Best Vacation rentals and Airbnb offers in Middletown, NY
9.8 98 reviews
Middletown, NY
07/22 – 07/26
$236/nighttotal: $944 (4 )
2 Unit Condo Minutes From Lego Land
2 2
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.
10 5 reviews
Middletown, NY
07/22 – 07/26
$175/nighttotal: $700 (4 )
Cozy Downtown Studio W/ Kitchen & Workspace
1 2
apartment , Middletown
This studio suite is centrally located in Middletown's downtown district, offering convenient access to dining, cafes, breweries, and essential services, with proximity to Touro College and Garnet Health Medical Center. This apartment features a fully equipped kitchen with modern appliances, air conditioning, free on-site parking, and accommodates up to 2 guests with self-check-in via a smart lock.
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.
10 6 reviews
Middletown, NY
07/22 – 07/26
$114/nighttotal: $456 (4 )
9 Person Glamping Tent- Dreamweaver
1 2
glamping , Scotchtown
This glamping site in Scotchtown offers a peaceful natural setting, just minutes from Middletown's shopping and dining, and a short drive to Legoland and local wineries. This accommodation accommodates up to 9 guests and features solar electricity, a private outdoor area, and shared pool access, with optional activities like a ropes course and paintball available for purchase.
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.
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.
Middletown, NY
07/22 – 07/26
$146/nighttotal: $584 (4 )
Cottage Suites
1 2
cottage , Middletown
Cottage Suites in Middletown offers a secluded getaway within walking distance of Middletown's city center. This one-bedroom cottage sleeps two guests and includes a fridge, microwave, free on-site parking, and internet access; a $250 security deposit is required.
Middletown, NY
06/27 – 07/04
$537/nighttotal: $3759 (7 )
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.
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.
9.7 64 reviews
Middletown, NY
07/22 – 07/26
$102/nighttotal: $408 (4 )
Victor-amazing Glamping Experience-middletown Ny
1 2
glamping , Scotchtown
This Scotchtown glamping experience offers a private, quiet setting just minutes from Middletown's shopping and dining, and is a short drive to Legoland and local wineries. This accommodation accommodates up to 8 guests and features a private outdoor area with seating, a grill, and hammocks, along with access to a shared swimming pool with a slide, discounted adventure activities like a ropes course, and portable bathrooms with nearby flushing toilets and showers.
9.4 13 reviews
Middletown, NY
08/21 – 08/23
$453/nighttotal: $906 (2 )
Blooming Tranquil Getaway
1 5
apartment , Bloomingburg
This Bloomingburg apartment rental is conveniently located a ten-minute drive from NY State Route 20, offering easy access to attractions like Woodbury Common Premium Outlets, Bethel Woods Center for the Arts, Legoland New York, and various casinos within a 20-mile radius. The spacious bi-level unit features three bedrooms sleeping up to six guests, two bathrooms, a fully equipped kitchen with dishwasher, a private garden with a deck, fire pit, and propane grill, plus keyless entry and free parking.
9.1 52 reviews
Middletown, NY
08/21 – 08/23
$375/nighttotal: $750 (2 )
Cozy Apartment Near Legoland!
1 5
apartment , Goshen
This Goshen apartment is conveniently located near Legoland, just minutes away from Woodbury Common outlets and Bear Mountain, offering easy access to popular attractions and shopping. This rental consistently receives excellent ratings for location, cleanliness, and overall user experience. The apartment comfortably accommodates up to six guests with two full beds, a queen bed, a sofa, and a futon. Guests can enjoy modern amenities such as a flat-screen TV, a fully equipped kitchen, and bathroom essentials, all while enjoying a relaxing vacation near Legoland.
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.
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.
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.
9.5 4 reviews
Middletown, NY
08/21 – 08/23
$1073/nighttotal: $2146 (2 )
The Cathedral Barn
3 5
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.
9.5 23 reviews
Middletown, NY
06/27 – 07/04
$192/nighttotal: $1344 (7 )
Escape To A Streamside Cabin In The Lower Catskills
1 2
cabin , Wurtsboro
This Wurtsboro, Lower Catskills streamside cottage is located 22 miles from the D.M. Weil Gallery and 30 miles from Historic Huguenot Street, offering easy access to hiking trails. The 450-square-foot one-bedroom, one-bathroom dwelling sleeps two guests and features a fully equipped kitchen, Wi-Fi, private parking, a washing machine, and an outdoor fireplace.
