The Catskill Mountains of New York have been attracting stylish families since before it was officially “a thing.”
What used to be a quiet upstate New York getaway is now a favorite for style-minded families, with small shops, creative dining, modern cabins, and boutique hotels that genuinely live up to the hype.
If you’re dreaming up a Catskills vacation that feels fresh, inspiring, and totally doable with kids, this guide has you covered.
Here’s where to stay, where to explore, and where to eat in the Catskills when you want a getaway that checks both the style and family-friendly boxes.
The Best Towns for a Stylish Catskills Vacation
Every Catskills town has its own style… some lean artsy, some feel like curated design catalogs, and some are just beautifully historic and simple.
Find the Catskills town that matches your family’s style…
Woodstock, NY
Woodstock, NY is the “artsy cousin” in the Catskills… the kind of place where handmade trinkets, tie-dye displays, record shops, and design-forward boutiques sit side by side along Tinker Street.
Wander in and out of luxury design shops like Pacama Handmade or stop by quirky Candlestock if you want to show your kids the “dripping candle mountain”.
Woodstock, NY is creative, colorful, and one of the most walkable small towns in the Catskills.
Phoenicia, NY
Phoenicia, NY is small and laid-back with a retro-cool vibe that feels straight out of an old Catskills postcard.
The heart of town is basically a single stretch of Main Street with quirky shops, a classic hardware store, and that cozy, slightly lived-in Catskills charm.
Hunter, NY
Hunter, NY isn’t really a “downtown” in the traditional sense, it’s more of a mountain village built around Hunter Mountain.
The design appeal here comes from the modern lodges, A-frame rentals, and stylish stays that have popped up nearby, plus the mountain architecture that naturally gives everything a slightly Scandinavian feel.
Windham, NY
Windham, NY has a more of a town center than Hunter, especially along Main Street, where you’ll find a small but thoughtful cluster of shops, coffee spots, and restaurants.
It feels tidier and more put-together, with boutique hotels and stays that lean stylish without being overly curated.
Livingston Manor
Downtown Livingston Manor it’s more like a tiny stretch of Main Street with a few very thoughtfully designed spots sprinkled in.
Homestedt is a can’t miss a beautifully curated home + design shop, and The Walk In bakery has a warm Scandinavian vibe that makes you feel right at home.
Design-Forward Stays for Your Catskills Vacation
These are the places to stay in the Catskills when you want an elevated stay…
Restored lodges… creative boutique hotels… rentals with indoor pools… and modern cabins that make your Catskills Vacation feel cooler from the moment you arrive.
Eastwind Oliverea Valley
- Big Indian, NY
Eastwind Oliverea Valley in the Catskills has that modern-upstate New York vibe down to a science.
Scandinavian cabins, warm wood interiors, pretty views in every direction, and a laid-back atmosphere that instantly drops your shoulders a level.
It’s intentionally designed without feeling precious, and manages to be cozy, easy, and welcoming for families.
If bringing the dog is non-negotiable, our guide to the best pet friendly hotel rooms has plenty of options worth bookmarking.
Why Eastwind Oliverea Valley Works for Families
- Freestanding A-frame cabins + room layouts that feel comfortable, not cramped
- Peaceful property with outdoor spaces for kids to explore
- On-site restaurant (Dandelion) that saves you a drive to town
- You’re close to Phoenicia and kid-friendly hiking trails.
Urban Cowboy Lodge
- Big Indian, NY
Set in a restored 1800s alpine lodge, Urban Cowboy Lodge is what happens when Brooklyn aesthetic meets Catskills Mountain escape.
Expect gorgeous clawfoot tubs, wood-burning stoves, and floor-to-ceiling views in the guest suites.
It’s a bit more of a “vibe” than a kid-focused stay, but the easy hiking trails, and on-site restaurant make it surprisingly doable with older kids.
Why Urban Cowboy Lodge works for families:
- Design-forward lodge with 28 eclectic and thoughtfully designed rooms
- Riverside soaking tubs, vintage details, and bold interiors
- On-site restaurant and cocktail bar
- Near Slide Mountain and Peekamoose hiking trails
- Best for families with older kids
Hotel Kinsley
- Kingston, NY
Hotel Kinsley is Uptown Kingston’s collection of four beautifully restored buildings that feel cool without trying too hard.
The main address at 301 Wall Street is the heart of it all, with the restaurant, lobby, and that old-bank-vault bar you’ll want to peek into.
Rooms are spread across the nearby historic houses, all an easy walk to Wall Street’s boutiques, bakeries, and the kind of cafés where you can settle in.
