Vacation Rentals in Middletown, NY

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Middletown, NY holiday rentals
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29 Holiday rentals and Airbnb in Middletown, NY

Best family friendly Middletown, NY holiday rentals

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

Victor-amazing Glamping Experience-middletown Ny - Middletown, NY
9.7 64 reviews
Middletown, NY
22/07 – 26/07
A$195/nighttotal: A$780 (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.
2 Unit Condo Minutes From Lego Land - Middletown, NY
9.8 98 reviews
Middletown, NY
22/07 – 26/07
A$336/nighttotal: A$1344 (4 )

2 Unit Condo Minutes From Lego Land

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.
The Cathedral Barn - Middletown, NY
9.5 4 reviews
Middletown, NY
22/07 – 26/07
A$910/nighttotal: A$3640 (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).
Hike, Ski & Explore: Otisville Retreat W/ Yard! - Middletown, NY
8.0 2 reviews
Middletown, NY
21/08 – 23/08
A$743/nighttotal: A$1486 (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.

Best Middletown, NY holiday rentals with parking

Elegant Town Home Middletown Suburb Close To City - Middletown, NY
Middletown, NY
27/06 – 04/07
A$731/nighttotal: A$5117 (7 )

Elegant Town Home Middletown Suburb Close To City

3 2
apartment , Washington Heights
This modern house is situated in Middletown, New York, just a short drive from Washington Heights and its attractions. The surrounding area offers a peaceful change of pace, with vineyards, breweries, and historical sites close by.
This three-bedroom, three-bathroom property provides spacious and comfortable accommodation for your stay. The house is fully equipped with modern amenities, including air conditioning, a Jacuzzi, and parking, as well as travel brochures to help you explore the local area.
Abomb! Adorable 2-bdrm Chalet With Lots Of Room! - Middletown, NY
9.8 6 reviews
Middletown, NY
21/08 – 23/08
A$537/nighttotal: A$1074 (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.
Lakefront Cottage 10 Min To Legoland Farmstay - Middletown, NY
Middletown, NY
27/06 – 04/07
A$764/nighttotal: A$5348 (7 )

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).
Huge Retreat W Alaska King, Pool & Jacuzzi Tub Indoor - Middletown, NY
Middletown, NY
21/08 – 23/08
A$2157/nighttotal: A$4314 (2 )

Huge Retreat W Alaska King, Pool & Jacuzzi Tub Indoor

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.

Frequently asked questions about holiday rentals in Middletown, NY

  • Which neighborhood in Middletown, NY should you consider for a vacation rental?

    The area around the historic downtown is a good option for a vacation rental, as it's close to shops, restaurants, and the Paramount Theatre. You could also try the neighbourhood around the Thrall Park, which is quieter and has a more residential feel.
  • What are the best Airbnb and holiday rentals in Middletown, NY?

  • What are the top family-friendly attractions in Middletown, NY?

    For families, the Thrall Park is a great option with its lake, playground, and walking trails. You might also enjoy the Orange County Historical Society Museum, which has exhibits about the local history and culture.
  • What are the most popular Airbnbs in Middletown, NY?

  • When is the best time to book a vacation rental in Middletown, NY?

    The best time to book a vacation rental in Middletown is probably in the spring or autumn, when the weather is pleasant and there are fewer crowds. If you're looking for a more affordable option, you could try booking during the off-season, but keep in mind that some attractions might be closed.
  • What are the best holiday rentals with a pool in Middletown, NY?

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

  • What are the best budget-friendly activities in Middletown, NY?

    A walk around the downtown area, exploring the shops and restaurants, is a great way to spend an afternoon. You could also visit the Thrall Park, which is free to enter and has plenty of walking trails and a playground.
  • What are the best rentals for families and kids in Middletown, NY?

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

    For local dishes, you could try the 'The Black Cat' or 'The Cornerstone' - both offer classic American comfort food with a modern twist. There's also 'The Middletown Diner' which is a great place for a classic breakfast or lunch.
  • 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 holiday rentals or Airbnb with a jacuzzi in Middletown, NY.

  • What are the best walking or cycling routes in Middletown, NY?

    The Wallkill Valley Rail Trail is a popular walking and cycling route that runs through Middletown. It's a paved trail that's mostly flat, making it suitable for all levels of fitness. There's also the scenic route along the banks of the Wallkill River, which offers beautiful views of the surrounding countryside.
  • Are there pet-friendly attractions in Middletown, NY?

    Yes, Thrall Park is pet-friendly and has a designated dog park. Many restaurants also have outdoor seating areas that welcome dogs.
  • What are the benefits of choosing a vacation rental in Middletown, NY?

    Vacation rentals offer more space and privacy than hotels, and are often more affordable, especially for larger groups. You can also enjoy the convenience of having a kitchen and laundry facilities.

Destinations nearby

Best Middletown, NY holiday rentals with a balcony

Huge Retreat W Alaska King, Pool & Jacuzzi Tub Indoor - Middletown, NY
Middletown, NY
21/08 – 23/08
A$2157/nighttotal: A$4314 (2 )

Huge Retreat W Alaska King, Pool & Jacuzzi Tub Indoor

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.
Lakefront Cottage 10 Min To Legoland Farmstay - Middletown, NY
Middletown, NY
27/06 – 04/07
A$764/nighttotal: A$5348 (7 )

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).

Best pet friendly Middletown, NY holiday rentals

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

Beautiful Log Cabin Style House - Middletown, NY
9.5 150 reviews
Middletown, NY
21/08 – 23/08
A$570/nighttotal: A$1140 (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.
Nature Escape Studio - Sleeps 5 - Middletown, NY
10 4 reviews
Middletown, NY
22/07 – 26/07
A$386/nighttotal: A$1544 (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.
Family Getaway Near Hudson Valley Attractions - Middletown, NY
Middletown, NY
21/08 – 23/08
A$932/nighttotal: A$1864 (2 )

Family Getaway Near Hudson Valley Attractions

1 5
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.
9 Person Glamping Tent- Dreamweaver - Middletown, NY
10 6 reviews
Middletown, NY
22/07 – 26/07
A$161/nighttotal: A$644 (4 )

9 Person Glamping Tent- Dreamweaver

1 2
glamping , Scotchtown
This 9-person glamping tent, the 'Dreamweaver', is located in a quiet, private setting near Scotchtown, a few minutes' drive from Middletown, offering easy access to Legoland and local wineries.
The self-catering dwelling boasts a bedroom, bathroom, solar electricity, on-site grill, fire pit, hammock, shared pool access, and discounted entry to a ropes course, camo run tube ride, and paintball activities, accommodating up to nine guests and welcoming pets for an additional fee.
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