Places to stay near Hudson Chatham Winery

Book unique holiday rentals, homes and more on Airbnb

Top-rated holiday rentals near Hudson Chatham Winery

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1

Top Guest favourite

The charming farmhouse stands amid lush greenery, framed by mature trees. A wraparound porch invites relaxation, while well-maintained grass leads to the entrance. Large windows allow natural light to fill the interior, enhancing the welcoming atmosphere of the property.

Home in Ghent

Stylish Hawthorne Valley Farmhouse Retreat

Hawthorne is a renovated 1920s farmhouse set on 11 acres of pastoral fields, forest and pond, featuring stylish, comfortable, art-filled white and green rooms. Take in the view from the sun porch, nap on the big L-shaped sofa, share cocktails in the field overlooking the valley, and cozy up by the fieldstone fireplace at night. A fully equipped house, with Watson Kennedy goods throughout. Professional design, high quality kitchen equipment and accoutrement, linens, blankets and comforters, with Malin+Goetz & Molton Brown supplies make this your luxe country getaway. Now with unlimited WiFi. The perfect getaway for one to three couples, Hawthorne offers multiple rooms and lots of space for maximum relaxation and taking in the country. >> Enjoy the view from the sun-drenched front porch. >> Nap on the big L-shaped sofa in the living room. The two extra deep Restoration Hardware couches are 7’ long; they also serve as larger than usual single beds >> Cozy up with a book by the fieldstone fireplace in the fully screened back porch (with glass panels in Fall and Winter). >> Share sunset cocktails in the Adirondack chairs up in the field overlooking the valley. >> Cook in the well-equipped kitchen. >> Eat your candle-lit dinner in the dining room overlooking the valley. This is a fully equipped country farmhouse, with Watson Kennedy goods throughout the home. Professional design, high quality kitchen equipment and accoutrement, linens, blankets and comforters, and Malin+Goetz bath supplies make this your luxe country getaway. You will be the only guests in the house, with no one else on-site. Lots of hiking in the valley and nearby conservancy areas, biking on country roads, cross-country, downhill or snowshoe during the snowy months, or take in all the antique shops and history year-round. This peaceful property is minutes from the Hawthorne Valley Farm store, 20 minutes to the world-class food and vintage mecca of Hudson, and 30 minutes from the culture and history of Tanglewood, Jacobs PIllow and the Berkshires. For recreation there is hiking in the valley and nearby conservancy areas, biking on country roads, or cross-country, downhill or snowshoeing during the snowy months. Hawthorne is a 2-hour drive from NYC or a 2-hour Amtrak ride from Penn Station to Hudson, and then a 20 minute drive by car or taxi. The house is conveniently close to the Taconic Parkway, while set in a peaceful and quiet valley.

4.98 out of 5 average rating, 147 reviews

Top Guest favourite

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

4.99 out of 5 average rating, 159 reviews

Top Guest favourite

Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

4.97 out of 5 average rating, 109 reviews

Top Guest favourite

Tiny home in Chatham

Romantic-Private-Western Tiny Cabin w/HOT TUB

Sept. SPECIAL (Mon-Thurs): Prosecco/s’mores kit/firepit supplies. Just 2.5 hours from NYC, escape to The Hitching Post—a romantic Western-inspired tiny home in Chatham, NY w/private hot tub, firepit, outdoor shower & rustic luxury throughout. Once the hideout of a legendary samurai cowboy, this unique retreat features a cozy queen bed nook, luxe bath & kitchenette. Just a 2-minute walk to Chatham’s restaurants, shops, brewery & theater. A perfect Hudson Valley getaway for couples. @artparkhomes

5.0 out of 5 average rating, 105 reviews

Guest favourite

An open living space features a large sectional sofa surrounding a central glass coffee table. A decorative chandelier hangs from the exposed wooden beams. Natural light streams in through multiple floor-to-ceiling windows, revealing views of the surrounding greenery.

Barn in East Chatham

Luxury Barn Near Hudson with New Private Sauna

A secluded luxury barn retreat near Hudson and the Berkshires, now featuring a private sauna for year-round relaxation. Set on eight private acres where New York meets the Berkshires, this architect-designed 19th-century barn combines soaring ceilings, original beams and contemporary comforts. Enjoy a chef’s kitchen, two fireplaces, designer interiors, peaceful outdoor spaces and access to nearby Queechy Lake. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

4.96 out of 5 average rating, 114 reviews

Top Guest favourite

A bright and inviting living area features large windows that offer views of the surrounding greenery. A comfortable sofa and chairs surround a coffee table, while a desk with a chair is positioned near the window for a productive workspace.

