
Family-friendly vacation rentals in Middletown
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Middletown

Nightly prices starting at
Middletown vacation rentals start at G$10,460 GYD per night before taxes and fees

Verified guest reviews
Over 40 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Middletown rentals

4.6 Average rating
Middletown stays receive an average rating of 4.6 out of 5 from guests
Top-rated family-friendly rentals in Middletown
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.
4.94 out of 5 average rating, 582 reviews
Spacious A-Frame Getaway near Hiking and Wineries
Escape to our A-frame in the heart of the Shawangunks, nestled within the picturesque Hudson Valley. Just 1.5-2 hours from NYC, our spacious and serene home is perfect for a peaceful retreat, outdoor adventures, and exploring local wineries. Nearby attractions include Lake Minnewaska Park, Mohonk Preserve, Sam’s Point, the Shawangunk Wine Trail, Ellenville and Blue Cliff Monastery. The location also provides convenient access to explore many of the Hudson Valley and Catskill towns and villages.
4.97 out of 5 average rating, 142 reviews
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.
4.81 out of 5 average rating, 136 reviews
Serene Private Home • Light-Filled • Hot Tub •Deck
Spacious 3,600 sq ft home designed for comfort and ease in upstate New York 🌿 Light-filled rooms, open flow, and a hot tub + deck create a calm, elevated stay ✨ An open layout with multiple living areas makes it easy to gather while still having space to relax and unwind & enjoy throughout. The space functions as a self-contained part of a larger property, offering privacy and independence without feeling segmented. A comfortable base near farms, villages, dining, and outdoor activities.
4.92 out of 5 average rating, 167 reviews
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!"
4.9 out of 5 average rating, 109 reviews
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
4.96 out of 5 average rating, 123 reviews
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!
4.85 out of 5 average rating, 372 reviews
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.
4.94 out of 5 average rating, 405 reviews
Spacious 6BR Villa | Serene Scenic Mountain Escape
Escape to this spacious 6-bedroom mountain villa, a peaceful retreat perfect for families and groups. Just about 1 hour from New York City, enjoy beautiful scenic views, comfortable living spaces, a well-equipped home, and plenty of outdoor space. Explore nearby hiking trails and local attractions, or simply relax and enjoy the quiet surroundings. Whether you're planning a family getaway or a weekend with friends, it's the perfect place to unwind, reconnect, and make lasting memories.
4.87 out of 5 average rating, 114 reviews
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.
4.87 out of 5 average rating, 220 reviews
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.
4.98 out of 5 average rating, 220 reviews
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.
4.97 out of 5 average rating, 110 reviewsPopular amenities for Middletown family-friendly rentals
Family-friendly home rentals with a hot tub

Riverfront Retreat | Hot Tub, Firepit & Pool Table
4.97 out of 5 average rating, 126 reviews
Forest Spa Retreat on Cascading Brook • 90 Min NYC
4.95 out of 5 average rating, 456 reviews
Mountain Creek Appalachian Condo Waterpark
4.96 out of 5 average rating, 163 reviews
Mountain Creek sanctuary pool & hot tub
4.94 out of 5 average rating, 115 reviews
Pocono Castle: Dungeon Escape Room & Private Pond
4.99 out of 5 average rating, 475 reviews
Luxury Villa w Lake View & Private Heated Pool
4.91 out of 5 average rating, 116 reviews
Creek, Sauna, Hot Tub, Fire Pit & Pet-Friendly
4.97 out of 5 average rating, 207 reviews
Catskills Cabin, Hot Tub, Wood Stove, King Bed
4.98 out of 5 average rating, 232 reviewsFamily- and pet-friendly home rentals

Modern 3BR BoHo Retreat/Nearby Hiking, Wineries
4.93 out of 5 average rating, 133 reviews
Catskills Barn Retreat w/Fireplace & 9 Acres
4.94 out of 5 average rating, 130 reviews
Hiker’s Haven, a Cozy Cabin above Bashakill Refuge
4.92 out of 5 average rating, 140 reviews
Luxurious Cozy Mountain Retreat 2BR-2BA - Ski/Spa.
4.98 out of 5 average rating, 122 reviews
Gorgeous Chalet with Lots of Room!
4.96 out of 5 average rating, 249 reviews
Balmville Mid-Century Gem & Work From Home Retreat
4.99 out of 5 average rating, 210 reviews
Dave's Milk Barn
4.88 out of 5 average rating, 1093 reviews
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor
4.93 out of 5 average rating, 106 reviewsFamily-friendly home rentals with a pool

Discounted 1 Bed *patio closed during construction
4.93 out of 5 average rating, 192 reviews
Golf Sim! Hot Tub/Game Room/Cinema 2 Kings
4.99 out of 5 average rating, 145 reviews
9BR Log Cabin Home w/ Hot Tub & Swimmable Pond
4.86 out of 5 average rating, 117 reviews
Farmhouse w/ Pool, Sauna & Hot Tub near Storm King
5.0 out of 5 average rating, 105 reviews
Beautiful Retreat w/Pool, Hot Tub & Fire Pit, 6 BR
4.91 out of 5 average rating, 144 reviews
Hillside villa with 9-mile lake views
4.97 out of 5 average rating, 108 reviews
Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!
4.96 out of 5 average rating, 141 reviews
Appalachian Lodge Top Floor w/views
4.94 out of 5 average rating, 950 reviewsDestinations to explore
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- Mountain Creek Resort
- Yankee Stadium
- American Dream
- MetLife Stadium
- Bushkill Falls
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Bethel Woods Center for the Arts
- Delaware Water Gap National Recreation Area
- Nickelodeon Universe
- Resorts World Catskills
- Promised Land State Park
- Storm King Art Center
- Mohonk Preserve
- Mountain Creek Water Park
- Peekamoose Blue Hole
- Brotherhood, America's Oldest Winery
- Harriman State Park
- Mount Peter Ski Area
- Wawayanda State Park
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