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Middletown, NY villas
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12 Villa rentals in Middletown, NY

Top-Rated Vacation Homes near the City Center in Middletown, NY

Stay close to the action with central vacation homes in Middletown, NY, keeping downtown landmarks within easy walking distance.

Hudson Valley Horse Farm Stay | 10 Min To Legoland - Middletown, NY
10 12 reviews

Hudson Valley Horse Farm Stay | 10 Min To Legoland

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.
Hello Small Stone - Middletown, NY
9.6 5 reviews

Hello Small Stone

cottage, Otisville
This charming cottage is located just a short drive from Otisville, offering a peaceful retreat near the stunning natural beauty of Minnewaska State Park and Sam's Point Preserve. The surrounding area is quiet and secluded, perfect for a relaxing getaway.
The two-bedroom cottage comfortably accommodates four guests. It features a fully equipped kitchen, a spacious living room with a Smart TV, and a private backyard with a pond and a porch perfect for grilling.
Cozy Tiny House Retreat For Two - Middletown, NY
8.9 28 reviews

Cozy Tiny House Retreat For Two

house, Middletown
This romantic apartment in Middletown is located in a quiet area, offering a private escape with convenient access to local attractions.
This 1-bedroom, 1-bathroom unit accommodates two guests and features a private jacuzzi, a microwave, a fridge, air conditioning, and parking, making it ideal for couples seeking a peaceful getaway.
Welcome To The Farmhouse At The Barn! - Middletown, NY
9.3 3 reviews

Welcome To The Farmhouse At The Barn!

gîte, Scotchtown
This charming farmhouse, located in the beautiful Hudson Valley, is a short drive from attractions like Legoland and the Renaissance Faire. Guests consistently rate this home excellent for its location, cleanliness, and overall experience.
This spacious vacation rental, ideal for large groups, comfortably accommodates up to 16 guests in 8 bedrooms and 4 bathrooms. The home features modern amenities, a large garden, and parking, making it the perfect place to relax and enjoy the Hudson Valley.

Best family friendly Middletown, NY villas and beach houses

Among the 4 accommodations in Middletown, NY, here are the 4 best family friendly villas and beach houses

Pinnacle Pointe By Relaxtay | 600-acre Private Luxury Estate With Spa, Pool, Theater & Lake - Middletown, NY
10 3 reviews

Pinnacle Pointe By Relaxtay | 600-acre Private Luxury Estate With Spa, Pool, Theater & Lake

house, Bloomingburg
This waterfront villa in downtown Middletown offers a 15-mile drive to Highland Lake and a 12-mile drive to the Paramount Theatre.
This family-friendly estate accommodates 24 guests with 7 bedrooms and 8 bathrooms, featuring a private pool, hot tub, kayaking, golf, foosball, and table tennis.
Parkway House Goshen Bed And Breakfast Suite 2 - Middletown, NY
No reviews

Parkway House Goshen Bed And Breakfast Suite 2

house, Goshen
Parkway House Goshen Bed And Breakfast Suite 2 is located in Goshen, 14 miles from Stewart International Airport and 15 miles from Metro-North Harriman Station, with Bear Mountain State Park 23 miles away.
This recently renovated vacation home offers 8610 square feet of living space with 2 bedrooms, accommodating up to 11 guests, and features air conditioning, complimentary Wi-Fi, a garden, terrace, outdoor fireplace, and picnic area.
Villa Paraiso - Middletown, NY
10 1 review

Villa Paraiso

house, Florida
This Goshen villa is located 13 miles from Metro-North Harriman Station and 22 miles from Bear Mountain State Park.
This spacious 9710 square foot estate accommodates up to 19 guests with 2 bedrooms and 4 bathrooms, featuring a private pool, jacuzzi, bar, full kitchen, and complimentary WiFi.
New Farmhouse, King Beds, Game Room, Hot Tub & View! - Middletown, NY
10 2 reviews

New Farmhouse, King Beds, Game Room, Hot Tub & View!

house, Montgomery
This Montgomery, New York farmhouse is located 15 miles from the D.M. Weil Gallery, 21 miles from Loren Campbell Baseball Field and SUNY New Paltz, and 9.3 miles from Stewart International Airport, offering easy access to area attractions.
This 5,010-square-foot home boasts six bedrooms, five bathrooms, two living rooms, and can comfortably accommodate 22 guests, featuring a jacuzzi, fitness center, bar, and outdoor spaces including a terrace and garden, plus on-site activities like table tennis and darts.

Frequently Asked Questions about villa rentals in Middletown, NY

  • What are the must-see attractions in Middletown, NY?

    Middletown has a lot to offer! You should definitely check out the Orange County Historical Society Museum, which has a great collection of local artifacts. The Middletown Thrall Library is also worth a visit, especially if you're interested in architecture. And if you're looking for something a little more active, the Wallkill Valley Rail Trail is a great place for a walk or bike ride.
  • What are the best villa rentals in Middletown, NY?

  • What indoor activities for families are available in Middletown, NY on rainy days?

    On rainy days, families can head to the Middletown Thrall Library for story time or to browse the collection. The Orange County Historical Society Museum is also a good option, especially for kids who love history. For something a little more interactive, the YMCA of Middletown has a great indoor pool and fitness center.
  • What are the best villa rentals with a jacuzzi in Middletown, NY?

    The best villa rental with a jacuzzi in Middletown, NY is Beautiful Spacious House.

  • What are the best activities in Middletown, NY?

    Middletown has a lot to offer! For outdoor activities, the Wallkill Valley Rail Trail is a great place to go for a walk or bike ride. You can also check out the Minisink Battlefield for a glimpse into history. If you're looking for something a little more relaxing, the Middletown Thrall Library is a great place to spend an afternoon browsing books.
  • What are the best villa rentals for families and kids in Middletown, NY?

