Vakantieverhuur in Old Chatham

Haddock + Cotter - Chic Farmhouse and Barn w/ Pool

This beautifully restored 1834 farmhouse blends historic charm with chic, modern comfort. Perfect for hosting family and friends, a holiday getaway, or a quiet country escape - designed for both relaxation and connection with cozy, elevated interiors. *Pool surrounded by lush gardens & a pergola *Barn converted into a luxe pool house *Basement gym (Peloton, punching bag,yoga&more) *Bar cart stocked for cocktail nights *Private, secluded setting immersed in nature Follow on IG @haddockandcotter

Architectural Marvel in Chatham with Pond and Art

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

Luxury A-Frame Cabin in the Woods with Sauna

🔨 Heads up: We’re currently making improvements to the property and there’s a chance of construction activity nearby on weekdays between 8am–4pm for the next few months. Evenings, nights, and weekends are completely peaceful and unaffected. 🏡 Modern A-frame in the Catskills with woodland views. Cedar barrel sauna, outdoor shower, smokeless fire table, and wrap-around deck. Queen bedroom with forest views, outdoor fireplace, fast Wi-Fi. Minutes to trailheads, waterfalls, and farmers markets.

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.

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!

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

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.

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

The Red House

Welcome to our historic and charming home, tucked away on 50 acres of beautiful, serene woodland. Built in 1840, our 2200 square foot residence combines the authenticity of centuries-old wood beams with cozy, comfortable interiors. The Red House is close to the charming towns of the Hudson Valley: Chatham, Kinderhook, Ghent and Hudson. There is also easy access to Tanglewood, Jacob's Pillow, Mass MOCA, Williamstown and Tannery Pond.

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.

Old Chatham Retreat | Skylight Over the King Bed

Hilltop Oasis is a modern-rustic, artist-designed retreat in Old Chatham with a king bed beneath a skylight, soaring ceilings, treetop views, and natural light throughout. Enjoy a chef’s kitchen, projector, wood stove, free Wi-Fi, laundry, and parking. Close to farm-to-table dining, wineries, sculpture parks, and Hudson Valley trails. Ideal for couples seeking comfort, culture, and countryside relaxation.