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A Guide to Callicoon, NY
Set along the banks of the Delaware River in Sullivan County, Callicoon blends river-town roots with a creative, slow-living spirit. Once a railroad and farming hub, the town has quietly evolved into one of the Western Catskills’ most inviting pockets — with vintage shops, natural wine bars, and farmers markets tucked between rolling hills and forested trails.
A Guide to Hudson, NY
Hudson, NY is the perfect town for your maiden voyage upstate — in fact, it was ours! This once "sleepy town" now brands itself the "downtown of Upstate" with 200 independent establishments including antique and boutique shops, hotels, art galleries, restaurants and bars, mostly along Warren Street. Visually, this charming town is a treat, delighting visitors and aesthetes with its stunning and Wes Anderson-esque architecture. The restoration of some 300 historic buildings in two square miles makes it one of the historically richest, and most diverse architectural cities in New York State.
A Guide to Rhinebeck, NY
One of the earliest Upstate enclaves for New Yorkers, Rhinebeck has long been defined by its well-kept homes, deep-pocketed residents, and a village center that feels more like a movie set than a small town. With roots that go back centuries — and architecture to match — it’s a place where old money meets manicured charm, anchored by antique shops, legacy restaurants, and the slow rhythm of tradition. But in recent years, a quiet shift has begun. The arrival of Little Goat, an all-day café and bakery from Taavo Somer, has drawn a younger, design-conscious crowd to town. New shops like Upstate Down and Westerlind reflect a similar sensibility—polished, outdoorsy, and carefully curated. Soho House is also opening nearby, signaling a new wave of attention from the hospitality world. While Rhinebeck still holds tightly to its traditions, there’s a growing sense of reinvention — subtle, refined, and distinctly upmarket—folding into the village’s storied framework. ind all our Rhinebeck, NY recommendations below, including what to do in Rhinebeck, the best nearby hiking, plus eating, drinking and shopping favorites.
Spectacular Stays on The Water
There’s no better time to enjoy Upstate New York’s rivers, lakes, and swimming holes than right now. With long days, cool creeks, and high summer in full swing, we’ve rounded up some of our favorite getaways on the water — from design-forward cabins with private swimming holes to boutique hotels near rushing waterfalls. Whether it’s a quiet dip in the morning or an evening around the fire after a swim, each of these spots offers a perfect way to beat the heat — and make the most of summer’s sweetest weeks. Salvato Mill in Salt Point, NY Photos: Salvato Mill Two hours north of NYC in Salt Point, NY, the charming and ultra-unique Salvato Mill is an 18th century mill reimagined as an idyllic escape. Inside, the mansion is filled with a mix of antiques and mid-century modern furniture and decor. With a large living room centered around a fireplace that flows into a dining room with a 10-person table, the living areas are perfect for entertaining. Outside, there is a multi-level patio with a dining table and stainless steel glass grill, perfect for late summer evenings. The building features classic touches from its days as a functioning mill, including a waterfall that flows through the building and into the creek below. In addition to exploring the 11-acre property, relaxing on the patio, or gathering in the stone courtyard, guests can also enjoy the creek through the summer. This Design Forward Home Features The Most Surreal Outdoor Space Salvato Mill has an expansive history – its use as a gristmill and sawmill dates to the 1750’s. After stints as a cotton mill, cider mill, and even a button factory, the original mill burned down; its remains are still present, creating a surreal outdoor space where guests can dine and enjoy cocktails to the sound of rushing water Two Good Cabins in Roscoe, NY Photos: Clay Banks These Two Good Cabins, located on the peaceful, non-motorized Lake Muskoday, serve as the ideal getaway for those looking to live out their lakeside dreams. The cabins—one a spacious chalet, one a quaint guesthouse—are connected by a large wraparound deck, making it easy to move around the property. The deck also features an outdoor dining and grilling area that looks out onto the lake, with enough space for guests in both cabins to enjoy a shared meal outside. Guest perks include a pontoon boat, stand-up paddle boards, and kayaks, and the non-motorized lake is perfect for a relaxing swim (or float). For those looking to enjoy the lake views without getting in the water, the grounds have plenty of space for lawn games, relaxing around the fire, or lounging on the dock. Two Good Cabins: The Great Indoors The living room in the main ...
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Poet’s Hill in Hudson, NY
Located on a quiet country road outside of Hudson, NY, Poets Hill was designed with serenity in mind. Rent one or both homes on-site: its pool house accommodates up to four guests in two bedrooms, while its tiny house accommodates two. At the pool house, take advantage of the expansive outdoor area, with a large deck that's home to a Viking grill/BBQ, sink, and large dining table for al fresco meals, poolside. Its 82 foot pool is open May through October 1, weather permitting.
Goldie Point in Barnegat Light, NJ
100 miles from NYC, midcentury beach getaway Goldie Point is wonderful year-round, but would like you to know about "Secret September" and "Summer’s Not Over October." Currently it's September, the weather is still hot, the water is warm, and the masses of tourists are totally gone. A few months later, experience what the owners call “Wes Anderson Winter,” where the season and stillness create the perfect environment for recovery and wellness at the beach — in total solitude.
