Tiny house holiday rentals in Columbia County

Owls Nest Cabin by creek c.1840 in Hudson Valley

The Owls Nest Cabin is ~ 2 hours from NYC yet just minutes to popular cities like Hudson/Catskill. An original Summer Kitchen circa 1840, it's been restored into a private 1 Bed/1Bath cabin with a claw foot tub, vintage kitchen, wood/brick walls, Vermont Castings gas fireplace, antiques & charm! Note: several historic barns share the land, situated on country road adjacent to historic registered farmhouse. Quintessential Hudson Valley. Hot tub, small natural swimming/dipping holes in creek

Farm Cottage, Views & Acres to Roam!

Restored historic dairy barn (1910) on Charlotte’s Run, a retired Hudson Valley farm affectionately known as the (foster) Puppy Farm for rehabilitating the dogs of nonprofit Mr. Bones & Co. This 400 sq ft studio cottage and deck offers Catskill Mountain sunsets and seclusion, while being just one mile from Main Street (Otto’s market and deli, Central House Tavern, a laundromat and renowned restaurant, Gaskins!) Your farm stay with us helps maintain the land so the dogs we foster thrive.

Rustic Barn Studio Apartment

Built from a saved, moved, & reconstructed 1850s- era barn from a former local dairy farm, this upstairs studio space features views of the Berkshire Mountains and walking paths on the 5 acre grounds. 20 mins from Jiminy Peak. 20 mins from Tanglewood Music Center. The space has a queen bed, sofa, kitchen area with fridge, sink, oven, stove, microwave, Keurig and coffee, toaster, and cooking essentials. **EV Charging Station coming sometime summer of 2023. We'll update when available.

Goose Landing Cottage by the lake with NEW Hot Tub

The cottage is a wonderful getaway for 2 people. Drive down a private road on the back side of a spring fed lake. See turtles eagles and geese. Swim or kayak from your own private dock. No motor boats allowed. The cottage is nestled back in the woods with your own private hot tub. A great place to get away, see wildlife such as deer, turkey, Canadian geese, an occasional fox. Best for a couple or a single person. Take a short stroll down a path to a wonderful spring lakefront.

CoZy Newly Renovated Cottage in Red Hook Village

'Solas Na Gréine' (Meaning 'light of the sun' in Irish) - Beautifully renovated private cottage located in the Village of Red Hook, New York. A perfect Hudson Valley getaway anytime of the year. Just 2 blocks (3 minute walk) to the town's center with wonderful cuisine, shops & small town charm. A short 5 minute drive to Bard College Campus, Hiking Trails, Orchards, Farms, & Wineries. Come relax, enjoy & explore upstate NY, just 90 miles from NYC.

Artist A-Frame at Gatherwild Ranch

Welcome to Gatherwild Ranch, an upscale, design-forward farm stay home to 8 beautiful and unique accommodations spread out on the rolling hills of a former apple orchard. Inspired by life upstate, Gatherwild offers guests everything from a pick-your-own veggie garden to artist-led workshops to luxury amenities – including a new to-this-year sunset deck, bathhouse, cold plunge tubs, and sauna – for a unique glamping experience in the Hudson Valley.

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.

Sugar Shack | Romantic Tiny Home + Hot Tub

Sugar Shack | Romantic Tiny Home + Hot Tub. 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.

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!