Find short term rentals in Middletown, NY at the best prices
23 available short term rental offers
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Best Short term and Weekly rentals in Middletown, NY
9.5 110 reviews
Middletown, NY
22/07 – 26/07
$241/nighttotal: $964 (4 )
Groovy Digs For A Unique Stay On Murray Hill
1 2
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.
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).
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.
10 2 reviews
Middletown, NY
21/08 – 23/08
$770/nighttotal: $1540 (2 )
Parkway House Goshen Bed & Breakfast Suite #4
1 5
B&B , Goshen
This Victorian Inn is located in the village centre of Goshen, 4 kilometres from Legoland New York, 15 kilometres from Woodbury Commons Premium Shopping Outlets, and offers views of the Goshen Historic Track. This family-friendly guesthouse provides a spacious 2-bedroom suite with a capacity for six guests, featuring air conditioning and Wi-Fi, with complimentary breakfast served daily.
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.
Middletown, NY
21/08 – 23/08
$770/nighttotal: $1540 (2 )
Parkway House Goshen Bed & Breakfast Suite #1
1 5
B&B , Goshen
This Bed and Breakfast is located in Goshen's city centre, a 4-minute drive from Legoland New York and near the Goshen Harness Racing Track. This 900 square meter guesthouse offers one bedroom and one bathroom, accommodating up to six guests, with features including air conditioning, internet, a terrace, and a garden, and is ideal for those seeking a base for visiting local attractions such as the United States Military Academy and the Harness Racing Museum and Hall of Fame.
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.
Middletown, NY
22/07 – 26/07
$237/nighttotal: $948 (4 )
Comfortable Bedroom Close To Legoland And Hiking
1 2
apartment , Scotchtown
This one-bedroom flat in Scotchtown is conveniently located 22.5 kilometres from Legoland and Soons Orchard, with easy access to local shops and restaurants. This apartment offers a king-size bed, shared kitchen and living room, and accommodates up to two guests, with parking and air conditioning available.
10 1 review
Middletown, NY
22/07 – 26/07
$250/nighttotal: $1000 (4 )
Charming Bedroom Close To Legoland & Shopping
1 2
apartment , Mechanicstown
This Mechanicstown flat is situated just 1.6 kilometres from Legoland and 160 metres from local shops, offering a convenient base for exploring the Hudson Valley. This one-bedroom flat accommodates two guests and features a Queen-size bed, air conditioning, internet, a kitchen, and free parking, with shared access to a living room for added comfort.
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
22/07 – 26/07
$245/nighttotal: $980 (4 )
Columbus 402
1 2
apartment , Middletown
This one-bedroom flat is centrally located in Middletown, offering easy access to local attractions and transport links. This accommodation provides space for two guests, featuring a kitchen, air conditioning, and internet, making it a practical base for exploring the area.
9.4 41 reviews
Middletown, NY
22/07 – 26/07
$179/nighttotal: $716 (4 )
Cozy, Dainty & Meticulously Clean Home
2 2
house , Scotchtown
This charming bed and breakfast is conveniently located in Scotchtown, just a short drive from attractions like Legoland, the Catskills Resorts World Casino, and Kartrite Resort. It has consistently received excellent ratings for its cleanliness, location, and overall guest experience. The property features two bedrooms and one bathroom, comfortably accommodating up to six guests. Guests can enjoy a private yard with a patio, a pool, and various other amenities, making it ideal for families or groups seeking a relaxing and enjoyable stay.
Best family friendly Middletown, NY Short term rentals
Among the 23 accommodations in Middletown, NY, here are the 4 best family friendly rentals
Middletown, NY
21/08 – 23/08
$868/nighttotal: $1736 (2 )
Parkway House Goshen Bed & Breakfast Suite #2
1 5
B&B , Goshen
This restored Victorian inn is located in the centre of Goshen Village, just a 4-minute drive from Legoland New York Theme Park, and offers a 2-bedroom suite with exclusive views of the Goshen Historic Track. The 800 square meter property provides accommodation for up to 8 guests, featuring air conditioning, Wi-Fi, a terrace, and a garden, with options to rent the entire house, barn, or the whole property, and serving a complimentary gourmet breakfast daily.
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.
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.
9.8 98 reviews
Middletown, NY
22/07 – 26/07
$330/nighttotal: $1320 (4 )
Great Goshen Get-away Close To Legoland!
2 2
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.
Best Middletown, NY lodging with a kitchen
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.
10 5 reviews
Middletown, NY
22/07 – 26/07
$245/nighttotal: $980 (4 )
Cozy Downtown Studio W/ Kitchen & Workspace
1 2
apartment , Middletown
This studio flat is centrally located in Middletown's downtown district, offering immediate access to dining, cafes, and breweries, and is conveniently situated 700 meters from Touro College and Garnet Health Medical Center. This accommodation offers a fully equipped kitchen with a fridge, freezer, and microwave, air conditioning, a garden, parking, one bathroom, and capacity for two guests, with self-check-in via a smart lock and access to a shared 24/7 laundry facility.
10 4 reviews
Middletown, NY
22/07 – 26/07
$379/nighttotal: $1516 (4 )
Nature Escape Studio - Sleeps 5
1 2
cabin , Scotchtown
This pet-friendly tiny home, part of the Ring Homestead Adventure Camp near Middletown, New York, is situated approximately 16 km from Scotchtown, offering easy access to local amenities and attractions. Sleeping up to five guests, this self-catering lodge boasts a queen bed, bunk beds, an open-plan living area, on-site propane grill, fire pit, picnic table, and optional hot tub and sauna rental; plus seasonal pool access and nearby access to ropes courses, paintball, and tubing.
Middletown, NY
22/07 – 26/07
$688/nighttotal: $2752 (4 )
Family Getaway Near Hudson Valley Attractions
1 2
apartment , Mechanicstown
This three-bedroom flat in Mechanicstown offers a peaceful setting within a quiet neighbourhood, just a short distance from Hudson Valley attractions. This self-contained property accommodates up to four guests, featuring a fully equipped kitchen, air conditioning, internet, and complimentary parking, with pet-friendly arrangements.
Frequently Asked Questions about short term rentals in Middletown, NY
What are the best short term rentals in Middletown, NY?
Best Middletown, NY lodging with laundry available
9.3 3 reviews
Middletown, NY
22/07 – 26/07
$245/nighttotal: $980 (4 )
The Columbus Hotel | The Canopy Studio | 52-301
1 2
apartment , Middletown
This central Middletown flat is located in the downtown district, offering easy walking access to the Middlesex County Historical Society, just 500 meters away, and close to shops and restaurants. This one-bedroom flat accommodates two guests and includes internet, a kitchen, and air conditioning, making it a practical base for exploring Middletown's historical sites.
9.7 23 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.
Best Middletown, NY lodging with air conditioning
10 187 reviews
Middletown, NY
22/07 – 26/07
$319/nighttotal: $1276 (4 )
Stone Oak Tree Farm Canaan Fir Room
1 2
apartment , Middletown
Stone Oak Christmas Tree Farm B&B is located near Middletown, Orange County, New York, a short drive from the Shawangunk Ridge and the Hudson River, offering a peaceful woodland setting. This charming property has received excellent ratings for its cleanliness, location, and user experience. The B&B is housed in a beautiful timber-framed barn, designed to evoke the Christmas spirit year-round, and can accommodate up to two guests. It features a well-equipped kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a garden, and parking.