Vacation Rentals in Middletown, NY

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

View Top Kid-Friendly Holiday Rentals in Middletown, NY

Keep the whole group together under one roof with plenty of space to lounge at family holiday rentals in Middletown, NY.

Beautiful Log Cabin Style House - Middletown, NY
9.5 157 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.
Farmhouse Living And Relaxation! Summer Rental - Middletown, NY
No reviews

Farmhouse Living And Relaxation! Summer Rental

apartment, Chester
This country estate offers a secluded rural retreat on 125 acres, located near Chester, providing a peaceful escape with opportunities to explore scenic farmland and interact with farm animals.
This 3-bedroom, 3-bathroom apartment accommodates up to 6 guests and features a private swimming pool, extensive grounds, and a serene environment with breathtaking sunset views.
12 Person Glamping Tent- Rte 66 - Middletown, NY
9.5 23 reviews

12 Person Glamping Tent- Rte 66

glamping, Scotchtown
This glamping shelter is situated just a short distance from Middletown, offering easy access to shopping, dining, and attractions like Legoland and local wineries. It has received excellent ratings for location, cleanliness, and user experience.
The tent features a full-size bed, twin bunk beds, and a folding chair/bed, comfortably accommodating up to 15 guests. The property also includes a shared pool, a private outdoor area with seating, hammocks, a grill, and a picnic table, as well as discounted access to adventure activities such as a ropes course, paintball, and a camo run tube ride.
Glamping Tent- 11 Person Max Cap. - Middletown, NY
8.7 3 reviews

Glamping Tent- 11 Person Max Cap.

glamping, Scotchtown
This glamping shelter is situated just minutes from Middletown, offering easy access to shopping, dining, and attractions like Legoland and local wineries. The surrounding area is quiet and private, perfect for a relaxing getaway.
The Fionna - Amazing Glamping tent can accommodate up to nine guests and features a bedroom and bathroom. Guests can enjoy a range of amenities, including a private outdoor area with a grill, fire pit, and hammock, as well as access to a shared pool and discounted rates at a nearby paintball shop.

Best Middletown, NY holiday rentals with parking

The Columbus Hotel | The Wayfarer Suite | 52-406 - Middletown, NY
9.4 23 reviews

The Columbus Hotel | The Wayfarer Suite | 52-406

apartment, Middletown
This private mini studio in downtown Middletown, NY, is located directly above a restaurant and bar, offering convenient access to local amenities.
This self-contained apartment for one guest includes air conditioning, Wi-Fi, a workspace, a full-size bed, a kitchen with a fridge, freezer, and microwave, a private bathroom with a stand-up shower, and complimentary on-premises parking.
9 Person Glamping Tent- Aurora - Middletown, NY
10 2 reviews

9 Person Glamping Tent- Aurora

glamping, Scotchtown
This glamping shelter is situated just a short drive from Middletown, offering easy access to shopping, dining, and attractions like Legoland and local wineries. The site has received excellent ratings for its location, cleanliness, and overall experience.
The accommodation can sleep up to nine guests and comes with a double bed and additional bedding, as well as a private bathroom. Guests can enjoy a range of amenities including a swimming pool, a Jacuzzi, a fire pit, a picnic table, and a hammock, as well as solar electricity.
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space - Middletown, NY
10 35 reviews

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

apartment, Chester
This spacious house is located in a peaceful rural setting near Goshen, just a short drive from popular attractions like LEGOLAND® New York and Castle Fun Center, making it a great base for exploring the area. The house has received excellent reviews from previous guests, highlighting its comfortable and convenient amenities.
The property has five bedrooms and three bathrooms, comfortably accommodating up to ten guests. Enjoy a dip in the private pool, relax in the hot tub, or cook up a meal on the barbecue, all while taking in the tranquil surroundings.
The Columbus Hotel | The Upper Studio | 52-402 - Middletown, NY
8.0 5 reviews

The Columbus Hotel | The Upper Studio | 52-402

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.

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.

