Holiday houses in North Chatham

Escape to Lakefront Leisure—Amazing views!

Welcome to this beautiful lake-front home on Kinderhook Lake, NY. Totally rebuilt in 2018, this home is designed to maximize the incredible view of the lake. Cool and sunny in the summer, and warm and cozy in the winter. Come and relax on Lake Kinderhook!! Brand new 6 person hot tub. Relax and unwind while 45 jets massage your muscles, summer or winter! Ever sit in the steaming hot water while snow falls around you? Upgraded 400/100 internet for work/school! About 2 hrs from New York City!

Kayaks and Colors-Lakefront Leaf Peepers' Retreat

Welcome to our paradise-where time slows down and memories are made. It's the perfect retreat for relaxing, kayaking, swimming, hiking, biking, and so much more. -Sip your coffee on the decks while enjoying lake wildlife -Grab a kayak or paddleboard and explore the 8 miles of shoreline -Catch the sunset, then end the day sharing stories around the starlit firepit An ideal base for exploring restaurants, breweries, wineries, galleries, historical sites, trails, farm stores, and orchards.

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.

Kinderhook Creek Private Retreat

Charming home at the end of a country road on the Kinderhook Creek surrounded by fields and woods with hiking/biking trails and a very private swimming hole! HVAC and a cozy fireplace make this a comfortable year-round getaway and a wonderful place to enjoy the fall colors! Within easy drive of endless things to do and places to explore such as the quaint town of Chatham (5 min), Tanglewood (35 min), antiquing in Hudson (20 min) and good skiing too (Catamount 30 min, Butternut 45 min)!

Farmhouse Retreat, Outdoor Dining/Fire-Pit & Golf

Escape to a thoughtfully restored 1800s farmhouse on 3 private acres beside Olde Kinderhook Golf Course—perfect for group getaways, family vacations, or retreats. + Sleeps 12 + King Beds + 3 Full Baths + Fast WiFi + Washer/Dryer + Stocked kitchen + Coffee maker + Four-season sunroom + Outdoor dining + firepit + Golf course views + Wooded privacy + Kinderhook Lake down the street + Smart TV + Board games + 10 min to Valatie & Kinderhook + 20 min to Hudson & Albany + 2.5 hrs to NYC

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.

Perfect Cottage On A Hill With A View

A peaceful cottage with views of the Hudson River and Sunsets over the Catskill Mountain Range. Personal, private and all inclusive this little cottage is an incredible place to unwind relax and soak in the beauty of the Hudson Valley. With easy access many local hikes, swimming holes, towns and shopping you’ll find This little cottage to be the perfect place to relax with nature & indulge in all of the luxuries that the Hudson Valley has to offer.

Holland House: Modern Rustic Guest Apartment

Thoughtfully designed two-bedroom apartment located above a former millinery shop built in 1880. Beautiful natural light. Mix of vintage and modern amenities, including two guest bedrooms, full kitchen and bath, high speed wifi, in-unit laundry and work desks. Private tree-shaded back porch overlooking Kinderhook Creek and Pachaquack Preserve. 20 minutes to Hudson. 30 minutes to Albany, the Berkshires and the Catskills.

Design Lover’s Blue Cabin

Blue Cabin is a cozy, design-forward retreat between the Capital Region and the Berkshires. Enjoy vaulted wood ceilings, a forest-green kitchen, and a spa-style bath. Outside, unwind in the covered lounge with U-shaped sectional, charcoal grill, and TV—or explore the backyard, where a creek runs through and a seasonal flower garden blooms. Peaceful, private, and perfectly located for both rest and adventure.