Cabin in Ghent

Cozy chalet w/ deck, fireplace, by Hudson & hiking

Cozy 3-bedroom (5-beds), 2-bathroom home on 4 private acres in charming Ghent, NY. Recently renovated, Arch Bridge Chalet offers modern clean comfort with an open floor plan, luxury bathrooms, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. Surrounded by trees, trails, and streams, yet close to Hudson Valley farms, breweries, Berkshires skiing, and the vibrant town of Hudson. Perfect for hiking, biking, kayaking, skiing, and year-round getaways.

4.99 out of 5 average rating, 350 reviews

Top Guest favourite

The exterior of a two-story yellow house is set among trees under a clear blue sky. A full-width porch with simple wooden chairs and a table invites relaxation. Sunlight filters through the foliage, creating a tranquil atmosphere around the property.

Home in Ghent

Blacksmith House - Charming Historic Getaway

Built in 1790 as a blacksmith shop named “The Town Ax," Blacksmith House was rebuilt in the early 1990's and renovated by the present owners in 2017. The roughhewn beams of the original structure are exposed in every room. Approached by a grand stone staircase, set in a lilac-lined hamlet with plantings, surrounded by wildflowers, furnished with antiques and primitive Americana, Blacksmith House radiates tranquility and graciousness with its full-width front porch and classic proportions.

4.95 out of 5 average rating, 155 reviews

Top Guest favourite

The spacious kitchen features an island with a wood countertop and built-in storage. Mint green cabinetry offers a serene ambiance. Natural light flows through large windows, illuminating the dining area with a wooden table and cozy seating, creating an inviting space for gatherings.

Home in Ghent

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

At the end of a dead end road on 12 acres, you'll find the perfect retreat. Highlights include a natural swimming pool, yoga deck, outdoor Japanese hot tub and sauna. Chef's kitchen, grill and smoker. Living room has a piano and seats a large group. Outside there's a 3 level stone patio, deck and firepit w/outdoor sound system. Private yoga & in-home massage. Peloton bike, Temperpedic & saatva mattress, beautiful linens! *extra 6 guests w/rental of guest house!

4.98 out of 5 average rating, 135 reviews

Top Guest favourite

A spacious living area features a large, cushioned sectional sofa in a warm hue, complemented by a round coffee table. Natural light floods through tall windows, highlighting a minimalistic bookshelf and a stylish armchair in the corner, enhancing the room's cozy atmosphere.

Home in Hudson

Chic Hudson Farmhouse w/ Fireplace & Porch

1873 Stylish & cozy Hudson Farmhouse w/ a wood burning stove & the perfect porch. 14 minute drive to Warren St This 3 bedroom + office home has been lovingly updated while maintaining the original details of this historic property. Located on over an acre of land, on a quiet street, this peaceful retreat is the perfect escape to unwind and relax. With high ceilings, tons of oversized windows, and an open layout, this house feels both airy & bright.

4.98 out of 5 average rating, 125 reviews

Top Guest favourite

The exterior of the tiny house is presented, featuring a sleek, modern design with large windows allowing natural light. A spacious deck made of wooden planks leads to a seating area with a table and chairs, surrounded by open fields and trees.

Tiny home in Chatham

Peaceful Tiny House Escape by Hudson & Berkshires

Welcome to "The Tiny" at The Hemptons in the Hudson Valley. The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Regretfully, we are unable to accommodate service animals due to the health risk it poses it the owners.

4.99 out of 5 average rating, 289 reviews

Guest favourite

A charming country home is presented with a welcoming red front door. A pergola covers the entryway, surrounded by well-maintained landscaping that includes shrubs and a stone path. The exterior features light yellow siding, providing a warm, inviting appearance.

Home in Hudson

Bright, Airy Home in Hudson w/ TONS of Character!

Welcome to 514 Route 66! Conveniently located 5 min from historic Warren St, this bright and stylish country home is just minutes from downtown Hudson, where you can enjoy fine-dining restaurants, hip cocktail bars, art galleries, antique shopping, and more. Or, just relax, stay home, and sip coffee or wine in the sun-drenched living area, beneath the vaulted ceiling. A perfect mix of town and country, for a perfect upstate weekend.

4.83 out of 5 average rating, 308 reviews

Top Guest favourite

Townhouse in Hudson

Chic Hot Tub Escape | PetFriendly | Hudson, NY

Step into The Still — a moody, pet-friendly speakeasy-inspired retreat in Hudson, NY. Soak in your private hot tub in a fully fenced backyard, mix cocktails at the dedicated bar, and settle into decor guests say is even better in person. Hudson is the birthplace of the word "cocktail" — and this space celebrates that with style. Minutes from downtown, wineries, distilleries, and trails. Bring your pets — they'll love the yard.

4.94 out of 5 average rating, 116 reviews