Tiny house vacation rentals in Columbia County

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

1930's Cottage charm cozy air cond. near hiking

1 bedroom 1930's guest cottage with a living room. Near many hiking trails. Window air conditioner brand new, ceiling fans in living room and bedroom. Separate windowed bedroom with new full size mattress. Full size gas stove, microwave, fridge, Keurig coffee maker, toaster and large tiled counter and sink. Full bath off bedroom with large clawfoot tub and shower combination and sink and brand new toilet. Wifi , flat screen Smart TV. Vintage cast iron fireplace with electric insert.

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

Waterlily Lakehouse - Modern+Waterfront+Retreat

The Waterlily House is a Lakefront cottage at the North Twin Lakes in Livingston, NY, located just 2 hours from NYC. The lakefront cottage has been designed and decorated in a Frandinavian Style (Parisian chic and Scandinavian minimalism ). This chic 4 bedroom, 3 bath home, which can sleep up to 8 people, has been designed with an eye for detail, style, and relaxation. Follow us on IG @waterlilylakehouse for any last-minute cancellations/openings

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.

Country Getaway Tiny House in woods w/Pool/Sauna

Tiny house 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 barn pool house. Enjoy the 4 person sauna year round. ** Pool closed mid-October - mid-May. Confirm before booking. Adults only.

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!

Dome house - 2 Hours to NYC, Amtrak,Kaaterskill

A really really tiny house ,( smaller than most tiny houses) with a glass dome patio for stargazing. Two hours from NYC, close to skiing (hunter mountain/ Windham, Kaaterskill falls, Woodstock, Hudson, Saugerties. Enjoy facilities of a bigger house in a tiny form factor. Heat/AC, Queen bed, Hot shower, Kitchenette, cooktop, Fridge, Towels, linens, soap, coffee etc.

A sunny, quiet chalet beautifully decorated.

Welcome to our modern and sunny chalet nestled in the woods. Located directly across the street from Catamount Mountain Resort for year-round fun. Numerous hiking trails nearby, and Great Barrington’s dining and shopping minutes away. Relax in style and comfort and make unforgettable memories with friends and family. Please not that we do not allow pets.