Family-friendly vacation rentals in Middletown

Pocono Chalet~HeatedPool~Sauna~Firepits~Fireplaces

This is a one of a kind LINDAL CEDAR HOME, with an open layout, 16 foot Cathedral ceilings with floor to ceiling windows. Perfect getaway for family outings or friends getting out of the city. Following attractions are nearby: Lakes Wallenpaupack Promised Land State Park Skytop Camelback Ski/tube Kalahari Indoor Water Park Mt. Airy Casino NO PROMS NO FRATS POOL opens mid April and closes mid Nov. All guests are required to accept host's lease agreement prior to check in. Pets need approval

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

Cozy LakeView Farm near NYC/Rt.80 & Del. Water Gap

Enjoy Fresh Air & Spacious Views on your retreat w/ a Private Lake, Trails, Fields & Streams throughout. Beauty and Wildlife abounds. Spread out in an open layout apartment. See Guidebook for Seasonal Fun! Escape Pocono traffic & enjoy the countryside. *Close to NYC/Rt 80 thru a Quaint Moravian VIL. Appalachian Trail access. *Animal Tour w/Petting incl. Great local Farms/Markets w/Fresh Food. Alpaca & Wolf Preserve nearby. Hiking nearby. Farm Store coming soon.*3-day all Holidays. 1 dog<40pd.

POOL, Game Room, Lakefront, Hot Tub, PickleBall

Olibear is your ultimate spring retreat—ideal for couples, families, or anyone seeking a lakefront escape. Nestled by the water, our home offers warm charm amid blooming Pocono landscapes. Just 5 minutes from Bushkill Falls, explore vibrant spring or relax by the indoor community pool, open weekends 12-4 PM Enjoy the private hot tub, paddle kayaks or canoes, explore vibrant trails, or relax by the firepit under the spring sky. Indoor pool open on weekends Claim your spring escape now!

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Enchanted Castle - Unique & Charming Getaway

Recently renovated unique Harry Potter inspired 4BR/2BA 1600sq ft castle themed home near Kalahari, Mt Airy Casino & Camelback! Enjoy a private fenced yard with Hot Tub, Sauna, Fire Pit, Mini Golf, Swing Set, Patio & BBQ Grill. Inside: Pool Table, Ping-Pong, Chess, Scavenger hunt, Smart TVs, WiFi, Netflix & Family Games. Perfect Poconos getaway with comfort & fun for all ages—very close to top attractions, skiing, waterparks & dining. Great for families, couples & group retreats.

Cozy House - Lovely Fairytale TreeHouse - Hot Tub

Experience a nature lover's paradise in this stunning house with serene surroundings for play and relaxation. Perfect for families, it sleeps up to 6 adults and features a spacious living room, entertainment loft, and a 7-person hot tub for post-exploration relaxation. With its prime location, you're close to major Pocono Mountains attractions like Camelback Water Parks, Crossing Outlets, Delaware Water Gap, and more—the ultimate destination to explore this scenic region.

Peaceful Cabins by the river, excellent wifi!

Just figured out availability for our cabins this summer! The Big Cabin, located 15 feet from the water’s edge, will easily sleep six. The Little Cabin, 30 yards from the House with a water view and plenty of privacy, is perfect for a couple. Located on a secluded, non-thoroughfare road, it includes access to a private swimming hole and waterfall. Near the Shawangunk climbing mountain and hiking/cycling trails, Accord “downtown” and super chic Inness.

Serenity Retreat: Mountains, Waterfalls, Comfort

Enjoy a tranquil retreat overlooking a peaceful creek, set against gorgeous mountain views and nearby spectacular waterfalls. Just a short drive from Woodstock and Saugerties, NY this home on a serene country lane is a gateway to nature's beauty. With close proximity to local attractions, a lush garden, stunning mountain vistas, and a family-and-pet-friendly yard featuring a fire pit and bad mitten, it's the perfect blend of comfort and adventure.