Holiday houses in Chatham Center

Sanctuary Banrn - Architectural Marvel in Chatham

Sanctuary Barn is a unique and spacious post and beam 2 bed, 2 bath home just outside of the Village of Chatham. Featuring two fireplaces, multiple levels, and stunning design, this is a one of a kind Hudson Valley home, appointed in thoughtful luxury. The grounds feature extensive stonework on the outdoor patios, a pond, and sculptures that you can discover as you wander the property. Nearby towns: Old Chatham (6mins), Chatham (17mins), Kinderhook (21mins), Pittsfield (29mins), Hudson (42mins

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.

Copper Top Mini Barn

Visit Columbia County NY for a refreshing getaway in our brand new, freshly renovated Mini Barn that sits on over 30 private acres. Enjoy the morning light, sunsets, moonlight, and star gazing over open fields. Walk the trails to beautiful views of the Catskills Mountains, listen to the singing birds or take a short drive to the best towns and villages in the Hudson Valley. You will leave The Copper Top Mini Barn feeling relaxed and recharged. Perfect for a fall getaway or a summer retreat.

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!

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.

Creekside Couple's Escape w/ Hot Tub Sauna & More!

Nestled beside a charming creek, our newly renovated cabin offers a peaceful escape where nature and comfort come together. Relax with your partner in the hot tub, on the covered deck, unwind in the wood-fired sauna, or sit by the fire in the gazebo. Enjoy the calming sounds of the creek and the outdoor views from every window. Discover nearby trails, quaint towns, lakes and waterfalls. Pet-friendly and ideal for couples looking for a unique getaway any time of year.

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.

Windswept! 3 Queen 2 BA NEW Outdoor Sauna & Shower

Welcome to Windswept Acres! -A 12 acre pastural mountain top setting with a Norwegian Inspired OUTDOOR 4 person SAUNA and SHOWER!. 3 BR 2 bath, fully equipped kitchen, dining room, 2 living rooms, a cozy pellet stove for added warmth on those chilly Fall/Winter evenings. WIFI for those working remotely. A great friend/family gathering place for those between NYC and Boston! Please see host and guest interaction access in information for guest section.

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.

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

Blush at Art Park Homes is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC & Boston. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen & curated luxe design throughout. Tucked into a peaceful private oasis, yet only a 2-min walk to Main St. restaurants, brewery, shops & theater. Perfect for couples seeking a unique Hudson Valley getaway near hiking, galleries & great dining. @artparkhomes

Private Luxury King Suite w/Breakfast

Escape to the Parker House Homestead, a private king suite in historic Kinderhook designed for comfort, quiet, 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.