Why Hotel Kinsley works for families
- Stylish rooms with vintage details, cozy extras, and easy downtown walkability
- On-site restaurant serves weekend brunch + weekday dinner
- Easy drive to Forsyth Nature Center or the Empire State Railway Museum
- Great for design-savvy parents and kids who love exploring a new town on foot
Scribner’s Catskill Lodge
- Hunter, NY
Scribner’s Catskill Lodge is a modern mountain lodge in the Catskill Mountains blending rustic charm with sleek, editorial design.
Rooms feature maple floors, Malm fireplaces, and private decks with mountain views.
It has that relaxed, stylish feel that makes a Catskills Vacation so easy to love, with firepits, board games, and a glass-walled restaurant made for unwinding after a day outside.
When you’re ready to branch out from the Catskills, our map of unique places to stay has dozens of cool finds you’ll want to book.
Why Scribner’s Catskill Lodge works for families:
- Design-forward lodge with 38 rooms and suites
- Private cabins (The Rounds) a short walk from the lodge for more space and privacy
- Seasonal outdoor pool, lawn games, and fire pits
- On-site restaurant (Prospect) with views and a locally sourced menu
- Easy access to skiing, snow tubing, and summer hiking trails
Kenoza Hall
- Kenoza Lake, NY
Once a 1900s boarding house, Kenoza Hall sits on 55 quiet acres along Kenoza Lake.
It’s the kind of Catskills vacation that naturally slows everyone down.
You can stay in the main inn or one of the lake-view Bungalows, which gives you more space, private porches, and a soaking tub you’ll use at least once.
The property has a pool, spa, lake access, walking trails, and a restaurant that works for everyone.
Why Kenoza Hall works for families:
- Spacious rooms and suites with a rustic magazine feel
- Lake-view Bungalows available for families who want space and privacy
- Seasonal outdoor pool and lake access for easy exploring
- On-site restaurant
- Short drive to farm stands, quiet towns and kid-friendly hikes
Callicoon Hills
- Callicoon, NY
With a mix of cabins, Ridge Rooms, and Boarding House stays, Callicoon Hills delivers a relaxed, design-forward Catskills setting without overdoing it.
The outdoor pool, sauna, and wide-open grounds give families room to play together.
Plus, you’ll love having the Rise & Shine Coffee Shop and the Conover Club easily on-site.
It’s the kind of Catskills vacation spot that balances style, space, and real-life ease.
Why Callicoon Hills works for families:
- Modern rooms and cabins across a stylish multi-building property
- Wide lawn, outdoor pool and open grounds with a laid-back vibe
- On-site café + restaurant
- Minutes from downtown Callicoon’s shops and weekend farmers market
Wylder Hotel Windham
- Windham, NY
Wylder Hotel Windham is made up of several restored buildings spread out along the river, giving the whole property a relaxed, small campus feel.
The rooms are bright and stylish, but the Catskills charm comes from the long porches, mountain views, and open spaces that make the place feel instantly welcoming.
If you’re aiming for stylish getaways that don’t overwhelm the budget, this list of affordable family vacation ideas is a great place to start.
Why Wylder Hotel Windham works for families:
- Bright, modern rooms and suites spread across a handful of restored historic buildings
- Riverfront grounds with open lawns and room to play
- On-site restaurant and bakery keep meals easy
- Minutes from Windham Mountain for year-round outdoor fun
Shandaken Inn
- Shandaken, NY
Originally built as the clubhouse for the old Rip Van Winkle Golf Course, Shandaken Inn has been reshaped into a clean, modern lodge with subtle nods to its 1920s roots.
This vacation stay in the Catskills mixes modern lines and historic charm on a 12 acres with direct access to the Esopus Creek.
It feels peaceful without being isolated, and it’s the kind of upstate getaway where you’ll naturally fall into a slower rhythm.
Why Shandaken Inn works for families:
- 15 individually designed rooms or 3 private cabin options
- 12-acre private property with mountain views and access to the Esopus Creek
- Seasonal pool, tennis court and space to play
- Quick drive to Phoenicia for dining and low key outings.
Private Windham Rental with Heated Indoor Pool
- Windham, NY
This 5-bedroom modern estate sits on 5 wooded acres in the Catskill Mountains and features the ultimate family amenity… a heated indoor salt-water swimming pool.
With mountain views, a fully equipped kitchen, wood-burning fireplaces, and a deck overlooking the slope at Windham Mountain, it feels like the stylish Catskills Vacation you’ve been looking for.
Why this rental works for families:
- Large modern house with 5 bedrooms that sleeps 12… perfect for two families or a group.
