Vacation rentals in Castleton-on-Hudson

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Top-rated vacation rentals in Castleton-on-Hudson

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

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Top guest favorite
A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.
Tiny home in Chatham
4.99 out of 5 average rating, 371 reviews

Boutique TINY home+private HOT TUB-walk to Main St

Sept. SPECIAL(Mon-Thurs): Includes Prosecco, s’mores kit, firepit supplies. Blush is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen & curated luxe design throughout. Tucked into a peaceful private oasis, yet only a 2-min walk to Main St. restaurants, brewery, shops & theater. Perfect for couples seeking a unique Hudson Valley getaway near hiking, galleries, great dining. @artparkhomes

Top guest favorite
A mid-century A-frame house is set within a lush landscape, surrounded by trees displaying autumn colors. A spacious driveway leads to the entrance, and a large deck with railings extends along the front, offering an inviting outdoor space.
Chalet in Averill Park
4.94 out of 5 average rating, 101 reviews

A Hidden Sparrow

/\ Keeping it cozy, yet modern. Our take on hygge minimalism. A Hidden Sparrow is a classic mid-century A-frame nestled on 60+ acres for hiking and has a picturesque creek that flows in the front of the property. With fresh upgrades, tasteful aesthetic and comfy accommodations, A Hidden Sparrow is an idyllic sanctuary offering complete privacy for your next getaway. This all season escape is the perfect place to disconnect from your typical dwelling and enjoy everything nature has to offer. /\

Guest favorite
A modern living space is featured with large windows allowing natural light to fill the room. Comfortable seating, including a plush sofa and stylish chairs, surrounds a wooden coffee table. A patterned area rug adds warmth to the sleek, tiled floor.
Home in Valatie
4.94 out of 5 average rating, 53 reviews

Majestic lake front house

Experience the ultimate retreat at our 2,100 sq ft 2 bedroom, 2.5 bathroom, modern lake front property. Enjoy swimming, fishing, free kayaking and paddle boarding on our Private Lake. Relax and unwind at our Outdoor Fire Pit or simply enjoy the picturesque view out of our floor to ceiling picture windows. Your Dream Family Reunion at our Secluded 26-acre Property awaits. We are also open to host a small, QUIET Wedding or similar event. There is no review yet, it is newly up for str.

Top guest favorite
An A-frame cabin is nestled within a forested area, featuring a striking black exterior and a sloping roof with wooden accents. Tall grasses and shrubs surround the entrance, creating a natural backdrop. A gravel path leads to the cabin, framed by lush greenery.
Cabin in Saugerties
4.97 out of 5 average rating, 167 reviews

Luxury A-Frame Cabin in the Woods with Sauna

🔨 Heads up: We’re currently making improvements to the property and there’s a chance of construction activity nearby on weekdays between 8am–4pm for the next few months. Evenings, nights, and weekends are completely peaceful and unaffected. 🏡 Modern A-frame in the Catskills with woodland views. Cedar barrel sauna, outdoor shower, smokeless fire table, and wrap-around deck. Queen bedroom with forest views, outdoor fireplace, fast Wi-Fi. Minutes to trailheads, waterfalls, and farmers markets.

Top guest favorite
The cabin features a charming exterior with a blue-gray wooden facade and a bright red door. Large windows provide natural light to the space. Two red Adirondack chairs are positioned on the stone patio, inviting guests to relax in the natural surroundings.
Cabin in Climax
4.95 out of 5 average rating, 83 reviews

Catskills Cabin on 100 Wooded Acres, Private Lake

Relax and refresh in this unique, newly renovated cabin on 100 wooded acres! Located minutes from the town of Coxsackie, the Hudson River and the Catskill Mountains, this historic cabin blends rustic charm and access to nature with comfort and convenience. High-speed WiFi and a fully stocked kitchen make this a perfect remote work destination. Ready to explore? Hike 3+ miles of on-site trails, swim or canoe in the lake, tour nearby breweries, orchards and antique stores or kayak the Hudson!

Guest favorite
Cabin in East Nassau
4.97 out of 5 average rating, 101 reviews

Luxury Cabin - Fall Foliage & 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 and chairs, Webber Grill, radiant floor, WFH space, and EV charging!

Top guest favorite
A spacious bedroom features a large queen bed with a white duvet and decorative pillows. Two sets of French doors open to an outdoor view, flanked by soft curtains. A cozy seating area with a light-colored sofa adds comfort, illuminated by natural light from the windows.
Guest suite in Valatie
4.98 out of 5 average rating, 289 reviews

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

Top guest favorite
A charming riverfront home is shown against a backdrop of the Hudson River. The two-story house features classic white siding with green accents. The surrounding lawn is well-maintained, and the expansive water reflects the sky's clouds and trees, showcasing the serene environment.
Home in New Baltimore
5 out of 5 average rating, 31 reviews

Whip's River House

Transport yourself to a magical 1850's riverfront home in the tiny hamlet of New Baltimore. With over 200 ft of private Hudson River frontage, it's a short walk through the back yard to dipping your toes in the water. Just over two hours drive from NYC, come enjoy a riverside bbq or evening fellowship around the fire pit under the stars. Take in spectacular views from the upper and lower porches while bald eagles and herons grace the sky. This is truly a one-of-a-kind experience.

Top guest favorite
A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.
Apartment in Coxsackie
4.99 out of 5 average rating, 163 reviews

Hudson River Beach House

Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

Top guest favorite
A spacious kitchen features modern appliances and elegant cabinetry. A gas stove is positioned beneath a stainless-steel hood, while a farmhouse sink is complemented by stylish fixtures. Light-colored countertops are paired with a herringbone backsplash, creating a fresh and inviting cooking space.
Home in Delmar
5 out of 5 average rating, 128 reviews

Rustic Farmhouse Meets Chic

This stylish and spacious home is perfect for family trips or small groups! Enjoy your privacy in this completely renovated three bedroom house, with full bathroom, and fully equipped kitchen. Located in the heart of Delmar, within walking distance to restaurants, bars, Stram Center for Integrative Medicine, and less than 10 minutes drive to Downtown Albany, Interstate 87 exit, 12 minutes drive to Albany Medical Center, and 20 minutes from the Albany International airport.

Guest favorite
A rustic cabin constructed with wooden planks and stone features is nestled among tall trees. Lush greenery surrounds the cabin, while a stack of logs is positioned in the foreground. A gravel pathway leads up to the entrance, enhancing the natural setting.
Cabin in West Sand Lake
4.96 out of 5 average rating, 352 reviews

The Lodge at June Farms

See more of us on Prime Video's tv show, June Farms... streaming now! This cabin is a stunning, rustic, open-floor-plan retreat. The screened-in front porch looks down onto our horse pasture. This cabin is our most romantic cabin on the property. Our gigantic rain shower in the bathroom has an 8'x5' wall mirror and a French door that opens out to the forest. If you are a cook, this cabin is a chef's dream. You might also like our stunning new cabin called The Farmhouse.

Top guest favorite
A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.
Cabin in Round Top
4.99 out of 5 average rating, 176 reviews

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Popular amenities for Castleton-on-Hudson vacation rentals