Camp, Cabin Culture & Lodges: The Upstate New York Guide to the Best Spots for Group Trips & Gatherings

Hotel Lilien has the soul of a Victorian estate and the spirit of a modern dinner party. An 1890s estate redesigned by Field Theory and The Lost Boys Hospitality Group, it sits at the crest of Tannersville, minutes from Hunter Mountain and Kaaterskill Falls. Inside, original woodwork meets California cool: 18 rooms, a wood-paneled lounge, a stained-glass library, and enough vintage furniture to make even design editors take notes. 

Groups come together here for intimate weddings, brand events, or impromptu reunions that migrate from the lawn to the firepit, then back inside for brisket tacos and nightcaps. Every detail feels personal, from the antique glassware to the sleds waiting outside when the first snow falls.

Perfect for: intimate weddings, creative retreats, or any celebration that calls for character and good lighting.
Don’t miss: late-night drinks by the wood-burning stove and the house’s baked-to-order campfire cookies.

Is this a safe space to admit I’d host my birthday here and pretend it’s my own estate? With sixteen guest rooms, sweeping gardens, and a rooftop deck overlooking Windham Mountain, The Henson was designed for celebrations that merge intimacy with polish. 

The restaurant, Matilda, led by Jeremiah Stone and Fabián von Hauske Valtierra of New York’s Contra and Wildair, makes hosting feel easy; imagine delectable ruby red prawns, dauphine potatoes, and natural wine that keeps the table talking. Weddings assume the lawns; brand retreats fill the library, wellness room, and private dining space; friends come up with a new excuse to stay long past checkout. Every corner, from the honor bar to the garden paths, feels hand-made for connection.

Perfect for: culinary-forward weddings, private buyouts, and creative retreats with city-level service.
Don’t miss: dinner at Matilda (psst, order the Chocolate Mousse) and an evening Porto by the fire in the skylit lounge.

Infrared lightroom, fully stocked Hunter Boots closet, and room for man’s best friend? Yes, this venue will earn you every hosting accolade. Nestled in the heart of the Catskills, Eastwind Oliverea Valley is where Scandinavian minimalism meets camp-style connection. With twenty-seven rooms, saunas, hammocks, and a pool framed by mountain views, the property is the perfect fit for full-weekend weddings, creative retreats, and long-overdue reunions. 

Dandelion, the on-site restaurant, celebrates conscious farming and international comfort food. With a smoked trout dip that’s to-die-for, shrimp tagliatelle, and drinks like Baby Bear (blackberry, thyme, honey lemon, pinch of salt) and Panther Kill (reposado tequila, pineapple, lime, pepper liqueur), your guests will be thanking you for the next five years, at least. Every element, from the Glasshouse event space to the meadow tent setup, is built for gathering.

Perfect for: weekend weddings, wellness retreats, and creative offsites that mix nature and design.
Don’t miss: a post-sauna cold plunge followed by a glass of red and s’mores by the fire.

Ever thought of adding “hiking with goats” to your group trip itinerary? Well, you can now. Hemlock Neversink is 230 acres of earthy luxury built for restoration and a little fun. Thirty-three Quaker-inspired rooms sit across a historic campus with an indoor pool, hot tub, steam and three barrel saunas, daily movement classes, and a full spa. Programming rotates from goat hikes and stargazing to fabric-dye, mosaic, and terrarium workshops, plus Sip and Swim movie nights at the pool. Bittersweet, the plant-forward restaurant, keeps everyone fueled from breakfast to sunset cocktails on the wraparound porch.

Perfect for: lakeside vow renewals with a supper after, friend-forward spa weekends, writer or founder retreats, cookbook-club getaways, and team resets where the brief is rest first, ideas second.
Don’t miss: a Day Pass to the spa, aerial yoga in the light-filled Movement Studio, a morning forest walk, and dinner at Bittersweet.

If your idea of a fall holiday involves falconry lessons, farm walks, and focaccia still warm from the oven, this is your spot. Wildflower Farms in Gardiner spans 140 acres of orchards, meadows, and Shawangunk Ridge views, with 65 freestanding cabins and cottages that make “sharing space” feel like an upgrade. Groups rotate between yoga in the fields, forest immersion sessions, pasta workshops at Maplehouse, and the cold plunge circuit at Thistle, the property’s wellness hub. Clay, the restaurant, turns farm-grown vegetables and local proteins into clever, comforting dishes paired with natural wines and sage-infused martinis. It’s a place built for connection, where everyone leaves with a new skill and a few inside jokes.

Perfect for: group getaways, wellness-forward weddings, and creative retreats with friends.
Don’t miss: falconry with Chaco, focaccia-making at Maplehouse, and a sage martini by the firepit.

I spy the coziest lodge (with its very own Book Club) that would make even Martha take notes. Scribner’s Catskill Lodge redefined mountain hospitality; thirty-eight rooms and eleven luxury cabins that balance good design with real comfort. 

The property spans twenty acres with a library, sauna, pool, and enough gathering spaces to keep everyone connected yet relaxed. Prospect, the on-site restaurant, serves Chef Alejandro Reyes Herrera’s locally inspired cooking, best enjoyed after a hike, a swim, or a group game of bocce on the lawn. The Rounds, perched higher up the hill, make for a perfect basecamp for small weddings or creative teams looking to recharge.

Perfect for: elevated offsites, milestone birthdays, and weekend weddings that mix leisure with style.
Don’t miss: sunset cocktails at Prospect and morning yoga on the Bluestone Patio.

Did someone say, “A-frames, saunas, and a poolside bar serving drinks from a vintage Citroën van?” Consider your next group trip handled. Callicoon Hills pairs the nostalgia of a 1905 boarding house with the energy of a modern resort, all spread across twenty-three acres of the Western Catskills. 

