Holiday Rentals in Middletown, NY

29 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • bookabach
  • expedia
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelscom
  • hotelopia
Middletown, NY holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

Hudson Valley Horse Farm Stay | 10 Min To Legoland - Middletown, NY
10 6 reviews
Middletown, NY
22/07 – 26/07
NZ$718/nightTotal: NZ$2872 (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.
A Hudson Valley Barn Celebration - Middletown, NY
10 1 review
Middletown, NY
22/07 – 26/07
NZ$1246/nightTotal: NZ$4984 (4 )

A Hudson Valley Barn Celebration

1 2
farm , Middletown
This Middletown farmhouse, sleeping up to 16 guests, is situated in [Insert District Name, Middletown] – precise location details upon request.
The 6-bedroom, 4-bathroom property boasts a fully equipped kitchen, Jacuzzi, fitness centre, and garden, offering ample space and modern amenities for a comfortable stay.
The Cathedral Barn - Middletown, NY
9.5 4 reviews
Middletown, NY
22/07 – 26/07
NZ$1100/nightTotal: NZ$4400 (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).
The Cottage Farmhouse - Middletown, NY
9.5 21 reviews
Middletown, NY
22/07 – 26/07
NZ$616/nightTotal: NZ$2464 (4 )

The Cottage Farmhouse

1 2
farm , Middletown
This charming farm stay is situated in Middletown, just a short distance from the town's main attractions and historical landmarks. It enjoys excellent ratings for cleanliness, location and user experience.
This welcoming property can accommodate up to six guests and features a fully equipped kitchen, a comfortable living area, two bathrooms and a lovely garden. Guests can enjoy a range of amenities, including internet access, air conditioning, parking and a fitness centre.

Best Middletown, NY holiday rentals with parking

Cottage Suites - Middletown, NY
Middletown, NY
22/07 – 26/07
NZ$251/nightTotal: NZ$1004 (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.
Huge Retreat W Alaska King, Pool & Jacuzzi Tub Indoor - Middletown, NY
Middletown, NY
21/08 – 23/08
NZ$2608/nightTotal: NZ$5216 (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.
Escape To A Streamside Cabin In The Lower Catskills - Middletown, NY
9.6 20 reviews
Middletown, NY
27/06 – 04/07
NZ$368/nightTotal: NZ$2576 (7 )

Escape To A Streamside Cabin In The Lower Catskills

1 2
cabin , Wurtsboro
This Wurtsboro cottage is conveniently located less than 1.6km from Veteran's Memorial Park and the Mamakating Library, and within 3.2km of Sullivan County Parks & Recreation and the Mamakating Farmers Market.
The 42-square-metre self-catering lodge sleeps two guests, boasting a fully equipped kitchen, a washing machine, a fireplace, a Smart TV, and a barbecue; enjoy the smoke-free environment and excellent user ratings.
Private Glamping Tent For 2 - Middletown, NY
9.5 11 reviews
Middletown, NY
22/07 – 26/07
NZ$201/nightTotal: NZ$804 (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.

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, near the Thrall Park and the Middletown Thrall Library, is a great choice for a vacation rental. It's within walking distance of many shops, restaurants, and attractions.
  • What are the best Airbnb and holiday rentals in Middletown, NY?

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

    The Orange County Arboretum is a great place for families, with its beautiful gardens and interactive exhibits. The Middletown Thrall Library also has a fantastic children's section with regular events and activities.
  • What are the most popular Airbnbs in Middletown, NY?

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

    To avoid the crowds and get the best deals, it's best to book your vacation rental in Middletown during the shoulder seasons, like spring or autumn. You'll enjoy pleasant weather and fewer tourists.
  • 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?

    Take a stroll through the beautiful grounds of SUNY Orange. Explore the historic downtown and browse the independent shops. Enjoy a picnic lunch at Thrall Park, which offers stunning views of the city.
  • What are the best rentals for families and kids in Middletown, NY?

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

    For a taste of local cuisine, try the popular 'The Black Cat' for their delicious burgers and classic American dishes. 'The Cornerstone' offers a more upscale dining experience with fresh, seasonal ingredients.
  • 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 scenic Wallkill Valley Rail Trail is a great option for walking or cycling. It runs through the heart of the city, offering beautiful views of the Wallkill River and surrounding countryside. You can also explore the historic downtown area on foot, taking in the architecture and charming shops.
  • Are there pet-friendly attractions in Middletown, NY?

    Thrall Park is a great place to bring your furry friend for a walk. The Orange County Arboretum also welcomes well-behaved dogs on leash.
  • What are the benefits of choosing a vacation rental in Middletown, NY?

    Vacation rentals offer more space and privacy than a hotel room. They also often come with a kitchen, allowing you to cook your own meals and save money. Many rentals are located in quiet, residential neighbourhoods, providing a more authentic experience.

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
NZ$2608/nightTotal: NZ$5216 (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
22/07 – 26/07
NZ$1088/nightTotal: NZ$4352 (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).

Best pet friendly Middletown, NY holiday rentals

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

Hike, Ski And Explore Otisville Retreat With Yard! - Middletown, NY
Middletown, NY
21/08 – 23/08
NZ$886/nightTotal: NZ$1772 (2 )

Hike, Ski And Explore Otisville Retreat With 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.
Nature Escape Studio - Sleeps 5 - Middletown, NY
10 4 reviews
Middletown, NY
22/07 – 26/07
NZ$467/nightTotal: NZ$1868 (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.
Cozy Delight Home - Middletown, NY
9.5 4 reviews
Middletown, NY
21/08 – 23/08
NZ$589/nightTotal: NZ$1178 (2 )

Cozy Delight Home

1 5
apartment , Scotchtown
This three-bedroom Scotchtown apartment, perfect for families or groups of up to six, offers convenient access to local attractions, although precise distances are unspecified.
The self-catering flat features a king-size bed in one bedroom, a fitness centre, parking, and internet access; further details regarding the property's size and specific interior design are unavailable.
9 Person Glamping Tent- Dreamweaver - Middletown, NY
10 6 reviews
Middletown, NY
22/07 – 26/07
NZ$195/nightTotal: NZ$780 (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.
©2026 cozycozy.com