Best Middletown, NY vacation rentals with parking
Middletown, NY
08/21 – 08/23
$515/nighttotal: $1030 (2 )
Hike, Ski & Explore: Otisville Retreat W/ Yard!
1 5
house , Otisville
This Otisville vacation home is situated approximately 27 miles from DM Weil Gallery and Stewart International Airport, and around 29 to 30 miles from Mohonk Preserve and Metro-North Harriman Station. This 2080 square foot, 4-bedroom dwelling accommodates up to 13 guests with 3 bathrooms, a fully equipped kitchen, air conditioning, WiFi, and a garden, offering an ideal base for outdoor enthusiasts exploring the Otisville area.
9.8 6 reviews
Middletown, NY
08/21 – 08/23
$378/nighttotal: $756 (2 )
Abomb! Adorable 2-bdrm Chalet With Lots Of Room!
2 5
chalet , Wurtsboro
This Wurtsboro, New York chalet is located within 3 miles of Mamakating Library, Veteran's Memorial Park, Sullivan County Parks & Recreation, Masten Lake, and the Mamakating Farmers Market, offering easy access to local attractions and amenities. This two-bedroom, one-bathroom cabin sleeps six and features a kitchen with a fridge and microwave, air conditioning, a terrace, a garden, a spa, parking, and internet access; barbecue grills are available for guest use.
Middletown, NY
06/27 – 07/04
$514/nighttotal: $3598 (7 )
Elegant Town Home Middletown Suburb Close To City
3 2
apartment , Washington Heights
This modern vacation rental is located in Middletown, New York, just a short drive from Washington Heights and its attractions like the Paramount Theatre and Museum Village. The house offers a comfortable and relaxing escape from the city, with easy access to local wineries, breweries, and historical sites. The three-bedroom, three-bathroom home provides plenty of space for families or groups. Enjoy modern appliances, a Jacuzzi, and a private parking space.
9.5 150 reviews
Middletown, NY
08/21 – 08/23
$401/nighttotal: $802 (2 )
Beautiful Log Cabin Style House
1 5
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.
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?
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?
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.
Middletown, NY
06/27 – 07/04
$537/nighttotal: $3759 (7 )
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.
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.
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.
9.7 13 reviews
Middletown, NY
07/22 – 07/26
$100/nighttotal: $400 (4 )
9 Person Glamping Tent- Chipmunk
1 2
glamping , Scotchtown
This glamping site is situated near Scotchtown, New York, offering convenient access to attractions such as Legoland, which is approximately 10 miles away. This spacious glamping experience accommodates up to 9 guests, featuring a private outdoor area with seating and hammocks, a shared swimming pool, a jacuzzi, and portable toilets and showers, with nearby access to flushing facilities.
9.5 21 reviews
Middletown, NY
07/22 – 07/26
$358/nighttotal: $1432 (4 )
The Cottage Farmhouse
1 2
farm , Middletown
This farm is located in Middletown, just a short distance from major attractions. It has excellent user ratings for location, cleanliness, and overall experience. The property features a comfortable and spacious layout that can accommodate up to 6 guests. Amenities include a fully equipped kitchen, a garden, a fitness center, and a picturesque setting perfect for relaxing and enjoying the outdoors.
9.5 4 reviews
Middletown, NY
08/21 – 08/23
$343/nighttotal: $686 (2 )
Cozy Delight Home
1 5
apartment , Scotchtown
This Scotchtown apartment rental, centrally located in Scotchtown, offers easy access to local attractions—though specific distances require further clarification. The 3-bedroom, 1-bathroom unit sleeps 6, features a king-size bed in one bedroom, and includes amenities such as internet, air conditioning, a kitchen, parking, and a fitness center; further details on the apartment's size, specific layout, and nearby activities are needed.
Middletown, NY
07/22 – 07/26
$492/nighttotal: $1968 (4 )
Family Getaway Near Hudson Valley Attractions
1 2
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.