Tiny house vacation rentals in Columbia County

Charlotte’s Run Farm: Tiny Living, Big Views

Restored historic dairy barn (1910) on Charlotte’s Run, a retired Hudson Valley farm affectionately known as the (foster) Puppy Farm, whose use includes rehabilitating dogs via Mr. Bones & Co., a 501(c)3 nonprofit. This 400 sq ft studio cottage and deck offer Catskill Mountain sunsets and seclusion, one mile from Main Street, featuring Otto’s market, Universal Cafe, a wine shop, laundromat and more. Your farm stay helps us maintain the land so the dogs we foster here thrive! Permit GER-2025-014

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. 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.

Country Getaway Tiny House in Woods w/Pool/Sauna.

Tiny House - 600 Sq ft. of living space on 30 private acres with walkable trails in Columbia County. Secluded and surrounded by nature. House is fully equipped, sleeps 4 with queen bed and twin loft beds. Enjoy the pool, barn pool house and sauna. In the winter stay warm by the wood stove. Restaurants close by or stay in and enjoy the property. Located 8 miles from Hudson, 3 miles from Chatham and Kinderhook. Near OMI Arts Center. Adults only. Pool and sauna may be shared with other tiny houses

Romantic Getaway

Come stay at this sun-filled cabin in the Catskills ! This home away from home is all new construction and it contains all of the amenities you'll need to stay for just a weekend or for a whole week. The cabin is nestled in the woods, but it's centrally located near the town of Catskill, so you can have easy access to our popular ski mountains, our world renowned art scene and countless award winning nearby food destinations. Rich history of 17th century architecture, music and art await you.

Magical Private Island Retreat in Pine Plains

Enjoy the serenity of Twin Island Lake, surrounded by tranquil water, lush mountains and nature. this incredible private island retreat is only 2 hours from NYC. Take a canoe across a lily pad dotted lake to your own private island paradise. You will never find a magical space like this so close! The entire island is yours to enjoy and has plenty of outdoor spaces including a propane grill, hammocks and plenty of seating areas. The inside a humble aesthetic with wood paneling and charm.

1930's Cottage charm near hiking, air conditioned

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

Best mountain views anywhere

The bedroom window displays a picturesque view of the Berkshire hilltops. The fire pit offers a stunning view of the Catskill Mountains. This 27-acre property features nearly a mile of walking paths, is 3 minutes from Tivoli, 5 minutes to Bard College and Germantown, and 15 minutes to Hudson, Kingston and Rhinebeck. Across the street is the historic Clermont House, with picnic tables overlooking the Hudson River, and the famous Olana site is just down the road. Welcome.

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

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

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.

Peaceful Tiny House Escape by Hudson & Berkshires

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.