Vacation rentals in Middletown, NY

29 available vacation rental offers

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Middletown, NY vacation rentals
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Best Vacation rentals and Airbnb offers in Middletown, NY

Compare Vacation Rentals for Families in Middletown, NY

These kid-friendly vacation rentals in Middletown, NY keep you close to top city attractions for a stress-free family vacation.

The Cathedral Barn - Middletown, NY
9.5 4 reviews
Middletown, NY
07/22 – 07/26
$640/nighttotal: $2560 (4 )

The Cathedral Barn

3 2
farm , Middletown
This Middletown, NY farm offers a 3-bedroom, 2-bathroom house sleeping up to 8 guests, perfect for family reunions or group getaways; age restrictions apply (40+ or under 40 with adult supervision).
The property includes a full kitchen with fridge, freezer, microwave, and dishwasher, air conditioning, a garden, fitness center, and parking, plus an adjoining farmhouse cottage available for larger groups or owner occupancy.
Glamping Tent- 10 Person Max Capacity - Middletown, NY
9.7 28 reviews
Middletown, NY
07/22 – 07/26
$217/nighttotal: $868 (4 )

Glamping Tent- 10 Person Max Capacity

1 2
glamping , Scotchtown
This glamping site is located within a private family campground and outdoor activity park in Scotchtown, a short drive from Middletown, NY, and approximately 10 miles from Legoland.
This family-friendly glamping tent accommodates up to 10 guests and offers a private outdoor area with seating, hammocks, a grill, and a fire pit, along with access to a shared swimming pool, with hot tub and sauna available for an additional fee.
Beautiful Log Cabin Style House - Middletown, NY
9.5 150 reviews
Middletown, NY
07/22 – 07/26
$437/nighttotal: $1748 (4 )

Beautiful Log Cabin Style House

1 2
apartment , Scotchtown
This log cabin-style apartment is located just minutes from Middletown, offering easy access to major shopping areas and restaurants. The apartment has received excellent ratings for location, cleanliness, and user experience. The apartment features three bedrooms and one bathroom, comfortably accommodating up to 12 guests. Amenities include a private sauna, a swimming pool, a fire pit, a large deck, and a variety of entertainment options like a video game, popcorn and slush machines, and access to discounted activities at the nearby Ring Homestead Adventure Camp.
Great Goshen Get-away Close To Legoland! - Middletown, NY
9.8 98 reviews
Middletown, NY
08/21 – 08/23
$370/nighttotal: $740 (2 )

Great Goshen Get-away Close To Legoland!

2 5
apartment , Goshen
This spacious apartment is ideally located in Goshen, just a short drive from Legoland New York, Woodbury Commons Shopping Outlets, and Bear Mountain State Park. It consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The apartment offers two separate units combined, providing four bedrooms, two kitchens, and two bathrooms, perfect for large families or groups. It includes a dedicated game room, modern amenities, and easy access to a variety of attractions, shopping, and outdoor activities.

Best Middletown, NY vacation rentals with parking

Pool, Fire Pit Bedroom & Alaska King Sleeps 16 - Middletown, NY
Middletown, NY
08/21 – 08/23
$1516/nighttotal: $3032 (2 )

Pool, Fire Pit Bedroom & Alaska King Sleeps 16

5 5
house , Chester
This Goshen villa, located 14 miles from Metro-North Harriman Station and 22 miles from Bear Mountain State Park, offers easy access to both commuter rail and outdoor recreation. This three-bathroom house sleeps 25 guests and boasts a private pool, jacuzzi, fully equipped kitchen, balcony, free Wi-Fi, and free parking.
Private Glamping Tent For 2 - Middletown, NY
9.5 11 reviews
Middletown, NY
07/22 – 07/26
$117/nighttotal: $468 (4 )

Private Glamping Tent For 2

1 2
glamping , Scotchtown
This glamping site in Scotchtown is conveniently located near Legoland and local wineries, offering excellent proximity to popular attractions.
This pet-friendly glamping experience accommodates up to two guests and features a private outdoor area with a grill, shared access to a pool, and discounted activities like ropes courses and paintball.
Hudson Valley Horse Farm Stay | 10 Min To Legoland - Middletown, NY
10 6 reviews
Middletown, NY
07/22 – 07/26
$418/nighttotal: $1672 (4 )

Hudson Valley Horse Farm Stay | 10 Min To Legoland

1 2
gîte , Scotchtown
This Scotchtown lakefront apartment offers a unique farmstay experience on a 7-acre property near Goshen's Heritage Trail and Harness Racing Museum, approximately two hours from Manhattan.
The one-bedroom, one-bathroom unit sleeps two guests and includes a fully equipped kitchen with a dishwasher, air conditioning, parking, canoe and paddleboat access, and on-site amenities such as a grill, firepit, and picnic tables.
Lakefront Cottage 10 Min To Legoland Farmstay - Middletown, NY
Middletown, NY
07/22 – 07/26
$633/nighttotal: $2532 (4 )

Lakefront Cottage 10 Min To Legoland Farmstay

1 2
cottage , Mechanicstown
This Hudson Valley lakefront cottage near Middletown, New York, is seven minutes from Goshen Village and an hour and fifteen minutes from New York City, offering easy access to LEGOLAND New York and local wineries.
The one-bedroom, one-bathroom guesthouse sleeps two, features a private dock, canoe, and paddleboat, a fenced courtyard, firepit, grill, and includes a pack 'n play and toddler bed upon request.

