Looking for Cool Hotels in Upstate New York? Look No Further

Are you searching for a cool hotel in upstate New York? Are you looking for something different from the same old hotel experience? We’ve got just the thing you’re looking for. Located in the heart of the Catskill Mountains, Calicoon Hills is your antidote to the ordinary. Offering hiking trails, fishing, and other outdoor activities, you’re bound to find something you love here.

A Boutique Resort in the Catskills

The heart of this cool hotel in upstate New York is the Boarding House, which can trace its roots to 1905. Today, Calicoon Hills has expanded to 23 acres of luxury, featuring a pool house, ridge rooms, and numerous cabins.

The vibe at Callicoon Hills is “adult summer camp”, in the best way possible. You’re surrounded by wilderness, hanging out with friends, and having s’mores every night (they’re complimentary!), but everything is elevated. Instead of bunk rooms, you’ll be staying in luxurious private rooms. Instead of chugging juice in the mess hall, you’ll be sipping cocktails at the resort’s exclusive restaurant. There’s no itinerary, no obligation. You’re free to make matching T-shirts if you’d like, though. We won’t judge.

Cozy Catskills Cabins

The most iconic accommodations at Callicoon Hills are the eleven A-frame cabins. These tiny cabins each feature a queen-size bed and floor-to-ceiling windows, offering stunning views of the Catskills wilderness. The overall effect is like sleeping in a spacious tent, but with modern comforts. There are a lot of cool hotels in upstate New York, but these A-frames take the cake.

The cabins share a communal bathhouse with seven full bathrooms, each equipped with a rain shower. These aren’t your standard campsite bathrooms with shared showers and public toilets. They’re fully appointed, spa-like bathrooms.

The cabins additionally share two communal fire pits, where guests can gather every night for complimentary s’mores. You also have easy access to the resort’s walking trails, which are lit with twinkling lights for optimal ambiance.

“I Asked for a Cool Hotel in Upstate New York, Not a Campsite!”

Perhaps glamping isn’t your thing. No problem; Calicoon Hills offers so much more than glamping. As mentioned before, the heart of the hotel is the Boarding House. This stately manor house features rooms with king- and queen-sized beds, decorated with hardwood floors and locally made details.

The largest rooms are the King suites, located on the third floor, which offer ample space for relaxation and comfort. The other rooms vary in size but feature en-suite bathrooms, sound machines, and a chic, bed-and-breakfast vibe.

The Boarding House is home to Callicoon Hills’ restaurant, Conover Club. Here, you can get brunch, dinner, and cocktails, with ingredients sourced from local farms and breweries. The menu varies by season but features comfort food staples, including burgers, fried chicken, steak, and pasta. It’s the perfect place to relax, surrounded by friends, while indulging in some of the best food the Catskill Mountains have to offer.

For a quick bite, the boarding house also features the Rise and Shine Cafe, which specializes in bagels and coffee. Like Conover Club, everything is sourced from the surrounding regions. The coffee is from Brooklyn, and the bagels are from a shop in Roscoe, NY. The commitment to highlighting local businesses is one of the coolest things about this upstate New York hotel. They really embrace their identity as an independent resort and go out of their way to showcase other independent businesses. In a world where even experiences are mass-produced, this is a refreshing change of pace.

The Pool House and Ridge Rooms

If the A-frames are an elevated campground and the Boarding House is a chic bed and breakfast, then the Pool House and Ridge Rooms are a luxe take on a motel. These are exterior-facing rooms, many of which are accessible, and are just as well-appointed as their counterparts in the Boarding House.

The Pool House is, as the name implies, next to the resort’s pool. This creek-fed pool is one of Calicoon Hills’ few concessions to the Catskills tourism culture, with plenty of lounge chairs and a modified Citroen serving food and drinks. There’s an unquestionably casual, neighborhood atmosphere here. People are talking to one another, relaxing, and sipping on local brews. Even the Citroen has the vibe of a snack bar or ice cream truck. Well, if ice cream trucks served IPAs, anyway.

The Ridge Rooms are situated on the western edge of the property and consist of three single-story buildings, each named for the view it offers: Hill House, Tree House, and Lake House. Each building offers stunning views of the surrounding landscape, along with all the amenities of the Boarding and Lake Houses. These cozy rooms have easy access to the walking trails, along with firepits and, of course, s’mores.

The Creekside Cabin and Haypress Barn

The last accommodation at Callicoon Hills is located a fair distance from the main property, but it is by far the most spacious. The Creekside Cabin comes complete with a craftsman kitchen, a clawfoot tub, and enough beds to sleep six. There’s also a cabinet filled with board games, plenty of cozy nooks, and the only television you’ll find in the guest accommodations.

The cabin is located near the Haypress Barn: Callicoon Hills’ largest indoor event space. It’s a popular wedding destination, which is why a stay at Creekside is included in The Hills’ most extensive wedding package. The Haypress Barn is a rustic, multi-tiered space perfect for wedding receptions, complete with a deck and fire pit. Because yes, there are s’mores. You gotta have s’mores.

The Coolest Hotel Amenities in Upstate New York

Accommodations are only half the story, which is why Callicoon Hills offers some truly exquisite amenities. We’ve already mentioned a few, such as the pool and complimentary s’mores, but there’s a lot more that the Hills have to offer.

Callicoon Hills is situated on 23 acres of Catskills beauty, providing guests with ample space to spread out and explore. Here, you’ll find forest trails lit at night by twinkling lights, bubbling creeks, and a landscape more photogenic than you can imagine. If you’re a city dweller looking for some peace and quiet, Callicoon Hills will feel like a revelation.

It’s not all relaxing on hammocks and roasting marshmallows, however. Guests seeking to adopt a healthy routine can work out at the indoor-outdoor gym, complete with an elevated yoga deck that overlooks the Catskills’ picturesque hills and valleys. Afterward, you can destress in the barrel-style sauna, and let the stress of city life melt away.

Beyond The Hills

Outside the bounds of the resort, there’s plenty to do in the Catskill Mountains. From hiking and horseback rides to the site of the world’s most famous music festival, here’s an overview of the attractions you’ll find near Calicoon Hills.

If you’re a fan of the outdoors, you’ll want to stop at one of the many parks around the area, such as the historic Tusten Mountain, the hiking trails of Jensen Ledges, or the biking trails of Crystal Lake. Depending on the season, you’ll find everything from horseback riding and archery to skiing and ice fishing. Oh, and there’s plenty of golf. You gotta have golf.

One of the most interesting attractions in the Catskills is Bethel Woods: the site of the original Woodstock Music and Art Fair. Bethel Woods is part park, part museum, and part archaeological site. Here, you can walk through recreations of sites like the Bindy Bazaar, see artifacts from the festival, or even catch a live performance.

Cool Hotels in Upstate New York and Beyond

If Calicoon Hills appeals to you, you can find it and other out-of-the-ordinary experiences in Nook Outdoor’s curated catalog of boutique hotels and experiences. Whether you’re looking for an escape to the Catskills, a Hawaiian getaway, or a stroll through Texas Hill Country, we have some of the coolest places to stay in our collection. Browse what we have to offer, and book your next adventure today.