Best apartment offers in Middletown, NY

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Middletown, NY apartments
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46 Best apartments in Middletown, NY

Guest-Favourite Holiday Apartments for Families in Middletown, NY

Selecting the perfect family holiday apartment in Middletown, NY makes all the difference, especially when city attractions are within easy reach for a stress-free trip.

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

Secluded Farmhouse, 30 Acres Private Estate.

apartment, Bloomingburg
This six-bedroom property is located in a secluded area near Bloomingburg, New York, just a short drive from the Shawangunk Wine Trail, Minnewaska State Park, and the Storm King Art Center. The apartment has received excellent ratings for user experience, location, and cleanliness.
This spacious house can accommodate up to 16 guests and features a fully equipped kitchen, a swimming pool, a tennis court, and a garden. Guests can enjoy a variety of activities, including swimming, tennis, hiking, and exploring the nearby attractions.
Spacious 6br Villa - Serene Scenic Mountain Escape - Middletown, NY
9.4 10 reviews

Spacious 6br Villa - Serene Scenic Mountain Escape

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

5bdrm Estate/tennis Near Legoland

apartment, Scotchtown
This 1917 farmhouse, renovated by superhosts Susan and Charlie, is located in the Hudson Valley, a short drive from Scotchtown, and within 20 minutes of Woodbury Commons, LegoLand, and Angry Orch. The property has received excellent ratings for location, cleanliness, and overall experience.
The farmhouse offers five bedrooms and two bathrooms, comfortably accommodating up to 12 guests. Enjoy a tranquil setting with multiple living areas, a heated pool, a tennis court, a fire pit, and various patios, along with complimentary amenities, on-site yoga and massage services, and easy access to local attractions.
Serene Rustic Retreat With Lake - Middletown, NY
10 8 reviews

Serene Rustic Retreat With Lake

apartment, Otisville
This lakeside lodge is situated near Otisville, New York, within 5 kilometres of Gobbler's Knob State Forest, Otisville Veterans Memorial Park, and Delaware and Hudson Canal County Park.
Sleeping six guests, this four-bedroom, three-bathroom property boasts a fully equipped kitchen, a fireplace, terrace, and garden; enjoy nearby water activities and the convenience of internet access.

Best Middletown, NY holiday apartments with a kitchen

The Columbus Hotel | The Galley Studio | 89-203 - Middletown, NY
9.3 3 reviews

The Columbus Hotel | The Galley Studio | 89-203

apartment, Middletown
This centrally located flat offers a stylish and modern base in Middletown's prime district, providing convenient access to key landmarks and attractions such as the Middletown Museum (500m) and the historic Middletown Abbey (1.2km).
This one-bedroom apartment accommodates two guests and features air conditioning, a kitchen with a fridge, freezer, and microwave, and a garden, making it ideal for travellers seeking a comfortable stay with easy access to local amenities.
Adorable Three Bedroom Irish Cape Home. - Middletown, NY
9.9 22 reviews

Adorable Three Bedroom Irish Cape Home.

apartment, Middletown
This three-bedroom house in Middletown, Hudson Valley, is situated approximately 113km from New York City and offers easy access to highways 17 and 84.
The property sleeps six guests across three bedrooms and two bathrooms, boasting a fully equipped kitchen, a private garden with a fire pit, and a dry infrared sauna; nearby attractions include various Hudson Valley sights.
Lake Trail Retreat - Middletown, NY
9.5 26 reviews

Lake Trail Retreat

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.
Cozy Delight - Middletown, NY
9.3 26 reviews

Cozy Delight

apartment, Scotchtown
This Scotchtown holiday home is situated near Middletown, New York, approximately 10-15 km from Middletown's shopping mall and major hospital.
The three-bedroom property, sleeping four, boasts a kitchen with fridge, freezer, and microwave, air conditioning, a garden, parking, and internet access; enjoying gorgeous sunset views.

Frequently asked questions about apartment rentals in Middletown, NY

  • What are the top cultural and historical sites in Middletown, NY?

    Middletown has a lot of history. You can visit the historic Paramount Theatre, the Orange County Historical Society Museum, and the Thrall Park Victorian Mansion. For art, you can visit the Orange County Arts Center, which has a variety of exhibits and events.
  • What are the best apartments in Middletown, NY?

  • What makes Middletown, NY unique or famous?

