Family-friendly vacation rentals in Middletown

Country Quiet

Our beautiful, rustic horse farm offers a newly renovated 3 bedroom, 1 bath home that sits at the end of a 700-foot private driveway across from the main house & horse barn. Lots to do in this area; minutes away from LEGOLAND, hiking/biking at Sam's Point & Winding Hills Park & Lake, Bethel Woods, Stony Ford & Wallkill Golf, Holiday Mountain Ski & Fun Park, Oakland Valley Race Park, Monticello Raceway, Resorts World Casino, Goshen Historic Track, Angry Orchard Winery as well as JW New World HQ.

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Modena Mad House

Our apartment is 6 miles from downtown New Paltz on a quiet and private setting only 1.5 hours from New York City, in the heart of Hudson Valley's Wine Country and apple/peach orchards. 1 bedroom apartment with separate kitchen living room and front porch. Fridge is stocked with eggs, bread, cheese, coffee, wine. We have a large HD screen TV and Roku, but no local cable. 7 miles from Mohonk Preserve and 10 miles from Gunks climbing area, and great Cross-country skiing. Self check-in

Dream House in the Gunks

This cozy House is located on top of the Gunks a few miles away from Minnewaska State Park main entry. House is facing State forest and is a perfect getaway from hectic city life. The space has been carefully redesigned with a lot of details for guests to enjoy the stay. We are very serious about the cleaning/laundry process. Fast internet, complimentary high quality coffee and tea, natural body wash/shampoo. There are good restaurants, wineries, farms and great outdoor activities around.

Δ Scenic Hiking Paradise with Deck and Fire Pit!

Relax at this peaceful place atop the Shawangunk Mountain Ridge. You'll enjoy plenty of room at this wooded oasis! • On 2 wooded acres • Beautiful area • Deck off kitchen w nice grill • Lawn fire pit w seating & string lights • Adjacent to 1600 acres of State Forest with official hiking trails & Amazing Views right near house • Professional Cleaning • Home Gym • 3 bedrooms • Large living room with 2 sleeper sofas • Near great outdoor and indoor attractions

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

<The Painted House> Local Hiking/Garden views/Golf

<The Painted House> The house is on a 1 acre lot with a magnificent and magical perennial garden. I love decorating the space with my fun and eclectic finds. Warwick Permit #34239 Please feel free to inquire if you are traveling with more than 4 guests. Check out my Neighboring listings for more unique stays in Warwick, NY ! -Rabbit hill Cabin -3bedrooms Airbnb.com/h/rabbithillcabin -Pisces Pond Cabin-2bedrooms Airbnb.com/h/piscespondcabin

Luxury Apt/Sugar Loaf/10 Min To LEGOLAND

This lovely modern space was just built in 2015. The space is located in the quaint Hamlet of Sugar Loaf, New York Artisan Village, which is surrounded by the town of Warwick and Chester with Greenwood Lake just minutes away...and NYC is just 75 minutes. It's a second floor apartment with private front and back entrances. Rear deck overlooks spacious fenced in yard with pond view. Walking distance to 2 restaurants and deli. LEGOLAND just 8 miles!

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.