9 Charming Upstate New York Airbnbs for Design Lovers

Escape from the city and relax in one of these picturesque abodes.

Whether you’re too busy at work for an overseas vacation or you simply want a weekend away, taking an Airbnb staycation is the perfect middle-ground solution for cooped-up New Yorkers. Not only are upstate rentals just a two to three-hour drive from the city, but they also offer a much-needed respite from crowded subway cars and humid city streets. It’s no surprise that the upstate housing market exploded during the pandemic.

Plus, there’s a little something for everyone whether you’re looking for a historic manor with 15 acres of land or a quaint renovated barn brimming with antique furniture and kitschy art. Start planning your next weekend getaway with some of the best Airbnbs in upstate New York.

1. The Pond House Historic Artist Estate in Woodstock

You’ll want to leave city life behind for good after paying a visit to The Pond House in Woodstock. This idyllic estate was owned by acclaimed social realist painter Reginald Marsh and family, and has since been reimagined as a wedding venue, music video set, and a top- rated Airbnb. Inside, you’ll find an open-concept living-slash-dining space with floor-to-ceiling windows and an antique piano, plus a stunning master bedroom with panoramic views of the surrounding forest. Outside, you’ll find an expansive patio, private pond, and waterfall plus a fire pit and sun loungers.

2. The Airstream at June Farms in West Sand Lake

If you’re looking for a more rustic (but still Insta-worthy) experience, consider The Airstream at June Farms. This renovated caravan from 1984 features an airy, galley-style cook space with open shelving, a spacious wet room, Schoolhouse Electric lighting, and a king-size Casper bed topped with Ralph Lauren bedding. Outside, you’ll find a private salt water jacuzzi, fire pit, and a hammock surrounded by greenery for as far as the eye can see.

3. The Mountain Schoolhouse in The Catskills

There’s no better place to unwind from chaotic city life than this charming renovated schoolhouse. Located in the secluded Bovina Center, this one-bedroom is located off a quiet country road lined with beautiful wildflowers and mountain views. Inside, you’ll find reclaimed antique furniture and a clawfoot soaking tub, plus a cozy queen-sized bed fit for two. The views are so stunning, that you’ll forget it doesn’t have WiFi, TV, or cell service.

4. Windrift Hall Lakefront Sanctuary in Hudson Valley

Skip the six-hour flight to Europe and book this charming manor in Hudson Valley instead. Complete with wrought iron gates, a private spring-fed pond, ivy-covered walls, impeccable landscaping, and 14 acres of nature, Windrift Hall is straight out of an episode of Bridgerton. Inside, you’ll find five bedrooms, three bathrooms, a library, study, center hall, country kitchen, and a wood-burning fireplace in every room. Plus, you can speak with the host about coordinating a personal chef, yoga class, guided meditation, outdoor dinners, massages, and more.

5. This Old Hudson, Hudson Valley

The Old Hudson Maison is one of four units in The Old Hudson building that Anthony has renovated from top to bottom. Inspired by old-world luxury, this unit has a distinctly European feel to it. Step inside and you're immediately transported to the French countryside with each room dotted with vintage and antique pieces.

Tour the home here.

6. The Secluded Treehouse in Willow

Whether you’re looking to write the next great American novel or unplug with your significant other, the Willow Treehouse is calling your name. This custom-built oasis is nestled in the treetops just north of Woodstock and overlooks a small, swim-friendly pond. The wood-paneled space houses a cozy fireplace, floor-to-ceiling windows, a modern kitchen, and a lofted bed accessible via a ladder. In the backyard, you’ll find a patio, grill, and a pondside wood-burning Swedish hot tub.

7. The Scandinavian Barn in Germantown

This spacious renovated barn in Germantown is the perfect antidote to city living. With white walls, white floors, exposed wood beams, and hand-selected antiques, this space is Scandinavian minimalism at its finest. Kick back in the lofted queen bed overlooking the Catskill Mountains, unwind in the clawfoot tub, or take a dip in the private swim-friendly pond outside. Your rental also grants you access to 14 acres of open fields, hiking paths, and gardens.

8. The Artist Carriage House in Woodstock

Located on the same property as The Pond House, the Artist Carriage House allows you to experience the stunning Marsh family estate at a fraction of the price. This 800-square-foot abode features two bedrooms, an indoor fireplace, an open kitchen-dining space, a soaking tub, heated bathroom floors, and panoramic forest views. But you’ll want to spend most of your time outside, thanks to the outdoor dining space, charcoal grill, lounge chairs, and the private stream and swimming hole with a waterfall.

9. The Victorian Jungalow in Coxsackie

For a relaxing getaway that’s steps from the Hudson River and Main Street, consider the Victorian Jungalow. This antique home is equal parts classic and modern, with an authentic Art Deco-era kitchen and charming period details plus a TV projector, washer-dryer, and WiFi. In the backyard, you’ll find a tree-lined garden, fire pit, and a fenced-in yard that's perfect for pets.

Escape from the city and relax in one of these picturesque abodes.

9 Charming Upstate New York Airbnbs for Design Lovers

Escape from the city and relax in one of these picturesque abodes.

1. The Pond House Historic Artist Estate in Woodstock

2. The Airstream at June Farms in West Sand Lake

3. The Mountain Schoolhouse in The Catskills