20 Family-Friendly Airbnbs in Upstate New York

• Sleeps: 8
• Rate: $610/night
• Why We Love It: train-themed, fire pit, great location

It doesn’t get much cooler than this modern reimagining of a historic early 20th century train depot, which boasts a sprawling and fully fenced backyard, a grand piano (for your budding Mozart), a popcorn maker, a reading nook with children’s toys and books, super neat capsule-style beds for the little ones (inspired by train sleeper cars), a sprung-floor dance studio and a separate caboose. Oh and did we mention hammocks, a fire pit and a prime location just off Main Street? All that aside, we fell in love with this place as soon as we saw the impeccable interior design, which is so brightly colored and fun it makes a Children’s Museum seem like a snoozefest. All aboard, indeed!

• Sleeps: 10
• Rate: $752/night
• Why We Love It: game room, gorgeous views, great location

Tots and teens alike will feel right at home in this pristine chalet—a mountain retreat that features separate lounge and play areas designed for both age groups, plus a game room (foosball!) and a fireplace. Outdoors, you’ll find a 10-acre lawn, two well-appointed outdoor decks and a hot tub, to boot—all of which boast stellar mountain views. We wouldn’t blame you if you decided to stay on the premises, but it’s worth noting that it’s a mere 10 to 15 minute drive to Windham and Hunter, where outdoor recreation opportunities abound all year long. (Think: skiing, snow tubing, hiking and ziplining.) Bottom line: Family-friendly comfort awaits at this homebase, no matter what your itinerary has in store.

• Sleeps: 10
• Rate: $1,115/night
• Why We Love It: pool, games area, gorgeous views

Don’t be fooled by the name, ‘cause this is no cottage. In fact, it’s a stately mansion that sits on 30 acres of meticulously groomed land and provides guest access to a (seasonal) saltwater pool and separate, kid-friendly barn that’s well-equipped with everything from board games, as well as teen attractions like pool, darts and ping pong. (There’s a very large TV, too.) Plus, the homey, coastal-meets-farmhouse decor and scenic Hudson River views aren’t half bad, either.

• Sleeps: 14
• Rate: $800/night
• Why We Love It: water sports, outdoor activities, multiple TVs

This lakefront gem promises to keep the whole family occupied with an array of water activities—there are kayaks, canoes, paddle boats, fishing poles and more—but when it’s time to return to dry land, the kids can also avail themselves of numerous resort amenities, including tennis, pickleball and basketball courts, as well as a golf range, sandy beaches and multiple parks and trails. As for indoor entertainment, there are a whopping six smart TVs and a ping pong table, to boot. Let’s just say you won’t be hearing ‘I’m bored’ on this family vacation.

• Sleeps: 6
• Rate: $205/night
• Why We Love It: outdoor activities, treehouse with zipline, gorgeous views

Books, toys and games fill this charming retreat, which is situated on seven secluded acres of open fields, manicured lawns and forest, and located just a stone’s throw away from a host of outdoor activities (hiking, skiing, tennis, golf and lake swimming, to name a few). Best of all, there’s a well-equipped treehouse and a zip line where kids can play while the grown-ups plan the daily itinerary, or just chill out for a few. Plus, this package deal also includes breathtaking views, beautiful natural surroundings and a whole bunch of wildlife—so you really can’t go wrong.

• Sleeps: 10
• Rate: $441/night
• Why We Love It: gorgeous views, games room, great location

You’ll swoon over the floor-to-ceiling glass doors, the deck with stunning mountain views and the Parisian-chic designer furnishings. And fortunately, you’ll have enough time to savor it all like a glass of fine wine (have one of those!) while the kids entertain themselves with some good old fashioned gaming in the basement, where a Pacman arcade machine, a Marvel digital pinball machine, a classic Nintendo entertainment system and a whole host of classic board games can be found. Yep, this combination of competition and relaxation is a winning one indeed.

• Sleeps: 4
• Rate: $224/night
• Why We Love It: animals on property, popcorn machine, trampoline

It’s hard to pick a best feature of this spacious, kid-friendly and impeccably farm stay home…but if you are vacationing with little ones in tow, it’ll probably be a toss-up between the children’s play set, the trampoline, and the collection of rescue animals, which is so extensive it could give a city zoo a run for its money. (There are emus, pigs, donkeys, horses, rabbits, spotted deer, geese, roosters and hens!) Then again, water-loving members of your brood might be partial to the private stream, three foot swimming hole and cascading waterfall. However you keep them busy—and it won’t be hard—just make sure that at least one person is napping in a hammock at any given time and the popcorn machine is always ready to dispense a snack.

• Sleeps: 4
• Rate: $189/night
• Why We Love It: playground, gorgeous views, great location

This budget-friendly booking boasts amazing mountain and river views—best enjoyed from the generously-sized private deck over dinner al fresco—and plenty of rustic charm. There’s also a private playground that guests can access freely and a stream just steps away for splashing and exploring. What’s more, this five-star rental is also located within walking distance from the many acclaimed restaurants and quaint shops that Woodstock has to offer, so there’s really something for everyone.

• Sleeps: 12
• Rate: $570/night
• Why We Love It: entertainment room, playground, outdoor games

This large, refurbished Windham estate has a movie theater/entertainment room with a generously-sized 85-inch TV and surround sound…but we’re guessing it won’t be too hard to stick to screetime limits, since there’s also a huge, lush lawn, a private playground and swing set, a volleyball net and a set-up for both basketball and badminton. In other words, you don’t even have to leave the property to find a whole bunch of energy-burning, kid-friendly recreation opportunities. (And that means the grown-ups can kick back and take in the mountain views from the comfort of a patio lounge chair.)

• Sleeps: 16+
• Rate: $1,750/night
• Why We Love It: 7 bedrooms, outdoor activities, hot tub

Looking for a home that will accommodate multiple families? Here it is. This palatial estate in Freehold, NY sits on a sprawling 15-acre property, featuring a horseshoe pit, nature trails and a whole lot of land to explore. (Scavenger hunt, anyone?) The house also has a wide selection of oversized yard games on offer, an outdoor movie projector screen and hot tub. Given its proximity to Hunter and Windham mountain, it’s safe to say that winter sports are another big draw—but it’s worth mentioning that the Bugg Haus is also conveniently located within easy reach of of kid-friendly attractions, including waterparks, ziplining adventures and other warm weather activities.