  • What are the advantages of renting a house or a villa in Middletown, NY

    Renting a house or a villa in Middletown gives you more space and privacy than a hotel. You'll also have access to a kitchen, which is great for families or groups who want to cook their own meals. And, of course, you'll have the added benefit of being able to relax in your own private space.
  • What are the best pet friendly villa rentals in Middletown, NY?

  • What food festivals or culinary events take place in and around Middletown, NY?

    There aren't many large food festivals in Middletown itself, but the surrounding area has a few options. The Hudson Valley Garlic Festival in Saugerties is a popular event, and the New Paltz Farmers Market is a great place to try local produce and artisanal food.
  • What are the best villa rentals with parking in Middletown, NY?

  • What exclusive experiences are available when visiting Middletown, NY?

    Middletown doesn't have a lot of exclusive experiences, but you can get a unique perspective by taking a guided tour of the Orange County Historical Society Museum. You can also arrange a private tour of the Wallkill Valley Rail Trail with a local guide.
  • Which part of Middletown, NY would be ideal for a villa rental?

    The area around Monhagen Park is a good choice for a villa rental, as it's quiet and residential with easy access to the Wallkill Valley Rail Trail and other attractions. The Town of Wallkill is another good option, as it has a more rural feel and is close to the Minisink Battlefield.

Popular destinations

Best Middletown, NY houses with a garden

Pond + Gazebo: Expansive Hudson Valley Escape! - Middletown, NY
No reviews

Pond + Gazebo: Expansive Hudson Valley Escape!

house, Goshen
This 4390 sq ft vacation home is located in the scenic Hudson Valley, offering convenient access to local attractions.
This spacious 5-bedroom, 4-bathroom property accommodates up to 27 guests and features a fully equipped kitchen, air conditioning, and on-site parking.
Pinnacle Pointe By Relaxtay 600 Acre Private Luxury Estate With Spa, Pool, Theater And Lake - Middletown, NY
No reviews

Pinnacle Pointe By Relaxtay 600 Acre Private Luxury Estate With Spa, Pool, Theater And Lake

house, Bloomingburg
This luxurious 600-acre private estate, Pinnacle Pointe, is located in High View, 23 miles from DM Weil Gallery and 25 miles from Mohonk Preserve.
This 9290 square feet villa offers 7 bedrooms, 7 bathrooms, a swimming pool, jacuzzi, sauna, fitness center, and accommodates up to 47 guests with amenities including a fridge, microwave, dishwasher, and Wi-Fi.
Luxury School House W/ Pool & Sauna -1 Hr From Nyc - Middletown, NY
10 73 reviews

Luxury School House W/ Pool & Sauna -1 Hr From Nyc

apartment, Unionville
This Unionville home is located in the mountains of New Hampton, just 6 miles from Pine Island Town Park and Scenic Farms Golf Course. It has received excellent ratings for user experience, location, and cleanliness.
This 4150 square foot house has 4 bedrooms, comfortably accommodating up to 8 guests. Amenities include a swimming pool, jacuzzi, sauna, fitness center, tennis court, and a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher.

Best Middletown, NY houses with parking

Nature Escape Studio - Sleeps 5 - Middletown, NY
10 4 reviews

Nature Escape Studio - Sleeps 5

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.

Best Holiday Houses with Swimming Pool in Middletown, NY

Enjoy a proper swim in the heart of the city. These vacation homes in Middletown, NY include pool access for your daily routine.

Pinnacle Pointe | Year-round Pool Spa Lake Theater - Middletown, NY
9.8 10 reviews

Pinnacle Pointe | Year-round Pool Spa Lake Theater

house, Bloomingburg
Luxury School House W/ Pool & Sauna -1 Hr From Nyc - Middletown, NY
10 73 reviews

Luxury School House W/ Pool & Sauna -1 Hr From Nyc

apartment, Unionville
Villa Paraiso - Middletown, NY
10 1 review

Villa Paraiso

house, Florida
Pinnacle Pointe By Relaxtay 600 Acre Private Luxury Estate With Spa, Pool, Theater And Lake - Middletown, NY
No reviews

Pinnacle Pointe By Relaxtay 600 Acre Private Luxury Estate With Spa, Pool, Theater And Lake

house, Bloomingburg

Check Out Luxury Vacation Homes in Middletown, NY

A well-chosen luxury vacation home in Middletown, NY makes the trip. Discover high-end rooms and a location worth the journey.

Hudson Valley Horse Farm Stay | 10 Min To Legoland - Middletown, NY
10 12 reviews

Hudson Valley Horse Farm Stay | 10 Min To Legoland

gîte, Scotchtown

Choose the Right Vacation Homes with a Hot Tub in Middletown, NY

Enjoy a private hot tub at your city vacation home in Middletown, NY. These properties offer a secluded soak after a day of exploration.

Pool, Fire Pit Bedroom & Alaska King Sleeps 16 - Middletown, NY
No reviews

Pool, Fire Pit Bedroom & Alaska King Sleeps 16

house, Chester
Pinnacle Pointe | Year-round Pool Spa Lake Theater - Middletown, NY
9.8 10 reviews

Pinnacle Pointe | Year-round Pool Spa Lake Theater

house, Bloomingburg
New Farmhouse, King Beds, Game Room, Hot Tub & View! - Middletown, NY
10 2 reviews

New Farmhouse, King Beds, Game Room, Hot Tub & View!

house, Montgomery
Pinnacle Pointe By Relaxtay | 600-acre Private Luxury Estate With Spa, Pool, Theater & Lake - Middletown, NY
10 3 reviews

Pinnacle Pointe By Relaxtay | 600-acre Private Luxury Estate With Spa, Pool, Theater & Lake

house, Bloomingburg
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