- Heated indoor pool, multiple fireplaces and open living spaces
- Minutes from Windham Mountain, local shops and easy dining spots
If your ideal getaway includes swimming year-round, our list of rentals with indoor pools near NYC is full of family hits.
Hunter Mountain Cabin with Indoor Pool
- Lanesville, NY
Why this rental works for families:
This Catskills cabin sits a few minutes from Hunter Mountain and has that easy, gather-everyone-together layout families love.
The heated indoor pool and sauna are the standout features… a total lifesaver on cold-weather trips.
With the ability to sleep 16+ guests in 8 bedrooms there’ll be plenty of space to spread out and enough bedrooms that no one gets stuck sleeping in the living room.
Why this rental works for families:
- Eight bedrooms with space for multiple families or a group
- Heated indoor pool, and sauna
- Stylish Catskills cabin that feels comfortable and not overdone
- Quick drive to Hunter Mountain and nearby lakes and trail heads
Cool Things to do in the Catskills That are Worth Your Time
From outdoor sculpture parks to artsy barns and walkable downtowns, these cool things to do in the Catskills add just the right amount of style and personality to your Catskills vacation.
Opus 40
- Saugerties, NY
Opus 40 is a one-of-a-kind 6.5-acre bluestone sculpture created inside 63 acres of trails, meadows, and historic buildings, and it’s one of the Catskills spots that actually lives up to the hype.
It’s open seasonally (April-November), with Thursday-Monday hours in peak season and weekends only in the shoulder months.
Plan for at least an hour to explore, pack a picnic, bring sunscreen and bug spray and know that dogs have to sit this one out.
Emerson Kaleidoscope
- Mount Tremper, NY
The self-proclaimed world’s largest kaleidoscope tucked inside an artsy converted barn. It’s quirky, colorful, and one of those quick stops everyone ends up talking about later.
Explore Tinker St.
- Woodstock, NY
Indie shops, galleries, bookstores, and cafés with personality… all along a walkable main street that feels both creative and easy with kids.
Rail Explorers
- Phoenicia, NY
Rail Explorers in the Catskills lets families ride open-air rail bikes along a quiet rail line, making the scenery the star of the show.
Rides are seasonal with timed departures, so plan ahead. It’s fun, outdoors, and way more fun than telling kids to take a walk.
Want to ride the rails in a totally different way? Check out our fall foliage train rides to add to your list.
Bethel Woods Center for the Arts
Even without a concert on the calendar, the museum and grounds are worth the trip. Modern architecture, open fields, and plenty of space for kids to roam while you soak in the views.
Catskill Mountain Railroad
- Kingston, NY
A classic train ride through the Catskill woods. Quick, scenic, and charming in a way that works for both little kids and the too-cool older ones.
Widow Jane Mine
- Rosendale, NY
The Widow Jane Mine is one of those unexpectedly cool Catskills stops… short trails to explore, a touch of history, and a 55-degree underground space that feels like a secret.
The 22-acre Snyder Estate is open seasonally April through summer, the museum opens on Sundays, and they ask for a $5 donation per person.
If planning a Catskills Vacation has sparked your wanderlust, Cold Spring, NY is another close, easy win.
Where to Eat in the Catskills
These restaurants in the Catskills fit the vibe perfectly… creative, relaxed, and easy to enjoy with kids in tow.
The Phoenicia Diner is a Catskills icon. Retro-modern diner design, big windows, a menu kids love, and menu specials you’ll secretly dream about until your next visit.
Silvia strikes that sweet spot of style, covered outdoor dining, and an open kitchen that’s basically built-in entertainment for kids.
The menu leans more date night, but the energy stays relaxed enough to bring the whole family.
Bread Alone is an easy stop right off Route 28 en route to Woodstock, NY.
It’s quick, relaxed, and exactly the kind of low-pressure café moment a Catskills trip needs.
Good Night in Woodstock, NY is colorful, bold, and super stylish…
Southeast Asian–inspired dishes served in a space that’s fun, warm, and memorable.
Westwind Orchard is a farm stop that feels both cool and kid-friendly.
Wood-oven pizzas, fresh pastas, house ciders, and a lawn that keeps everyone happy. It’s relaxed, stylish, and exactly the kind of low-effort win you want on a Catskills getaway.
Ready to Plan Your Catskills Vacation?
You’ll love vacationing in the Catskills because you’re never choosing between what looks good and what works for families… you get both.
Once you know where you’re staying, eating, and wandering, the rest is blissfully simple. And that’s really the whole point of a Catskills vacation.
Happy Travels…
