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Tiny house holiday rentals in Columbia County

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Top-rated tiny home rentals in Columbia County

Guests agree: these tiny home rentals are highly rated for location, cleanliness and more.

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Top guest favourite
A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.
Tiny home in Chatham

Boutique TINY home+private HOT TUB-walk to Main St

Sept. SPECIAL(Mon-Thurs): Includes Prosecco, s’mores kit, firepit supplies. Blush is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC. 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

4.99 out of 5 average rating, 377 reviews
Top guest favourite
A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.
Cabin in Red Hook

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.

4.96 out of 5 average rating, 395 reviews
Guest favourite
A cozy living area features a dark sofa with decorative pillows, complemented by a yellow armchair. A wooden coffee table sits in the center, holding books, with a rug beneath. Natural light enters through two windows, illuminating the warm wooden walls.
Tiny home in Ghent

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

4.96 out of 5 average rating, 150 reviews
Top guest favourite
Aerial view captures a serene lake surrounded by autumn foliage. The vibrant colors of the trees reflect on the calm water, with a small island at the center. Lush greenery contrasts with the warm hues, providing a peaceful natural setting.
Island in Pine Plains

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.

4.97 out of 5 average rating, 110 reviews
Guest favourite
A gravel road winds through a dense, green forest, leading toward a wooden cabin nestled among tall trees. Direct sunlight filters through the leaves, casting dappled patterns on the ground. The serene surroundings create a sense of seclusion and tranquility.
Cabin in Catskill

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.

4.95 out of 5 average rating, 63 reviews
Top guest favourite
A pass-through window features a wooden countertop, displaying decorative items and a candle. A vibrant blue refrigerator and various kitchen appliances are visible in the background. The space is brightened by natural light, creating a cheerful ambiance.
Cottage in Catskill

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.

4.96 out of 5 average rating, 336 reviews
Top guest favourite
An open concept kitchen and living area showcases wood beam ceilings and shiplap walls. The kitchen features vintage cabinetry, a central island, and a gas stove in deep blue. Cozy seating options are arranged around a decorative rug, with natural light filtering through a window adorned with bamboo shades.
Cabin in Coxsackie

Cozy French country cottage by creek w/hot tub

Enjoy the best of the Hudson Valley we are minutes to the Hudson River and Coxsackie’s Historic Reed St. Centrally located to Hudson, Athens and Catskill for top dining/shops. Explore the Catskills to hike/bike/kayak. Complete chefs kitchen, Jotul gas fireplace, shiplap walls, original exposed wood beams, marble tiled bathroom showcase a cozy chic atmosphere that will quickly make you feel at home. Bonfire lovers and stargazers alert, you are sure to enjoy the evenings here in the hot tub!

4.98 out of 5 average rating, 100 reviews
Guest favourite
A spacious sleeping area features a queen bed with a textured green coverlet. A wooden accent wall and vaulted ceiling create a cozy ambiance. Natural light streams in through large glass doors that open to a private deck, complementing the warm wooden flooring.
Tiny home in Germantown

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 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

4.95 out of 5 average rating, 125 reviews
Guest favourite
A newly built tiny house is situated on a spacious lawn, surrounded by lush greenery. Large windows provide natural light, while a wooden deck extends from the entrance. The clear blue sky overhead complements the fresh, vibrant landscape.
Tiny home in Germantown

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.

4.94 out of 5 average rating, 47 reviews
Top guest favourite
An aerial view showcases a lakefront cottage with a warm-toned roof, surrounded by lush greenery. Two blue kayaks sit on the water, while a stone patio features a dining area. A fire pit adds to the outdoor space, blending with a wooden boat dock.
Cottage in Livingston

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

4.97 out of 5 average rating, 145 reviews
Guest favourite
An A-frame cabin with a wooden exterior is nestled amidst lush greenery. Relaxing Adirondack chairs surround a fire pit, while a picnic table offers dining space nearby. A hammock is stretched between two trees, with open fields visible in the background under a clear sky.
Tiny home in Germantown

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.

4.89 out of 5 average rating, 111 reviews
Top guest favourite
The exterior of the tiny house is presented, featuring a sleek, modern design with large windows allowing natural light. A spacious deck made of wooden planks leads to a seating area with a table and chairs, surrounded by open fields and trees.
Tiny home in Chatham

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.