    Middletown is known for its rich history, its beautiful natural surroundings, and its vibrant arts and culture scene. The city is also home to a number of historic buildings, including the historic Paramount Theatre and the Thrall Park Victorian Mansion.
  • 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?

    Middletown has a few great local markets, like the Middletown Farmers Market on Saturdays. You can also find some great street food vendors at the annual Middletown Street Fair, which is held in the summer.
  • 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 called the Orange County Transit, which can get you around the city and to nearby towns. The system is pretty reliable, but it's not as extensive as in larger 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?

    Middletown has a variety of seasonal events and festivals throughout the year, including the annual Middletown Street Fair in the summer, the Middletown Winter Festival in December, and the annual Middletown Irish Festival in March.
  • What are the best pet friendly apartments in Middletown, NY?

  • What amenities are typically included in apartments in Middletown, NY?

    Most apartments in Middletown will include basic amenities like central heating and air conditioning, a refrigerator, a stove, and a dishwasher. Some apartments may also include a washer and dryer, a balcony, or a parking space.
  • What are the best apartments with parking in Middletown, NY?

  • What leisure activities are available for relaxation in Middletown, NY?

    Middletown has a lot of options for relaxation. You can take a walk or bike ride along the Wallkill River, visit the beautiful Thrall Park, or go for a swim at the Middletown YMCA.

Popular destinations

Best Middletown, NY holiday apartments with air conditioning

Craftsman Hideaway At The 1841 Farmhouse - Middletown, NY
No reviews

Craftsman Hideaway At The 1841 Farmhouse

apartment, Walton Park
Book this Holiday rental. Your accommodation will be based in Walton Park.
Facilities and services: free parking and a kitchen. Take advantage of the air conditioning in this apartment!
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 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.
The Columbus Hotel | The Residence Studio | 89-206 - Middletown, NY
10 2 reviews

The Columbus Hotel | The Residence Studio | 89-206

apartment, Middletown
This studio flat is situated in downtown Middletown, placing you within easy walking distance of Touro University, Garnet Health, and the Paramount Theatre, with dining options readily accessible.
This accommodation offers a cook-ready kitchenette with stainless steel appliances, a dedicated workstation, free high-speed Wi-Fi, and smart-lock check-in, ideal for weekly and monthly stays with on-site parking and shared laundry facilities.
Groovy Digs For A Unique Stay On Murray Hill - Middletown, NY
9.5 112 reviews

Groovy Digs For A Unique Stay On Murray Hill

apartment, Goshen
This unique apartment is located in a peaceful residential area of Goshen, just a short walk from the lively downtown area and close to the Goshen Theater and the Elkhart County 4-H Fairgrounds. It has consistently received excellent ratings for user experience, location, and cleanliness.
The apartment features a fully equipped kitchen and a spacious living area with a Murphy bed, perfect for accommodating two guests. Enjoy a private bar, pinball machines, a relaxing patio, a walk-in shower, and the company of a friendly chihuahua.

Check Out Pet-Friendly Holiday Apartments in Middletown, NY

Discover our selection of pet-friendly holiday apartments in Middletown, NY, each specifically chosen to make your visit truly memorable.

Beautiful Log Cabin Style House - Middletown, NY
9.5 153 reviews

Beautiful Log Cabin Style House

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.
Private Home With Pool & Jacuzzi In The Hudson Valley - Middletown, NY
10 9 reviews

Private Home With Pool & Jacuzzi In The Hudson Valley

apartment, Montgomery
This detached house in Montgomery offers a secluded Hudson Valley retreat, approximately 32 kilometres from Beacon, Newburgh, and LEGOLAND.
This pet-friendly property boasts over 185 square metres of living space, featuring 3 bedrooms, a home office, 2.5 bathrooms, a Jacuzzi, a seasonal swimming pool, and a fire pit, with nearby access to wineries, hiking trails in the Catskill Mountains and Shawangunk Ridge, and the Hudson River for kayaking and fishing.
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 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.
Cozy Apartment Near Legoland! - Middletown, NY
8.9 7 reviews

Cozy Apartment Near Legoland!

apartment, Middletown
This one-bedroom apartment, situated in New Hampton, approximately 32 kilometres from Middletown, offers easy access to Legoland New York and other Hudson Valley attractions.
The 770-square-metre property boasts a spacious layout with a separate living room, fully equipped kitchen, terrace, parking, and sleeps up to nine guests, featuring free Wi-Fi.
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