Guests can choose between cabins, ridge rooms, or creekside cottages, then spend their days hiking, sauna-hopping, or lounging by the pool with s’mores in hand. The Conover Club anchors the property with field-to-feast comfort food and cocktails, while Rise & Shine Coffee Shop and The Reel Bar keep the pace easy from morning to night.

Perfect for: full-property weddings, team retreats, and creative weekends that mix work and play.
Don’t miss: morning coffee from Rise & Shine and an evening hike through the hills followed by Chicken Pot Pie at Conover Club. (Not even grandma can host this well.

If you’ve ever wanted to disappear into the woods with your favorite people (but with guided stargazing and Japanese forest bathing) this is your moment. The Chatwal Lodge sits on the 18,000-acre Chapin Estate, where the all-inclusive setup covers everything from fly-fishing lessons and mornings on horseback to nightly s’mores by the lake. Fourteen suites, including elevated treehouses with firepits and soaking tubs, make group getaways feel both wild and well-appointed. Dinners at Rustic Grill feature Hudson Valley ingredients like duck breast with blackberry dumplings and halibut with tomato ceviche, while the bar turns out clever classics (the Maple Old Fashioned deserves its reputation). Between croquet, forest trails, and farmers markets, it’s as close to adult summer camp as luxury travel gets.

Perfect for: friend reunions, all-inclusive weddings, and restorative weekends that mix nature with polish.
Don’t miss: treehouse cocktails by the lake and a fireside tasting menu at Rustic Grill.

If glamping had a publicist, it would be AutoCamp. This 37-acre property in the Hudson Valley is where design-savvy groups trade boardrooms and banquet halls for Airstreams, modern cabins, and fire pits under the pines. The clubhouse anchors the experience with happy-hour cider bars, local wine tastings, and game nights that last until someone breaks out the guitar. Weddings here skew refined-bohemian (dinner under string lights and toasts beside vintage Airstreams) while off-sites take a more creative route with watercolor workshops, guided forest bathing, or reiki sessions in the meadow. Make sure to pencil in a visit to their animal sanctuary, candlemaking class, and a Tortoise & the Hare lemon-mint cocktail at sunset into the itinerary.

Perfect for: modern outdoor weddings, wellness retreats, and design-forward team getaways.
Don’t miss: the grill kits from The General Store and s’mores by the fire after Clubhouse happy hour.

Inness feels like a mix between a sexy farmhouse and your cool friend's chef kitchen that turned you into an Arch Digest subscriber at age eight. A 225-acre retreat in the Hudson Valley where design, landscape, and hospitality converge. Forty rooms, split between farmhouse suites and standalone cabins, offer privacy for wedding parties or group weekends, with shared spaces that encourage communion. 

Days extend across tennis courts, trails, pools, and a nine-hole course by King Collins, while the new spa and bathhouse set a higher bar for wellness escapes. The restaurant overlooks the property’s organic farm and serves seasonal cooking that defines the region. For events, the barn and surrounding meadows provide a setting that feels natural yet meticulously composed.

Perfect for: design-conscious celebrations and long weekends that mix leisure with intention.
Don’t miss: farm-to-table dinners at sunset and private yoga sessions with panoramic mountain views.

If you’ve ever wanted a weekend that feels like slipping into an artist’s sketchbook, Pocketbook Hudson delivers. Set inside an 1885 textile mill, this creative compound blends hotel, bathhouse, café, open-fire restaurant, and subterranean nightclub into one very magnetic gathering place. Rooms range from projector-equipped studios to lofted suites in the roof trusses, each with oversized windows and custom furnishings.

Ambos, the signature restaurant by Chef Norberto Piattoni, leans into Argentine heritage and fermentation-forward cooking: think scallop crudo with charred hot sauce, mushroom agnolotti with bismark, and a cocktail menu by Arley Marks that includes a Monmouth sea salt martini worth the trip alone. Between brunch, bathhouse rituals, art programming, and late nights in Ether, groups barely need to leave the building.

Perfect for: creative retreats, small weddings, celebratory weekends, and friends who want design, dining, and culture in one address.
Don’t miss: dinner at Ambos, a soak in the communal baths, and a nightcap two floors down at Ether.

If your whole friend group’s in need of a shared exhale, book a row of Piaule cabins and let the stillness do what no weekend in the city ever could: glass walls that slide open to the woods, heated tile floors, treetop rain showers, and modernist rooms layered with handcrafted furniture and vintage finds. Spa access is reserved for overnight guests, which means you can run a real circuit without crowds; hot pool, mineral plunge, sauna, steam, then a yoga or meditation session in the studio before massages or a sunset sound bath. Keep the pace restorative with forest-bathing walks, guided hikes with a photographer, Reiki sessions for two, and long tables at the hilltop restaurant where breakfast comes with mountain views as fog lifts over the ridge.

Perfect for: wellness-forward friend retreats, founders’ reset weekends, low-key birthdays that trade hoopla for actual recovery.
Don’t miss: the Sunset Sound Bath with Stephanie, Group Meditation & Tea with Beth Rennig, Lesse Sculpt & Restore facial, and a winter hike with a guide who doubles as your photographer.

Pack your bags and your appetite for campfire stories with a side of good design. Upstate New York proves that “camp” can be cultured, where cabins come with saunas, chef kitchens, massage menus, and martinis. Consider this your Camp VR field guide to the stylish side of gathering in the wild. Or at least, the Catskills version of wild.

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Your guide to turning fire season into fine dining. Think heritage flannel meets Baccarat sparkle, and cabins that make s’mores feel like a Michelin moment.