Compare Vacation Rentals & Airbnb in Middletown, NY

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Middletown, NY vacation rentals
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29 Rentals and Airbnb in Middletown, NY

Best family friendly Middletown, NY vacation rentals

Among the 29 accommodations in Middletown, NY, here are the 4 best family friendly rentals

Hudson Valley Horse Farm Stay | 10 Min To Legoland - Middletown, NY
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.
Victor-amazing Glamping Experience-middletown Ny - Middletown, NY
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.
Private Glamping Tent For 2 - Middletown, NY
9.5 11 reviews
Middletown, NY
22/07 – 26/07
$164/nighttotal: $656 (4 )

Private Glamping Tent For 2

1 2
glamping , Scotchtown
This glamping tent is located near Scotchtown, within easy reach of Legoland and local wineries. It has received excellent ratings for user experience, location, and cleanliness.
The tent sleeps up to three guests and features a full-size bed, twin-over-twin bunk beds, and a folding chair/bed. Enjoy a private outdoor area with seating, hammocks, a grill, and a picnic table, as well as access to a shared pool and discounted activities like a ropes course, paintball, and a camo run tube ride.
The Cathedral Barn - Middletown, NY
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).

Best Middletown, NY vacation rentals with parking

Cottage Suites - Middletown, NY
Middletown, NY
22/07 – 26/07
$204/nighttotal: $816 (4 )

Cottage Suites

1 2
cottage , Middletown
This self-catering cottage, part of the Cottage Suites in Middletown, offers a peaceful retreat within walking distance of the town centre.
The one-bathroom property sleeps two guests and includes a fridge, microwave, and free on-site parking; a refundable deposit of £195 is required.
Hike, Ski & Explore: Otisville Retreat W/ Yard! - Middletown, NY
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.
Pool, Fire Pit Bedroom & Alaska King Sleeps 16 - Middletown, NY
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.
Beautiful Log Cabin Style House - Middletown, NY
9.5 150 reviews
Middletown, NY
22/07 – 26/07
$611/nighttotal: $2444 (4 )

Beautiful Log Cabin Style House

1 2
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.

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?

    Want Peace Of Mind and Palace Near Woodbury Mall are the best vacation rentals with a pool in Middletown, NY.

  • What are the best restaurants with local dishes in Middletown, NY?

    For local fare, you can't go wrong with The Tavern at the Armory or The Olde Stone House. Both offer classic American dishes with a local twist.
  • What are the best rentals for families and kids 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?

    Beautiful Spacious House and Elegant Town Home Middletown Suburb Close To City are the best vacation rentals or Airbnb 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

Lakefront Cottage 10 Min To Legoland Farmstay - Middletown, NY
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).
Pool, Fire Pit Bedroom & Alaska King Sleeps 16 - Middletown, NY
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.

Best pet friendly Middletown, NY vacation rentals

Among the 29 accommodations in Middletown, NY, here are the 4 best pet friendly rentals

Waterlily-best Glamping Experience, Middletown Ny - 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.
Abomb! Adorable 2-bdrm Chalet With Lots Of Room! - Middletown, NY
9.8 6 reviews
Middletown, NY
21/08 – 23/08
$528/nighttotal: $1056 (2 )

Abomb! Adorable 2-bdrm Chalet With Lots Of Room!

2 5
chalet , Wurtsboro
This Wurtsboro holiday home is ideally situated within 5km of Mamakating Library, Veteran's Memorial Park, Sullivan County Parks & Recreation, Masten Lake, and the Mamakating Farmers Market.
Sleeping six guests in two bedrooms and one bathroom, this pet-friendly chalet boasts a fully equipped kitchen, air conditioning, a terrace, garden, spa, parking, and Wi-Fi, with barbecue facilities available on-site.
Nature Escape Studio - Sleeps 5 - Middletown, NY
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.
Hike, Ski & Explore: Otisville Retreat W/ Yard! - Middletown, NY
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.
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