Holiday houses in Chatham

Beautiful space in the heart of Philmont

Enjoy the elegant ambience of this airy and bespoke space, just two doors up from the excellent restaurant Local 111, as well as the Co-op, where you can pick up delicious local produce, meats, and baked goods. A couple blocks from the Philmont Pub, another fantastic place to eat and enjoy the evenings. Minutes from Hudson, this town is literally in the center of Columbia County. A short drive to Catamount, Bash Bish, the Hudson River, the Catskills, the Berkshires, no end of places to explore!

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!

Cozy Retreat in the Trees

Time travel to 1958 in this architectural gem! This mid-century modern glass and wood cabin is 300 yards away from a charming small lake. The house is NOT on the lake itself, but it is surrounded by trees in a lovely secluded spot. The only heat is a wood stove... but there is a 4-person cedar barrel sauna in the woods that is electric. A classic 1952 Spartanette travel trailer serves as an extra bedroom. This is a true retreat for romance and adventure.

Tiny House, Big Adventure on 70 acres

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.

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.

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 Musuems Hiking trails Empire State Rail Trail Conservation Areas

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

This charming location is perfect for a weekend (or longer!) getaway. With enough sleeping arrangements for 5 people, the cabin is ideal for a couple or a small group of close friends/family. Linens and toiletries are provided, as well as a fully stocked coffee bar. Escape from the everyday & enjoy experiences like Art Omi, local wineries, downtown Hudson & Chatham, skiing, hiking and so much more!

Lovely 1 bedroom suite in historical house

Located just outside historic downtown Coxsackie, this newly renovated suite in a 220 year old Greek Revival house is within easy walking distance to tiny downtown Coxsackie and its restaurants and shops. 25 minutes to Hudson, 45 min-1 hour to the Catskill Mountains. I live above and next door with my dog George. It’s an old house, with all attendant creaks and charms.