Vacation rentals in North Chatham

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 · View

Private Luxury King Suite w/Breakfast

Escape to the Parker House Homestead, a private king suite in historic Kinderhook designed for comfort, and relaxation. Enjoy premium bedding, a cozy sitting area, robes, towels/robe heater and a curated coffee-espresso station. Wake each morning to a fresh homemade breakfast, then unwind by the fire pit or explore the Hudson Valley from our convenient location near I-90, the Taconic Parkway, and the Albany-Hudson Electric Trail. Please note: Our property is adjacent to active railroad tracks.

Family · Location · Comfort

Cozy, charming cottage by the creek w/2 queen beds

Take it easy at this unique and tranquil getaway across from the Kinderhook Creek just outside of Malden Bridge, NY. Great for walkers, foragers, bike-riders, fishermen and fisherwomen, and lovers of natural beauty. Great fishing and swimming holes nearby. Well-supplied kitchen, washer and dryer, and lightning fast internet. Well-mannered dogs considered. Fenced in yard. I prefer no cats, as so many people are allergic (not me—I love cats), but exceptions can be made for a fee. Two queen beds.

Family · Location · Hospitality

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.

Family · Location · Access

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)!

Family · Location · Pets

The Hobbit House at June Farms

Watch June Farms on Amazon Prime Video! Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Highland cows, spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!

Family · Location · Cleanliness

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!

Value · Family · TV

Scenic Hilltop Home | Hot Tub, Fireplace, Home Gym

This hilltop house sits secluded above Kinderhook Lake, offering a peaceful escape with/ elegant interiors and lots of natural light. Cozy up by the fireplace, cook in the fully equipped kitchen, or unwind by the heated pool and hot tub. Enjoy this luxury retreat in the scenic Hudson Valley. *Enjoy 3.5 acres of privacy/breathtaking scenery *Heated pool & hot tub *Spacious basement w/ gym, pool table & cinema setup *Cozy living room w/ fireplace *Near Hudson & Jiminy Peak ski resort

Location · Family · Sleep quality

Monk's Bunk, Old Chatham

Forget your worries in this spacious and serene space. Tucked behind a large flowering hedge, Monk's Bunk is a rambling country home, surrounded by lawns, wildflowers and forest. Enjoy coffee on the back patio while listening to the brook and the birds. Stroll the forest path to Pinwheel Point overlook, or relax on the sunny front porch with a book. Haddock Hill Road is a cherished Dirt Road of Columbia County, and connects to the best hiking and biking in the Taconic Range

Family · Location · Accuracy

Huge Lakefront, Cozy Private Cottage in Upstate NY

GORGEOUS VIEWS, SWIM/BOAT/FISH/HIKE, WORK REMOTELY! ☀ 3 min to Electric Trail (hike or bike) ☀ 5 min to farm stands, BBQ, distillery ☀ 15 min to outdoor sculpture park ☀ 30 min to Albany, Hudson ☀ 40 min to Berkshires, Tanglewood, Great Barrington Sage Cottage sits on 120 ft of expansive frontage on Kinderhook Lake. Imagine tranquil mornings lounging on both decks, adventurous afternoons on the water and cozy nights in the gazebo or by the fire pit — it's all waiting for you.

Location · Family · Check-in

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.

Location · Value · Grill

Book for Fall! Private Lakefront | Kayak, Fish

100% 5-Star Reviews Casa Lago, a private lakefront retreat on Kinderhook Lake in the heart of the Hudson Valley. Step onto your private dock, launch a kayak, gather at the fire pit, or nap in the hammock. 2 hrs from NYC. 2 bedrooms + bonus studio, 2 full baths, 2 living spaces, and a lakefront kitchen — all facing the water. Pet-friendly + kid-friendly. Wineries, hiking, Tanglewood, + charming Hudson Valley towns! Experience the magic of Kinderhook Lake in every season!

Location · Value · Hospitality