Frequently Asked Questions about vacation rentals in Middletown, NY

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

    The Middletown Thrall Park is a great place for families, with its playground, walking trails, and even a carousel. The Orange County Arboretum is also a great option, with its beautiful gardens and walking trails.
  • What are the best Airbnb and vacation rentals 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 during the shoulder seasons, like spring or fall. The weather is still nice, but the crowds are smaller and the prices are lower.
  • What are the most popular Airbnbs in Middletown, NY?

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

    The Wallkill Valley Rail Trail is a great way to get some exercise and enjoy the scenery, and it's free! The Middletown Thrall Park is also a great place to spend a day, with its playground, walking trails, and picnic areas.
  • 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?

    The 'The Brick House' is a great spot for local dishes, they have a fantastic menu with a focus on fresh, seasonal ingredients. 'The Gusto Restaurant' is also a great option, they offer a variety of Italian dishes.
  • What are the best rentals for families and kids in Middletown, NY?

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

    The Wallkill Valley Rail Trail is a great option for both walking and cycling, it's a paved trail that runs for miles along the Wallkill River. The Orange County Arboretum also has a number of walking trails.
  • 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 Wallkill Valley Rail Trail is pet-friendly, so you can bring your furry friend along for a walk or bike ride. The Thrall Park also has a dog park.
  • What are the benefits of choosing a vacation rental in Middletown, NY?

    Vacation rentals offer more space and privacy than a hotel. They can also be a more affordable option, especially if you're traveling with a group.
  • What are the top sports attractions and facilities in Middletown, NY?

    Middletown has a few sports facilities, including the Middletown High School Athletic Complex, which has a football field, track, and baseball field. There's also the Middletown YMCA, which offers a variety of fitness classes and activities.

Destinations nearby

Choose the Right Vacation Rentals with a Terrace in Middletown, NY

Enjoy your own private terrace with city skyline views at these vacation rentals in Middletown, NY.

Pool, Fire Pit Bedroom & Alaska King Sleeps 16 - Middletown, NY
Middletown, NY
08/21 – 08/23
$1516/nighttotal: $3032 (2 )

Pool, Fire Pit Bedroom & Alaska King Sleeps 16

5 5
house , Chester
This Goshen villa, located 14 miles from Metro-North Harriman Station and 22 miles from Bear Mountain State Park, offers easy access to both commuter rail and outdoor recreation. This three-bathroom house sleeps 25 guests and boasts a private pool, jacuzzi, fully equipped kitchen, balcony, free Wi-Fi, and free parking.
Lakefront Cottage 10 Min To Legoland Farmstay - Middletown, NY
Middletown, NY
07/22 – 07/26
$633/nighttotal: $2532 (4 )

Lakefront Cottage 10 Min To Legoland Farmstay

1 2
cottage , Mechanicstown
This Hudson Valley lakefront cottage near Middletown, New York, is seven minutes from Goshen Village and an hour and fifteen minutes from New York City, offering easy access to LEGOLAND New York and local wineries.
The one-bedroom, one-bathroom guesthouse sleeps two, features a private dock, canoe, and paddleboat, a fenced courtyard, firepit, grill, and includes a pack 'n play and toddler bed upon request.

Discover Pet-Friendly Vacation Rentals in Middletown, NY

Travel with ease to Middletown, NY with pet-friendly rentals located near local dog parks and scenic city walks.

Hike, Ski & Explore: Otisville Retreat W/ Yard! - Middletown, NY
8.0 2 reviews
Middletown, NY
08/21 – 08/23
$522/nighttotal: $1044 (2 )

Hike, Ski & Explore: Otisville Retreat W/ Yard!

4 5
apartment , Otisville
This spacious 193 m² vacation home in Mount Hope is situated a 14-minute walk from Otisville Veterans Memorial Park and a 2-minute drive from Mount Hope Town Park.
This family-friendly apartment offers four bedrooms, three bathrooms, a fully equipped kitchen, air conditioning, a fireplace, a private garden with a fire pit and barbecue, and in-unit laundry.
Family Getaway Near Hudson Valley Attractions - Middletown, NY
Middletown, NY
08/21 – 08/23
$655/nighttotal: $1310 (2 )

Family Getaway Near Hudson Valley Attractions

1 5
apartment , Mechanicstown
This Mechanicstown rental unit offers a peaceful retreat in a quiet neighborhood, providing convenient access to Hudson Valley attractions.
This 3-bedroom, 1-bathroom apartment accommodates up to 4 guests and features a fully equipped kitchen, air conditioning, complimentary parking, and easy self-check-in for a comfortable stay.
House Near Legoland, Farms, And Airport/ Train - Middletown, NY
Middletown, NY
07/22 – 07/26
$433/nighttotal: $1732 (4 )

House Near Legoland, Farms, And Airport/ Train

3 2
apartment , Scotchtown
This 3-bedroom, 1-bathroom rental unit is located in Scotchtown, offering proximity to Legoland and convenient access to Hudson Valley attractions, including a Metro-North station and Stewart Airport.
This pet-friendly apartment accommodates up to 4 guests and features a full kitchen, air conditioning, and parking, with opportunities for fruit picking and hiking nearby.
Nature Escape Studio - Sleeps 5 - Middletown, NY
10 4 reviews
Middletown, NY
07/22 – 07/26
$272/nighttotal: $1088 (4 )

Nature Escape Studio - Sleeps 5

1 2
cabin , Scotchtown
This pet-friendly cabin rental, part of the Ring Homestead Adventure Camp near Middletown, NY, offers easy access to Scotchtown attractions.
The one-bedroom, one-bathroom cottage features an open-plan design with a queen bed and bunk bed, sleeping up to five guests, and includes a kitchen, propane grill, fire pit, and summer pool access; hot tub and sauna rentals are available.
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