Vacation rentals in Chatham Center

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

2BR fully-stocked home Chatham Villg Walk 2 MainSt

WELCOME ALL. Pedestrian/Bike friendly Village home 200' to Main St pubs/pizza/Crandall/Yianni's/Bimi's fine & fun dining. PS21/McHaydn live theatrs, shopping, town park w/swim pond/tennis courts w/in a mile. 12mi Hudson Amtrak (taxi, Uber avail). ArtOmi, Hawthorne Valley, Tanglewood near. Keyless entry. 100% smoke/pet-free property. Check-in 4pm/-out 11am. Free high-speed WiFi & parking at door. Fully stocked home. Private outdoor dining w/propane bbq. 2 guests max. Look forward to your stay 😊

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!

Sugar Shack | Romantic Tiny Home + Hot Tub

Sugar Shack | Romantic Tiny Home + Hot Tub. Celebrate Valentine’s all of FEB with complimentary roses-prosecco-robes-slippers! Escape to this 300 sq ft tiny home with private hot tub and she-shed. A peaceful, romantic getaway in the heart of Chatham—just steps from shops, dining, and theater. Only 2.5 hrs from NYC & Boston. Hike, explore, soak under the stars, or cozy up by the firepit. Thoughtfully designed for privacy, comfort, and indulgence. A blissful upstate NY retreat at @artparkhomes.

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.

Barn House: isolated sheep 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.

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)!

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!

Chic Hudson Farmhouse w/ Fireplace & Porch

1873 Stylish & cozy Hudson Farmhouse w/ a wood burning stove & the perfect porch. 14 minute drive to Warren St This 3 bedroom + office home has been lovingly updated while maintaining the original details of this historic property. Located on over an acre of land, on a quiet street, this peaceful retreat is the perfect escape to unwind and relax. With high ceilings, tons of oversized windows, and an open layout, this house feels both airy & bright.

Tiny House, Big Adventure; 20 min to Skiing

Welcome to "The Tiny" at The Hemptons in the Hudson Valley. The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Regretfully, we are unable to accommodate service animals due to the health risk it poses it the owners.

Harmony Valley Home, bright & inviting studio

You and your guests will be close to it all when you stay at our centrally-located home. The space is nestled perfectly between the Berkshire and Catskill Mountains, which provides countless opportunities for adventure! Whether a romantic getaway or a family vacation- you are an idea away from an unforgetable experience! Wineries & breweries Museums & art Hiking trails Empire State Rail Trail Conservation Areas Shopping

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.