Tiny house holiday rentals in Columbia County

Owls Nest Cabin c.1840 w/ fireplace & hot tub

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.

Vintage Shasta at Gatherwild Ranch

This lovingly restored 1963 Shasta Camper is a fun and unique experience. Complete with all original curved plywood detailing, enjoy a cute & kitschy throwback equipped with 2 full size beds, original kitchen with working propane stove, sink, electricity and fans. The design is breezy with lots of windows and air throughout. Outside enjoy a private table, firepit, and Adirondack chairs and all the amenities of Gatherwild Ranch including stand alone clawfoot tubs.

Top-Rated Tiny House on 70 acres

*25% Discount on Weekly Stays!* Welcome to "The Tiny" at The Hemptons in Upstate New York! 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.

Country Getaway Tiny House in woods w/Pool/Sauna

New Tiny House living space on 30 private acres with a mile of walkable trails in Beautiful Columbia County near Hudson/Chatham/Kinderhook. House has everything you need with a Queen bed, full bed, and full kitchen. The cozy space is an ideal getaway for relaxing. In the warm months enjoy the large in ground pool and renovated barn pool house. Enjoy the 6 person Sauna year round. ** Pool closed Mid-October - Mid-May, Confirm before booking.

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!

Boutique TINY home+private hot tub-walk to Main St

Romantic, boutique-luxe tiny home with private hot tub, firepit, and dreamy loft lounge. Plush queen bed, full kitchen, and curated charm throughout. A peaceful oasis just 2 mins from Chatham’s Main Street lined with restaurants, brewery, shops & theater. The perfect upstate NY getaway for couples—hike, visit galleries, stroll to dinner, or unwind in your own private spa oasis at @artparkhomes.