Holiday houses 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.

Location · Value · Walkability

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!

Location · Family · Hospitality

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.

Value · Family · Indoor spaces

1860's Hudson River Carriage House Loft

Carriage house apartment on grounds of historic 1600's Dutch bouwerij (farm), yet with all of the modern amenities. Our Hudson river side apartment features original exposed beams, wood floors, tasteful decor, and a complete country kitchen. On-Hudson river edge setting with beach access allows watching eagles & herons, or kayaking. Walk-in to marshland wildlife refuge. 19th century lighthouse on property. Leaf peeping or apple picking during the fall. Hunter and Windham ski areas nearby.

Family · Location · Indoor spaces

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.

Family · Location · Hospitality

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!

Location · Family · Backyard

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

SEPT. SPECIAL: Prosecco, s’mores kit & firepit supplies. Blush is a romantic boutique tiny-home getaway in Chatham, NY—just 2.5 hours from NYC. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen and curated luxe design. Tucked into a peaceful & private oasis yet just a 2-minute walk from Main Street: restaurants, brewery, shops, theater. Designed for quiet couples’ getaways, with low voices appreciated outdoors in and around the hot tub. @artparkhomes

Family · Location · Getting around

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.

Location · Family · Getting around

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.

Family · Location · Getting around

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.

Location · Value · Hiking

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!

Family · Location · Bathroom

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.

Location · Value · Check-in