Popular destinations

Find Holiday Rentals with Balconies in Middletown, NY

Catch the morning breeze and watch the local world go by from holiday rentals featuring an outdoor balcony in Middletown, NY.

 - Middletown, NY
No reviews

studio, Middletown
This studio apartment is located in a well-connected district of Middletown, offering convenient access to local landmarks and transportation routes.
This 20 square meter self-contained unit accommodates one guest and features a fridge, microwave oven, air conditioning, and a terrace, with a strict policy against parties to ensure a peaceful stay.
 - Middletown, NY
No reviews

apartment, Middletown
This flat is located in a central Middletown district, offering convenient access to local attractions and amenities, with key landmarks within easy reach.
This 23 square meter studio apartment accommodates up to three guests and features air conditioning, a kitchen with a fridge and microwave, and a balcony, with Wi-Fi provided for your convenience.
Pool, Fire Pit Bedroom & Alaska King Sleeps 16 - Middletown, NY
No reviews

Pool, Fire Pit Bedroom & Alaska King Sleeps 16

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.
Spectacular Historic Mansion W/pool&tennis - Middletown, NY
10 20 reviews

Spectacular Historic Mansion W/pool&tennis

apartment, Chester
This ten-bedroom luxury holiday home, perfect for large groups, is situated near Goshen, New York, approximately 4.8 kilometres from LEGOLAND® New York and other attractions.
Offering a private pool, jacuzzi, tennis court, and ample amenities including a fully equipped kitchen and free Wi-Fi, this spacious property comfortably accommodates up to 26 guests.

Find Dog-Friendly Holiday Rentals in Middletown, NY

Give your four-legged companion a cozy place to curl up at pet-friendly holiday rentals in Middletown, NY.

9 Person Glamping Tent And Site- Autumn - Middletown, NY
9.3 3 reviews

9 Person Glamping Tent And Site- Autumn

glamping, Scotchtown
This glamping shelter is located just a short drive from Middletown, offering easy access to shopping, restaurants, and attractions like Legoland and local wineries. The property enjoys excellent ratings for user experience, location, and cleanliness.
The tent sleeps up to 9 guests and comes with basic linen, a fire pit, a grill, and a picnic table. You can also enjoy the on-site swimming pool, jacuzzi, and a range of additional activities and amenities.
The Cozy Goshen Home, 5mins From Legoland And Near Skiing! - Middletown, NY
10 23 reviews

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

apartment, Goshen
This Goshen, New York holiday home is situated approximately 5 kilometres from Goshen Historic Track and the Orange County Genealogical Society, and within 10 kilometres of LEGOLAND® New York and the Harness Racing Museum & Hall of Fame.
This smoke-free, family-friendly property sleeps ten guests in four bedrooms and two bathrooms, offering a fully equipped kitchen, air conditioning, parking, Wi-Fi, and barbecue facilities.
9 Person Glamping Tent- Chipmunk - Middletown, NY
9.6 16 reviews

9 Person Glamping Tent- Chipmunk

glamping, Scotchtown
Chipmunk Cove#26 is situated in Scotchtown, just a short distance from Legoland and other attractions. This accommodation receives excellent ratings for location, cleanliness, and user experience.
The tent offers a spacious layout, accommodating up to 45 guests, making it perfect for large groups. Amenities include picnic tables, BBQ grills, a fridge, and a bonfire pit, alongside access to Adventureland for additional entertainment.
9 Person- Glamping Tent Site- Aphrodite - Middletown, NY
10 3 reviews

9 Person- Glamping Tent Site- Aphrodite

glamping, Scotchtown
The Aphrodite Goddess Of Love glamping shelter is situated just a short drive from Middletown, offering easy access to Legoland and local wineries. This accommodation has received excellent ratings for location, cleanliness, and overall user experience.
This one-bedroom, one-bathroom glamping shelter can comfortably accommodate up to nine guests. Enjoy a unique glamping experience with amenities like solar electricity, a grill, a fire pit, a picnic table, a hammock, and a private pool.
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