Holiday rentals in Kinderhook

Apartment w/Hudson-Electric Trail Access

This unique place has a style all its own with mid century touches. The apartment is newly renovated in the historical Abbott House in beautiful Columbia County with direct access to the Albany-Hudson Electrical Trail. 8 miles to Chatham, 25 min. to Hudson train station, and 1.5 miles to historical Kinderhook. 1 bedroom w/full bath. Private entry w/ patio directly off living area and a deck at the main entrance. Ample parking. Dogs welcome-must cleanup after them. No smoking/vaping, no parties.

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!

The Cottage on Sylvester Street

The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.

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.

Barn House: open layout isolated farm Hudson area

April lambing, October leaf peeping, summer swimming, winter by the stove: A century-old brick barn, eclectic style, much art, 10 miles from Hudson, near Kinderhook, secluded, unique residence. Gardens, sheep, and ponies are set off a country road, with a converted jungle shower, loft, and woodstove. Waterfall swimming area nearby. Empire bike path, e-bikes by request. Hudson Valley. The farm shares space with nature as it is - country life. Pony rides for children by prior arrangement.

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!

Hennett Hideaway: Spacious Home w Hot Tub & Pool

POOL OPEN THRU 10/14/26! Escape to this spacious 4BR, 3BA retreat on 3 private acres in the Hudson Valley. Just 5 minutes to Kinderhook and 20 minutes to Hudson, the home blends seclusion with convenience. Relax year-round in the hot tub, cool off in the seasonal pool, or gather around the firepit under the stars. With vaulted ceilings, a cozy fireplace, sunroom views, and plenty of space indoors and out, it’s the perfect getaway for family, friends, and Hudson Valley adventures.

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.

Modern and cozy 3 bedroom with outdoor oasis

Kick back and relax in this serene, stylish, and totally updated colonial home in Upstate New York. Enjoy views of a beautiful apple orchard and the Catskill Mountains, while relaxing in the back yard oasis, with a hot tub, dining area, gas fire pit, and gas grill. Located walking distance from local restaurants in the Village of Kinderhook and attractions, including the Samascott Orchard and Samascott's Garden Market. Drive 20 minutes to Hudson and 30 minutes to Albany.

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!

Pond Side R & R

Our home is a close drive from Hudson, Kinderhook or Chatham, NY and a ten minute walk to the Hudson River and a boat launch. Enjoy miles of country roads for walking and biking and our nine acres through meadows and woods on mowed paths. Guests have access to an Adirondack style cottage overlooking a pond. Close to numerous restaurants, galleries, antique shops and cultural activities. This property is good for couples, a group of friends and families.

Spacious 4BR Gorgeous Pool on 12 private acres

Escape to this sprawling, private, family-friendly 4BR 4-bath retreat close to historic Kinderhook & Chatham and 15 mins to bustling Hudson for endless dining & shopping. 30 mins to Ski Catamount! An outdoor oasis with salt water pool & large fire pit! Explore the picturesque bucolic grounds spanning over 12 acres complete with pond and old-barn. Step inside to discover all of the comforts of home with 3,200 sq ft of living space to entertain and relax!