes Middletown, NY unique or famous?

    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?

    Want Peace Of Mind and Palace Near Woodbury Mall 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?

    The best apartment with a jacuzzi in Middletown, NY is Elegant Town Home Middletown Suburb Close To City.

  • 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.

Popular destinations

Search Apartments with Balconies in Middletown, NY

Private balconies with city skyline views come as standard at these vacation apartments of Middletown, NY, offering a great start to any day.

Custom Log Cabin, Hot Tub, Fire Pit & Wood Stove - Middletown, NY
10 1 review

Custom Log Cabin, Hot Tub, Fire Pit & Wood Stove

apartment, Florida
Escape the Florida heat at this Upstate New York log cabin, situated on 7.4 acres two miles from Warwick, offering easy access to local wineries, breweries, and hiking trails.
This 2,700-square-foot retreat boasts four bedrooms, 2.5 bathrooms, and accommodates up to ten guests, featuring a hot tub, fire pit, and wraparound porches with mountain views.
Spacious Ada 6br Home For Groups W. Private Pond - Middletown, NY
No reviews

Spacious Ada 6br Home For Groups W. Private Pond

apartment, Chester
This ADA-friendly retreat in Goshen, Hudson Valley, is located just minutes from LEGOLAND New York Resort and Woodbury Common Premium Outlets, offering easy access to local attractions and outdoor recreation.
This spacious 6-bedroom house spans 26,240 square feet and accommodates up to 16 guests, featuring a chef's kitchen, multiple living areas including a family room with a pool table, an enclosed sunroom, and exclusive access to a private pond.
Cozy Apartment Near Legoland! - Middletown, NY
8.9 7 reviews

Cozy Apartment Near Legoland!

apartment, Middletown
This one-bedroom apartment rental in New Hampton, approximately 20 miles from Middletown, offers easy access to Legoland New York and is within 30 miles of Bear Mountain State Park and the DM Weil Gallery.
The 8,290-square-foot unit features a full kitchen, private terrace, parking, Wi-Fi, and accommodates up to nine guests.
Elegant Home W/7brs, Game Room, Luxury Yard, Pool - Middletown, NY
8.8 3 reviews

Elegant Home W/7brs, Game Room, Luxury Yard, Pool

apartment, Chester
This luxurious Chester, NY home is located near the United States Military Academy and Museum Village, offering easy access to local attractions.
This seven-bedroom, 6-bathroom house, sleeping up to 16 guests, boasts a heated pool, game room, home office, and state-of-the-art kitchen with multiple dining areas.

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.

The Reservoir Home Near Winery’s And Legoland - Middletown, NY
9.8 89 reviews

The Reservoir Home Near Winery’s And Legoland

apartment, Goshen
The Reservoir Retreat is located in a peaceful Goshen neighborhood, just five minutes from the village center and Legoland. The property has earned excellent ratings for its location, cleanliness, and overall experience.
This four-bedroom, two-bathroom house can comfortably accommodate up to 10 guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, and internet access. Enjoy the serene pond and fountain in the backyard, explore the surrounding woods for wildlife viewing, and take advantage of the proximity to local attractions like Chester, breweries, wineries, and apple orchards.
The Wooden Igloo Near Legoland Ny - Middletown, NY
10 22 reviews

The Wooden Igloo Near Legoland Ny

apartment, Middletown
The Wooden Igloo, a unique one-bedroom apartment rental near Middletown, New York, offers a secluded yet convenient location, just 9 miles from LEGOLAND New York and within a short drive of Soons Orchards and other attractions.
This luxurious 1-bedroom rental boasts 3 bathrooms, sleeps 12 guests, includes a fully equipped kitchen, air conditioning, a swimming pool, parking, and internet access, promising a memorable getaway.
Serene Rustic Retreat With Lake - Middletown, NY
10 8 reviews

Serene Rustic Retreat With Lake

apartment, 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.
Blooming Bnb (Close To Lego Land &Much More) - Middletown, NY
9.5 15 reviews

Blooming Bnb (Close To Lego Land &Much More)

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.

