Kid-friendly vacation rentals in Sheffield

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Sheffield

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

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Guest favourite

Cabin in Saugerties

4.86 out of 5 average rating, 176 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

Apartment in Saugerties

5 out of 5 average rating, 3 reviews

Esopus Creekfront I Family I Fire Pit I Kayaks

Welcome to Upstate Waterfronts! Whether you're traveling for the Holidays, visiting family, or looking for a restorative Upstate getaway - this Creekside gem has you covered. - 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

Superhost

Cottage in Hudson

4.84 out of 5 average rating, 128 reviews

Peaceful waterfront getaway (5 mi from Hudson, NY)

Love nature? Enjoy your own entire home on the Stockport Creek with private kayak/boat launch to the Hudson River. Hiking and bike trails nearby. You are immersed in Columbia County’s rural beauty between the Berkshires and the Catskills with Hudson’s hopping food and art scene minutes away. OMI sculpture park, Olana, farm markets, and Warren Street are a short drive. Ski Hunter or Catamount. Cozy wood burning stove as well as outdoor fire pit. Minimum 3 day stay. Ask about long term rates

Superhost

Home in Cornwall

4.82 out of 5 average rating, 93 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

Guest favourite

Home in Round Top

4.96 out of 5 average rating, 191 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.

Guest favourite

Home in Lake Katrine

4.95 out of 5 average rating, 110 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 favourite

Home in Athens

4.93 out of 5 average rating, 114 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.

Superhost

Home in Kingston

4.93 out of 5 average rating, 121 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.

Guest favourite

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

Superhost

Home in Saugerties

4.92 out of 5 average rating, 261 reviews

Mountainside Retreat-fully stocked

Welcome to Clove Cottage. A quiet get away in the middle of the woods near state land, hiking, streams & waterfalls. For those seeking nature, wildlife & viewing of the stars at night. Small get togethers are welcomed with pre-approval. Rental includes use of the cottage, converted barn, charcoal grill, fire pit and hot tub. Firewood is supplied. Host is always available and right down the road. Please no parties. This property is meant to be used as a peaceful mountain side retreat.

Guest favourite

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!

Guest favourite

Home in Athens

4.99 out of 5 average rating, 68 reviews

Lake House with Game Room

Relax with the whole family at this peaceful place. As a guest you'll have access to our Sleepy Hollow Lake community beach area, pools and playgrounds, and pickle-ball, tennis and basketball courts. Athens hosts a gourmet bakery, restaurants and an award-winning brewery. Drive 7 miles to explore historic Catskill, 12 to hip Hudson and for year-round sports enthusiasts - only 30 to Windham and Hunter Mountains. Game room with pool table, shuffleboard and bowling!