
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.
Indoor spacesKitchenQuiet
4.94 out of 5 average rating, 582 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.
FamilyKitchenBathroom
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.
FamilyKitchenLong stay
4.92 out of 5 average rating, 167 reviews
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
KitchenFamilyNearby
4.99 out of 5 average rating, 186 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!"
FamilyIndoor spacesGetting around
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
KitchenFamilyNearby
4.96 out of 5 average rating, 123 reviews
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.
FamilyIndoor spacesSkiing
4.92 out of 5 average rating, 346 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.
KitchenFamilyWifi
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.
Indoor spacesFamilyNearby
4.87 out of 5 average rating, 114 reviews
Modern 3BR BoHo Retreat/Nearby Hiking, Wineries
Our newly modern bohemian cottage (aka Green House!) is perfect for your next weekend getaway or a new WFH locale. Decompress from city stress in this calm, serenely appointed private home. Close to attractions but far enough away to escape, you'll never want to leave. NYC: 79 mi. Hunter Mountain Ski Resort: 60 mi. Pine Bush - groceries/supplies: 7 mi. Middletown - shopping (Walmart, Target, Best Buy, Home Depot): 16 mi. Hiking trails: 7 mi. Horseback riding: 7 mi. Sky diving: 15 mi.
Indoor spacesKitchenDecor
4.93 out of 5 average rating, 133 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.
FamilyIndoor spacesHospitality
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.
FamilyKitchenComfort
4.98 out of 5 average rating, 220 reviewsPopular amenities for Middletown family-friendly rentals
Family-friendly home rentals with a hot tub

Mountain Creek sanctuary pool & hot tub
Indoor spacesKitchenBathroom
4.94 out of 5 average rating, 115 reviews
Creek, Sauna, Hot Tub, Fire Pit & Pet-Friendly
FamilyKitchenLocation
4.97 out of 5 average rating, 206 reviews
Mountain Creek Appalachian Condo Waterpark
KitchenFamilyPool
4.96 out of 5 average rating, 162 reviews
Luxury Villa w Lake View & Private Heated Pool
KitchenFamilyCondition
4.91 out of 5 average rating, 116 reviews
Legoland Mt Peter 3BR Pool Theater Hot Tub 1Pet
KitchenFamilySolo travel
4.96 out of 5 average rating, 106 reviews
Forest Spa Retreat on Cascading Brook • 90 Min NYC
Indoor spacesFamilyView
4.95 out of 5 average rating, 456 reviews
NEW! Foley's Riverfront w/ Hot Tub-LEGO LAND CLOSE
FamilyIndoor spacesLocation
4.89 out of 5 average rating, 233 reviews
Pocono Castle: Dungeon Escape Room & Private Pond
KitchenFamilyCleanliness
4.99 out of 5 average rating, 475 reviewsFamily- and pet-friendly home rentals

Spacious A-Frame Getaway near Hiking and Wineries
Indoor spacesFamilyAmenities
4.97 out of 5 average rating, 142 reviews
Catskills Barn Retreat w/Fireplace & 9 Acres
Indoor spacesFamilyCondition
4.94 out of 5 average rating, 130 reviews
Unwind in a Bespoke Downtown Studio W Laundry
Indoor spacesFamilyAir conditioning
4.85 out of 5 average rating, 372 reviews
Hiker’s Haven, a Cozy Cabin above Bashakill Refuge
KitchenFamilyCleanliness
4.92 out of 5 average rating, 140 reviews
Luxurious Cozy Mountain Retreat 2BR-2BA - Ski/Spa.
Indoor spacesKitchenWifi
4.98 out of 5 average rating, 122 reviews
Gorgeous Chalet with Lots of Room!
Indoor spacesKitchenAir conditioning
4.96 out of 5 average rating, 249 reviews
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor
FamilyKitchenCondition
4.95 out of 5 average rating, 105 reviews
Balmville Mid-Century Gem & Work From Home Retreat
FamilyKitchenWifi
4.99 out of 5 average rating, 210 reviewsFamily-friendly home rentals with a pool

Discounted 1 Bed *patio closed during construction
FamilyKitchenCheck-in
4.93 out of 5 average rating, 191 reviews
Hillside villa with 9-mile lake views
KitchenFamilyAccuracy
4.97 out of 5 average rating, 108 reviews
Farmhouse w/ Pool, Sauna & Hot Tub near Storm King
FamilyIndoor spacesLocation
5.0 out of 5 average rating, 105 reviews
Historic Cabin with Pool and Fire Pit
KitchenIndoor spacesParking
4.94 out of 5 average rating, 105 reviews
Indoor Heated Pool + Sauna + Creek, Spacious 4Bdrm
Indoor spacesFamilyRiver
4.89 out of 5 average rating, 181 reviews
Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!
Indoor spacesKitchenBathroom
4.96 out of 5 average rating, 141 reviews
Spacious Catskills Farmhouse on over 5 acres!
KitchenFamilyValue
4.91 out of 5 average rating, 125 reviews
Walk to Waterpark | Mtn Views Pool Hot Tub 324
Indoor spacesFamilyPool
4.95 out of 5 average rating, 262 reviewsDestinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Philadelphia Vacation rentals
- Washington Vacation rentals
- Boston Vacation rentals
- Ocean City Vacation rentals
- Pittsburgh Vacation rentals
- Niagara Falls Vacation rentals
- Jersey City Vacation rentals
- Portland Vacation rentals
- Newark Vacation rentals
- Baltimore Vacation rentals
- 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
- SoJo Spa Club
- Shawnee Mountain Ski Area