Guest-Favorite Apartments with Parking in Middletown, NY

Park your car and enjoy the city center; each of these vacation apartments in Middletown, NY comes with a free on-site parking spot.

The Cozy Goshen Home, 5mins From Legoland And Near Skiing! - Middletown, NY
10 22 reviews

The Cozy Goshen Home, 5mins From Legoland And Near Skiing!

apartment, Goshen
The Columbus Hotel | The Courtyard Suite | 89-303 - Middletown, NY
9.3 11 reviews

The Columbus Hotel | The Courtyard Suite | 89-303

apartment, Middletown
The Columbus Hotel | Four-poster Suite | 52-203 - Middletown, NY
8.4 15 reviews

The Columbus Hotel | Four-poster Suite | 52-203

apartment, Middletown
Secluded Farmhouse, 30 Acres Private Estate. - Middletown, NY
9.4 117 reviews

Secluded Farmhouse, 30 Acres Private Estate.

apartment, Bloomingburg

Browse 5-Star Vacation Apartments in Middletown, NY

Staying in a luxury vacation apartment in Middletown, NY ensures every detail is considered, from high-end finishes to a prime location.

The Columbus Hotel | The Canopy Studio | 52-301 - Middletown, NY
8.0 10 reviews

The Columbus Hotel | The Canopy Studio | 52-301

apartment, Middletown

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.

Private Pool House On 8.5 Acre Estate - Middletown, NY
9.7 31 reviews

Private Pool House On 8.5 Acre Estate

apartment, Goshen
Creekside Farmhouse: Restored Farmhouse With Private Pond & Hot Tub - Middletown, NY
10 1 review

Creekside Farmhouse: Restored Farmhouse With Private Pond & Hot Tub

apartment, Unionville
Pool House On A Park-like Estate, Pet Friendly, 7 Min To Legoland. - Middletown, NY
No reviews

Pool House On A Park-like Estate, Pet Friendly, 7 Min To Legoland.

apartment, Goshen
Industrial Modern Home - 360 Views! - Middletown, NY
10 19 reviews

Industrial Modern Home - 360 Views!

apartment, Middletown

Top-Rated Apartments with a Pool in Middletown, NY

On-site pool access in Middletown, NY makes a proper swim in the heart of the city a wonderful part of your daily routine.

5bdrm Estate/tennis Near Legoland - Middletown, NY
9.9 66 reviews

5bdrm Estate/tennis Near Legoland

apartment, Scotchtown
Secluded Farmhouse, 30 Acres Private Estate. - Middletown, NY
9.4 117 reviews

Secluded Farmhouse, 30 Acres Private Estate.

apartment, Bloomingburg
Elegant Home W/7brs, Game Room, Luxury Yard, Pool - Middletown, NY
8.8 3 reviews

Elegant Home W/7brs, Game Room, Luxury Yard, Pool

apartment, Chester
Goshen Getaway: 5min To Legoland, 1hr To Nyc! - Middletown, NY
9.9 15 reviews

Goshen Getaway: 5min To Legoland, 1hr To Nyc!

apartment, Goshen

Our Favorite Apartments with a Hot Tub in Middletown, NY

Coming home to a hot tub after a day in Middletown, NY changes the whole feel of a stay; every vacation apartment here features one.

Industrial Modern Home - 360 Views! - Middletown, NY
10 19 reviews

Industrial Modern Home - 360 Views!

apartment, Middletown
Creekside Farmhouse: Restored Farmhouse With Private Pond & Hot Tub - Middletown, NY
10 1 review

Creekside Farmhouse: Restored Farmhouse With Private Pond & Hot Tub

apartment, Unionville
Custom Log Cabin, Hot Tub, Fire Pit & Wood Stove - Middletown, NY
10 1 review

Custom Log Cabin, Hot Tub, Fire Pit & Wood Stove

apartment, Florida
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