20 Family-Friendly Airbnbs in Upstate New York

From renovated train cabooses to secluded mountain retreats

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Vacations are wonderful…unless you have bored children who are complaining and wreaking havoc on what was intended to be a relaxing retreat. Fortunately, our roundup of the most family-friendly Airbnbs in Upstate New York has got you covered with numerous rental suggestions that have everything you need to keep your brood entertained without even leaving the premises. From private playgrounds and petting zoos on-site to basement game rooms and zip-lines in the backyard, there’s something for the whole fam (including rentals with baby items on-hand, like cribs and highchairs). Read on and start planning an escape from the big city that the whole family will enjoy.

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1. Revitalized 1902 Train Depot and Caboose in Accord, NY

  • 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: $500/night
  • Why We Love It: inground pool, pizza oven, projector TV, fire pit

Here, an enormous 19th century dairy barn with an interior so beautifully decorated (think: stained glass windows, antique clawfoot tubs and a stunning chandelier) that it deserves a spread in Architectural Digest. Indeed, the Woodstock Barn House is a swoon-worthy place to have a wedding and large enough for a family reunion, too. Little ones will love the farm animals, which can be visited at any time, and there’s an inground pool on the sprawling grounds as well. If you can tear yourself away from the property, be sure to check out the local swimming hole that’s just 200 yards away or drive two miles for a stroll through Woodstock’s charming town center.

3. Le Chalet in Prattsville, NY

  • 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.

4. Rose Hill Cottage in Coxsackie, NY

  • 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.

5. Sleepy Hollow Lake Resort in Athens, NY

  • 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.

6. Secluded Post-and-Beam Retreat in Ancram, NY

  • 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: 16+
  • Rate: $330/night
  • Why We Love It: nearby hiking trails, farm animals on site, architectural design

This charming 12-acre farm offers families a unique and comfortable glamping experience that’s perfect for folks who want to enjoy the outdoors with kids in tow. There’s a full outdoor kitchen and hot showers in addition to the geo dome, which is a lot nicer (and roomier) than a tent. Guests also have access to the many farm animals on the property, as well as the beautiful vegetable garden and numerous nature trails. The only thing to note is that you’ll need to bring your own air mattresses and bedding for any members of the group who won’t fit in the dome’s one full bed.

8. Killer Cat Mountain House in Hunter, NY

  • 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.

9. The Bird's Nest in Saugerties, NY

  • 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.

10. Private Modern/Rustic Apartment in Woodstock, NY

  • 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: 14
  • Rate: $808/night
  • Why We Love It: pickleball court, pool, swing set, game room

Gym, massage chair, chef’s kitchen—there are certainly enough luxe indoor amenities to make any grown-up swoon at this rental. But what about the kids, you ask? Oh, don’t worry…the pickleball court, ping pong table, swing set, game room and inground pool should provide them with plenty of ways to stay entertained while you roam the grounds, soak in the hot tub or enjoy the well-appointed interior.

  • Sleeps: 8
  • Rate: $450/night
  • Why We Love It: tree house, pool, ideal for large families

This A-frame log home sits on five secluded acres in the beautiful Catskill mountains and is spacious enough to comfortably accommodate the whole Brady Bunch. The place also has a playroom that’s stocked with children’s books and toys, and boasts both a private outdoor pool and hot tub. The property’s standout feature, though, is a pirate ship treehouse that’s certain to inspire oohs and aahs from all members of the brood. Oh, and if you’re traveling with a really little one, you can leave the gear behind, as this rental has a crib, high chair and pack n’ play available to guests.

  • Sleeps: 16+
  • Rate: $606/night
  • Why We Love It: game room, movie theater, pool

If you’re planning a whole family reunion, this palatial estate has certainly got you covered. There’s an inground pool, a 12-person hot tub, a movie theater that seats 16, a game room, a playroom, an outdoor playground and even a top-notch restaurant (run by the owners) that will deliver you prepared meals whenever you please. We could prattle on about the luxurious (and kid-friendly) accommodations, but instead we’ll let one reviewer sum it up: “five stars is not enough.”

  • Sleeps: 8
  • Rate: $214/night
  • Why We Love It: game room, fire pit, pool

This newly renovated A-frame in the Finger Lakes boasts a well-decorated, modern interior that, by all accounts, is very well-equipped with every amenity a family could need. There’s also a heated inground pool, an arcade room and a sprawling backyard with a fire pit that’s just right for making (you guessed it) s’mores.

15. Dingley Dell Estate II in Windham, NY

  • 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: 5
  • Rate: $565/night
  • Why We Love It: private swimming hole, waterfall, wildlife viewing, outdoor activities

Families will love the expansive and well-manicured lawns and convenient location (within walking distance of downtown Woodstock) at this property. There’s also a pool, a private waterfall, multiple swim holes and a pond that’s not for swimming, but is darn pretty. The property is surrounded by nature preserves, making for a very private and bucolic stay. As for the interior, it’s well-stocked with practical kid items and games. Plus, the design is to die for.

17. Bugg Haus in Freehold, NY

  • 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.

  • Sleeps: 4
  • Rate: $866/night
  • Why We Love It: architectural design, natural attractions, nearby towns

This architectural gem serves up a truly unique experience that feels like stepping into a work of art. The seven-acre property is situated on rock-walled land that features prehistoric boulders; it’s also conveniently located just outside the Mohonk Nature Preserve where families can enjoy all manner of outdoor activities. And when you return from your day of hiking and enjoying the Great Outdoors, you can occupy the kids with the many toys and books available while you whip up dinner in the gorgeous, glass-vaulted chef’s kitchen.

  • Sleeps: 4
  • Rate: $315/night
  • Why We Love It: cozy, fire pit, expansive yard

Dubbed the “coolest A-frame in NY” by the New York Post, this Kerhonkson rental, a 1961 cabin, offers a cozy and comfortable stay that’s just right for a family of four who want to enjoy the outdoors without leaving behind the modern comforts of home. The property boasts a fully renovated chef’s kitchen, an expansive yard surrounded by woods where kids can romp around and explore, plus board games and a TV for when you’re ready to unwind in the well-appointed interior. If you’re looking for a comfy, budget-friendly place to escape the city with kids, this property fits the bill.

  • Sleeps: 6
  • Rate: $297/night
  • Why We Love It: fire pit, yoga studio, lake access, nearby restaurants and shops

This recently renovated and quite stunning home looks like a treehouse—it’s elevated and surrounded by green, after all—but that description wouldn’t do it justice. Enjoy the gorgeous mountain views from the sprawling deck and floor to ceiling glass windows, have a family dance party in the yoga studio and be sure to avail yourself of the private access to five acres of land before retiring to a clean and modern living space. Oh, and don’t forget to reserve at least one afternoon to explore some of the top-notch restaurants and boutiques that are just 15 minutes away in the charming town of Livingston Manor.

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Freelance PureWow Editor

Emma Singer is a freelance contributing editor and writer at PureWow who has over 7 years of professional proofreading, copyediting and writing experience. At PureWow, she covers...

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