Mountain Terrace in Parksville, NY
Perched on a hill and surrounded by tall trees, Mountain Terrace is akin to staying in a luxury treehouse. Three bedrooms sleeps six guests at this beautiful Airbnb in Parksville, NY with two floors, two bathrooms and two living rooms. At the heart of the home is Mountain Terrace's porch: wrap-around style, with west-facing views to watch the sunset each day. A grill and large dining table are perfect for meals al fresco, under the surrounding swaying treetops. At night, head to the bonfire for stargazing outside the private yoga studio, also available for guest use.
Moody Pond House in Warren, CT
Less than 100 miles from NYC, find the magical Moody Pond House: a brand new, modern home tucked away on 18.5 acres in the impossibility picturesque Warren, Connecticut. Named after the gorgeous pond on the property, the popular rental home offers a cushy, private retreat year-round.
Catskills Cloud House in Phoenicia, NY
This gorgeous farmhouse has just been renovated into the perfect rental – especially for those wanting a quick, easy getaway without a car. Hop on the Trailways Bus and arrive into the small town of Phoenicia, where the house is just a 5 minute walk from Main Street. Walk into town for meals, or prepare breakfast, lunch and dinner in the beautiful kitchen and dining area. The trailhead for the Tanbark Trail is walkable from the house, as is the beautiful Esopus River for fishing, tubing, or just taking a cool-off dip.
Cherry Hill in Accord, NY
Midcentury vacation rental Cherry Hill in Accord NY sits atop a hill with panoramic views of the Shawangunk Mountain ridge. Drink in the views from its large hot tub — or opt to watch sunset from the living room, whose large stone fireplace is adjacent to a wall of windows overlooking the mountains. Stunning oversized windows throughout, multiple dining spaces and patios, a well-equipped kitchen and two cozy fireplaces makes this home the perfect destination for a retreat from the city any time of year.
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Modern Farmhouse Estate in Bovina Center, NY
Set at the end of a tree-lined allée with cascading waterfalls, this modern farmhouse is nestled into landscaped grounds overlooking the Bovina Valley and distant ridge lines. Defined by its seamless connection to nature, the home opens to wraparound porches, bluestone terraces, and French doors that frame sweeping views. Beyond the main residence, the property unfolds into gardens, outdoor rooms, and guest spaces — a Catskills retreat designed for both quiet living and convivial gathering.
The Beacon Firehouse: 1889 Landmark in the City’s Creative Core
Built in 1889, the Beacon Firehouse is a landmark of the city’s historic core, distinguished by its mansard roof, original bell tower, and arched windows. Once central to Beacon’s civic life, it retains much of its original craftsmanship – from ornamental plasterwork to finely crafted woodwork – alongside modern infrastructure. Today, its scale and adaptable layout position it for a new chapter, from cultural or community use to boutique hospitality, all within steps of Main Street’s shops, restaurants, and galleries in one of the Hudson Valley’s most active small cities.
The Wildflower Cottage in Woodstock, NY
Steeped in vintage character, the Wildflower Cottage is an early 1900s village home just a short walk from the center of Woodstock. The single-level layout is warm and easy, with original hardwood floors, crystal doorknobs, and paned windows that catch light throughout the day. Outside, a fenced yard and wraparound deck offer quiet moments among mature trees and flowering gardens. The grounds provide a serene setting where mature gardens and vintage character come together, reflecting the home’s thoughtful details and timeless appeal.
Charming Floral Studio for Sale in Saugerties, NY
Set in a sunlit storefront on Saugerties' main drag, The Dancing Tulip has spent the last decade growing into one of the region’s most trusted names in floral design. Offered as a full turn-key sale, this floral boutique blends artistic vision with a business built on thoughtful systems, steady revenue, and deep local ties. Ready to retire and pass the torch, the current owner offers the full operation – from organized books and vendor relationships to a small, skilled team — primed for someone eager to build on the shop’s reputation while infusing fresh energy and style. To support that momentum, the owner is open to staying on during the transition, offering introductions to established wholesalers, vendors, and clients to ensure a smooth handoff. Bring your own creative vision to this turnkey opportunity in the heart of Saugerties, NY. The business and rental space are offered together at $325,000. For inquiries, contact Hazel Sherburne, proprietor of The Dancing Tulip, at hsherburne63@gmail.com. Full details below.
Historic Farm Compound with Inn, Creamery & Storefront in Bovina Center, NY
Set in the heart of Bovina Center — a hamlet known for its agricultural history and quiet creative energy — this multi-structure compound spans more than 57 acres stretched over four parcels on both sides of Main Street. The offering includes a fully renovated five-bedroom inn, a two-bedroom carriage house, a historic storefront with commercial potential, and a restored dairy processing facility. The layout supports a range of uses, from hospitality and retail to food production or agri-tourism. Additional structures include original barns, dry storage buildings, and a new bridge over the Brush Brook that connects both sides of the property. With scale, infrastructure, and location, this is a flexible setup for a business-minded buyer or a team with a shared vision.
The Hudson Lookout in Catskill, NY
Perched on a high ridge above the Hudson River, The Hudson Lookout is a three-story tower that merges bold architectural form with a deep connection to its surroundings. Originally imagined as a sculptural “watchtower,” the three-story structure is oriented to frame long views in every direction – an approach that has earned features in Dwell, Wallpaper*, and Vogue for its bold vision and striking presence. With its minimal footprint and vertical form, the home offers a quiet but commanding presence in the landscape.