Family-friendly holiday rentals in Middletown

Studio in Cornwall

Located near the village, hiking trails, Jones Farm, Hudson River, Woodbury Commons, West Point and more. The studio is ground level with a private entrance. The kitchenette incudes a convection toaster oven, a hot plate cooktop with pots/pans, light kitchenware, coffee maker, & fridge. Also provided: TV, Roku stick, Wi-Fi, AC/electric heat. (No cable) This is our home. The use of illicit drugs, smoking and excessive alcohol is prohibited. We live here with kids/dogs so you may hear us moving

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

School Bus Glamp w/HotTub~15min to Gunks/New Paltz

Experience a unique stay in a magic school bus on 10 acres! 15min to Gunks, New Paltz, Angry Orchard HQ, Minnewaska &more! Relax in the hot tub in the morning or sit under the stars at night. Two beds; twin & full w/bedding. Heater/AC, mini-fridge, Keurig w/coffee & mugs. Swing set & trampoline for kids. Private outdoor set up w/(year-round) hot tub, dining area, fresh water sink & fire pit await you. Wonderful bakery & outdoor store just down the road. Enjoy Gunks glamping with a relaxing spa!

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

Great apartment- closest to Legoland

Large studio apartment in an historic luxury setting. Guests have a private entrance with parking to a first floor, fun studio. Our property boasts a private tennis/pickleball court for guest use and is situated directly on the Heritage Trail, which is perfect for biking and jogging. Our home borders several hundred acres of scenic rural property, yet we are conveniently located in the charming, historic Village of Goshen - within walking distance to restaurants and the Trotting Horse Museum

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, French door shower, and a kitchenette with sunny breakfast nook. It's freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Just Around The Corner

This roomy, modern and immaculate apartment is situated conveniently near town, but far enough away that you can enjoy the countryside. Enjoy the view of the pond and sounds of nature. A one bedroom that sleeps six with three queen beds in separate rooms divided by doors. (Please note the listing price is for 4 guests. Each additional guest is $25 per night). We are 6 min to Middletown, 18 min to Legoland, 21 min to Wallkill, 49 min to Warwick and just under one hour to Patterson, NY.

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Canyon Edge off - grid Bungalow

The ideal perch to reflect, connect, and participate in nature's beauty. This unique structure blends pure nature with simple comfort. Sitting canyon side, you sleep beneath the canopy and wake to the mountains of the Hudson Valley. Welcome the spring buds of our forest oaks; Make summertime memories into the night by the fireside; Enjoy natures fall masterpiece of changing of the leave; Reflect on the year as the snowflakes fall Read listing fully, we’re available for any Q’s!

Peace and quiet. Comfy, private house to relax in

Quiet property,almost 8 acres, of beautiful wooded property . Set back from the road. Many trails, wineries and breweries nearby. Legoland is 20 minutes away and many antique shops within 30 minutes or so. We live in the other house on the property, so we are accessible. You can take a stroll on the path by the stream or sit on the spacious 35 x 10 foot deck and enjoy the natural setting of the property. Fire pit is now available. Enjoy the night air and gaze at the stars.

Sunny Loft Morning Muffin Basket

Experience exceptional quality in a homey B&B atmosphere Features - Morning muffins/cookies in your room - Coffee bar, teas, hot cocoa - 2 Super comfy queen sized beds. - Huge bathroom - Heated Jacuzzi bathtub - Seated shower - Private driveway. Private entrance - Parking at door. - Writing desk. - Wifi - 5 min SKAC -12 min USMA -10 min Woodbury Common -10 min Stewart Airport -25 min Beacon-DIA-Metro -Must be 25 years or older to book. No parties. extra guests inquire

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Picture this... You escape to a relaxing, picturesque, and peaceful country cottage and enjoy some of your favorite convenience amenities like 1 Gig Wifi and your favorite streaming sources. Just 10 minutes to LEGOLAND, 3 miles to the famous Orange Heritage Trail, and less than 20 minutes to America's oldest winery, Brotherhood, this cottage has something to offer for everyone. You'll be minutes from conveniences like Target but taking in the views, you'd never know it.