Kid-friendly vacation rentals in Stockbridge

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Stockbridge

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

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Guest favorite

A wooden deck is shown featuring a large umbrella providing shade over a seating area. A patterned rug lies on the floor, accompanied by a potted plant. Two lounge chairs and a small table create a comfortable outdoor space, surrounded by lush greenery.

Cabin in Saugerties

4.87 out of 5 average rating, 183 reviews

Private Woodstock Getaway w Hot Tub

Relax in this cozy retreat on a private road. Snuggle up by the fire, play some records, relax on the sunny deck, or jump in the hot tub. Cook dinner in the fully stocked kitchen or grill on the deck and enjoy your meal in the screened in porch. The master bedroom has a king-size bed and quality linens, as do the other two bedrooms, one with a queen and one with 2 twins beds. Relax downstairs in the family room, watch a movie, or cozy up by the wood burning stove. Short drive to the town of Woodstock ! Close to skiing, hiking & swim holes! $50 extra for dogs. No cats. Use hot tub at your own risk. The whole home is yours except the garage remains closed. Always available if any issues arise, but not on the property. The house is set back on a private road. It's a genuine retreat, but still only a short drive from the shops and restaurants of Woodstock and Saugerties. Local hikes abound, and venture a little further to find swimming holes and skiing. If you have a small child, I suggest bringing a gate as there are stairs to the basement.

Superhost

A spacious living area features a large, soft sofa with decorative pillows, facing a rustic coffee table. Natural light fills the room through multiple windows, with a dining table set for six in the background. Soft, neutral tones create a serene atmosphere.

Home in Cornwall

4.82 out of 5 average rating, 95 reviews

State Forest Getaway

Enjoy our Mountain getaway for year round fun! There are lots of activities close by-Mohawk Ski Mountain, Indian Lake and historic Covered Bridges! Hike in the backyard, cool off in the creek or relax in front of the Wood-burning fireplace or get the whole family together for a fun BBQ on the outdoor deck. We have 4 comfortable bedrooms plus daybed room and 3 bathrooms and a fully equipped Chefs Kitchen. The living room is great for lounging and perfect a movie night watched on the projector

Top guest favorite

Home in Round Top

4.96 out of 5 average rating, 195 reviews

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.

Top guest favorite

An enclosed porch features two metal-framed chairs with cushions, positioned near a small table. A decorative rug with vibrant floral patterns covers the floor. A potted plant and a lantern add to the decor, with sunlight streaming through the windows overlooking the water.

Home in Lake Katrine

4.95 out of 5 average rating, 111 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Guest favorite

Home in Athens

4.92 out of 5 average rating, 118 reviews

Lake house, 700 ft waterfront - from every room

Panoramic views from the wrap-around deck offers privacy and 700 feet of lake frontage from this comfortable home. Enjoy the sunrise and sunsets views of the lake from EVERY room. Two kayaks, canoe, paddle board to be enjoyed from its private beach. The great room has full lake view, heated floors and two large decks. This home offers 4 bedrooms, 2 and 1/2 baths, a finished lower level that features game room with private deck, ping pong table, giant Jenga, home gym, and large 55in TV.

Guest favorite

A wooden playset is situated in a shaded area, featuring a slide, climbing wall, and swings. Nearby, a grassy space with pebbled pathways leads to a rustic barn surrounded by trees. Natural light filters through the forest canopy, creating a serene atmosphere.

Home in Saugerties

5 out of 5 average rating, 149 reviews

Upstate Modern Scandinavian Barn in the Catskills

Renovated 1850's barn with 3 bedrooms and an ample loft space that can serve as a fourth. The house also has a large rec room with cathedral ceiling buttressed by hand-hewn beams, well-equipped kitchen, Scandinavian wood stove, sauna, home gym, and projector. Outside: 2 private decks with amazing views of Overlook Mountain, private grill, private hot tub. On property: shared tennis court, swing set, fishing pond, heated pool (summer only). 2 hours from NYC, 10 min. to Woodstock & Saugerties.

Superhost

A designated workspace is visible, featuring a wooden desk with a monitor and a sleek chair, positioned against a gray wall. A cozy living area can be seen through the open doorway, with a comfortable blue sofa and a decorative table, offering an inviting atmosphere.

Home in Kingston

4.93 out of 5 average rating, 132 reviews

Hightop House: Modern, Uptown, Centrally Located

Hightop House is a newly renovated Victorian home in midtown Kingston. Ideal for a WFH getaway (inhouse and coworking partnership), groups, and families. Enjoy easy access to Kingston and surrounding areas. 3 bedrooms, 2.5 baths. Large open kitchen, contemporary furnishings, brand new appliances. Walk to UPAC / Stockade District, Keegan Ales. <10 min drive to the Rondout district, Hutton Brickyards. 10min to Ashokan Rail Trail, Onteora Lake. 20min drive to Saugerties, Woodstock, Rosendale.

Superhost

A brick fireplace serves as a focal point, with several white candles arranged on the hearth. Natural light filters through a nearby window adorned with sheer curtains, illuminating the seating area with cozy cushions beside a built-in bookshelf.

Apartment in Kingston

4.77 out of 5 average rating, 115 reviews

In the Heart of Kingston

Pet friendly. A comfortable apartment in the heart of midtown Kingston. Enjoy a cup of coffee in the garden, or curl up with a book in the window seat in the living room. This apartment is a great spot to relax from a day of exploring Kingston. You will be close to everything when you stay at this centrally-located place. Note: located near a train; so if you are a light sleeper, it might not be a good fit. Garden area is still in winter mode (until May 15th), so please excuse the mess.

Guest favorite

The living room features light green walls with large windows allowing natural light to fill the space. A patterned sofa and two armchairs offer seating. A coffee table sits on a layered area rug, while a corner with a small table and a chair adds functionality.

Home in Athens

4.84 out of 5 average rating, 170 reviews

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

Guest favorite

Bungalow in Great Barrington

4.91 out of 5 average rating, 117 reviews

Idyllic Berkshires Getaway

Secluded large ranch in the country on 8 acres with pastoral scenic views, only 7 minutes drive from the center of Great Barrington and Lake Mansfield Beach, 10 minutes to Ski Butternut, 12 minutes to Stockbridge, 20 minutes to Lenox and Tanglewood . Kids playroom and a spectacular jungle gym, perfect for entertaining inside by the fire or outside on the patio with the bbq with beautiful views surrounded by pine trees. Perfect for fall foliage, skiing, spring and summer!

Superhost

An arcade system is displayed, featuring a vibrant control panel adorned with classic ghost characters. A television mounted above showcases various game options, while a nearby list of available games provides additional details. A simple chair completes the gaming setup.

Apartment in Saugerties

5 out of 5 average rating, 3 reviews

Creekfront I Hot Tub I Sauna I Fire Pit I Kayaks

Welcome to Upstate Waterfronts! Looking for a restorative Upstate getaway? This Creekside gem has you covered. - HOT TUB - SAUNA - 3 bedrooms/ 1 full bathroom - Fully equipped kitchen & high-end amenities - Private creek access - including kayaks/vests/paddles - Stunning creek views - including a water facing balcony - 3,000 Arcade games, 75'' Smart TV, endless board games - High-speed WiFi - Prime location - walkable to town/restaurants/shops/beach

Guest favorite

A scenic view from a wooden deck showcases rolling green hills and tall trees. A tranquil pathway winds through the landscape, leading to nearby homes. Gentle sunlight filters through the foliage, enhancing the natural beauty of the surrounding area.

Home in Palenville

4.96 out of 5 average rating, 163 reviews

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.