Family-friendly vacation rentals in Middletown

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 4 people.

Indoor spaces · Family · Long stay

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

Family · Kitchen · Layout

Mountain View Retreat w/ Hot Tub, Theater, and Gym

Thoughtfully designed, this secluded retreat is nestled on 12 acres of picturesque land in Warwick, NY. The exquisite home offers the perfect blend of luxury and tranquility, making it an ideal getaway for families and friends. Highlights include: -Huge deck with mountain views -115" 4k projection theater w/ seating for 10, wet bar, & popcorn machine -Hot tub w/ seating for 7 -Gym w/ indoor endless lap pool, Peloton bike, and yoga equipment -Game room w/ billiards & Pac-man -Gourmet kitchen

Family · Indoor spaces · Skiing

Quiet Homey Rustic Retreat

"Escape to the perfect blend of tranquility and excitement! This charming 3-bedroom log cabin, just 120 minutes from the hustle and bustle of New York City, offers the ideal retreat. Nestled 15 minutes from Resort Casino, 10 minutes from the vibrant Middletown shopping area, and a short drive to Woodbury Commons, Warwick, and Robberio Winery. Plus, family fun awaits just 20 minutes away at Lego Land. Your rustic haven awaits, where city convenience meets the serenity of a log cabin retreat!"

Family · Indoor spaces · Amenities

Carriage House Apartment Close to Legoland NY

Immerse yourself in history in our newly renovated Carriage House, originally a historic horse barn, ensconced with hand hewn, exposed beams. This unique accommodation boasts modern amenities such as central air conditioning, a cozy fireplace, private laundry, and a fully working kitchen. Situated just a 4-minute drive from the renowned Legoland and opposite the prestigious Goshen Historic Race Track, we are perfectly positioned for both convenience and entertainment. @parkwayhousegoshen

Family · Kitchen · Decor

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Indoor spaces · Kitchen · Checkout

Serene Victorian Guest Apartment with Clawfoot Tub

Escape to a stunningly renovated private 3rd-floor apartment in a 6000 sq ft. 1883 Victorian Manor in Blooming Grove, NY. Designed for 1–6 guests, this light-filled space offers comfort and classic charm in a peaceful country setting. Includes luxe beds, a clawfoot tub, French-door shower, and kitchenette with sunny breakfast nook. An ideal sanctuary. Views of wildflowers, quiet country, and cows next door. 3rd Floor up two staircases, rewarded with a stunning space and elevated views.

Kitchen · Indoor spaces · Hospitality

Renovated 2 Bedroom Apartment in Heart of Village

Our newly renovated apartment is the lower level of a 1920 Victorian in the heart of the Village of Warwick. It boasts 650 sq ft of space with 2 bedrooms, and a full kitchen and bath. You can walk to beautiful shops, parks, and restaurants, or drive (free off-street parking) only minutes to ski, golf, hike, or enjoy our local orchards and wineries. There's even a doughnut shop across the street! All this with a huge backyard with it's own babbling creek! Welcome to 69 South St.

Indoor spaces · Kitchen · Access

Mountain Creek Appalachian Condo Waterpark

Relax in the most convenient Condo in Appalachian Hotel with the whole family at this one bedroom apartment, peaceful place to stay. All amenities Resort just at walking distance to Mountain Creek Ski Slope!!, 1st Floor one bedroom apartment just in front of the pool , jacuzzi and sauna facilities! Ski lift Sugar quad is close to the condo’s backyard,cable tv. As of March 2026, The Appalachian started a garage renovation project and also includes the small parking area up top.

Indoor spaces · Kitchen · Condition

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.

Indoor spaces · Family · Sleep quality

Historic Hudson Valley Farm House

This lovely historic farm house in the heart of the Hudson Valley is the perfect location for your next get away. The relaxation begins as you turn onto our long private drive, watch for wild turkey and deer. This is the perfect spot if you are coming to the area for a wedding, to visit West Point or LEGOLAND, go hiking, skiing or just to sample the local craft breweries and wineries. For art and music lovers Storm King Art Center, Dia Beacon and Bethel Woods are nearby.

Indoor spaces · Family · Comfort

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.

Indoor spaces · Kitchen · Nearby