4.99 out of 5 average rating, 283 reviews

Popular amenities for tiny home rentals in Columbia County

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly tiny home rentals

Guest favourite
Camper van/Motorhome in Germantown

Moonlight

4.88 out of 5 average rating, 179 reviews
Top guest favourite
An open living space features warm wood walls and concrete floors. A blue couch with yellow accents is positioned near a coffee table. Across the room, a dining area and kitchen are visible, along with natural light flooding in through large windows.
Farm stay in Chatham

Cozy, Charming Cabin Studio in Prime Hudson Valley

4.99 out of 5 average rating, 82 reviews
Guest favourite
A panoramic view of a serene spring-fed lake is depicted, bordered by lush greenery and trees. The calm water reflects the scattered puffy clouds above, creating a tranquil and picturesque environment. The natural setting offers a peaceful retreat with ample opportunities for outdoor activities.
Cottage in Valatie

Hudson: MV Buren Lake Cottage I

4.93 out of 5 average rating, 94 reviews
Superhost
A spacious saltwater pool is surrounded by a stone patio, featuring several reclining lounge chairs arranged beneath a large blue umbrella. A secure black fence encircles the area, while greenery can be seen along the pool's edge.
Flat in Hudson

Saltwater Pool 2 Bed Cottage@HudsonClearCreekFarm

5.0 out of 5 average rating, 5 reviews
Guest favourite
A light-filled living area features a navy loveseat and a round dining table with two wooden chairs. The space is anchored by a patterned area rug on warm wood flooring. A door opens to a view of the greenery outside, inviting natural light indoors.
Guest house in Germantown

The Guest House

4.97 out of 5 average rating, 73 reviews
Superhost
A charming seating area features two wicker chairs and a matching table adorned with a small succulent. Light filters through the glass-paneled door and a window, while colorful fabric drapes add a touch of warmth to the neutral walls.
Tiny home in Germantown

Pink Bungalow at Gatherwild Ranch

4.96 out of 5 average rating, 23 reviews

Tiny home rentals with a patio

Guest favourite
The exterior of a charming blue cottage is featured, showcasing a green metal roof and a vibrant yellow door. A small American flag is displayed near the entrance, and a low green picket fence borders the front yard with neatly trimmed shrubs.
Home in Catskill

The Railway Bridge Cottage

4.92 out of 5 average rating, 48 reviews
Top guest favourite
A private outdoor space features a wooden deck with a hot tub partially visible. A bright orange umbrella provides shade over a seating area with two chairs. The surrounding wooden walls and planters with flowering plants accentuate the serene atmosphere.
Tiny home in Chatham

Sugar Shack | Romantic Tiny Home + Hot Tub

4.99 out of 5 average rating, 514 reviews
Guest favourite
A scenic view of a lush green landscape features two contrasting structures nestled among tall trees. A modern black tiny house stands alongside a rustic barn, surrounded by native vegetation and a well-maintained grassy area, providing a peaceful retreat in nature.
Tiny home in Ghent

Country Getaway Tiny House in woods w/pool/Sauna

4.96 out of 5 average rating, 75 reviews
Top guest favourite
A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.
Tiny home in Chatham

Boutique TINY home+private HOT TUB-walk to Main St

4.99 out of 5 average rating, 377 reviews
Top guest favourite
An aerial view showcases a lakefront cottage with a warm-toned roof, surrounded by lush greenery. Two blue kayaks sit on the water, while a stone patio features a dining area. A fire pit adds to the outdoor space, blending with a wooden boat dock.
Cottage in Livingston

Waterlily Lakehouse - Modern+Waterfront+Retreat

4.97 out of 5 average rating, 145 reviews
Guest favourite
A newly built tiny house is situated on a spacious lawn, surrounded by lush greenery. Large windows provide natural light, while a wooden deck extends from the entrance. The clear blue sky overhead complements the fresh, vibrant landscape.
Tiny home in Germantown

Best mountain views anywhere

4.94 out of 5 average rating, 47 reviews

Tiny home rentals with outdoor seating

Top guest favourite
A modern farmhouse features a sloped black metal roof and a rustic wood exterior, surrounded by lush green trees. Two windows and a sliding door are visible on the side, alongside a covered porch that extends down a set of steps.
Home in Town of Ancram

Modern Scandinavian Farmhouse w/ Vintage Camper

5.0 out of 5 average rating, 70 reviews
Guest favourite
A serene view of a spring-fed lake is framed by trees, with gentle ripples reflecting the blue sky and clouds. Lush greenery surrounds the water's edge, contributing to a tranquil natural setting. The scene highlights the peacefulness of the 26 acres of private land.
Cottage in Valatie

Hudson Lake Resort: MV Buren Cottage III

4.91 out of 5 average rating, 76 reviews
Superhost
Two framed black and white feather prints are displayed on a rustic wooden wall. Above them, an animal skull is mounted, creating a contrast with the organic shapes of the feathers. The weathered wood adds a natural texture to the decor.
Cottage in Hudson

Saltwater Pool & Cottage Loft with Sauna in Hudson

4.85 out of 5 average rating, 40 reviews
Top guest favourite
An A-Frame cabin with a wooden exterior is surrounded by lush greenery. The entrance features a set of stairs leading to a deck, while a figure sits in a meditative pose on the vibrant grass, promoting a sense of tranquility in the natural setting.
Campsite in Town of Hillsdale

Sublime A-frame Cabin at Upper Shire Campsites

4.94 out of 5 average rating, 67 reviews
Superhost
The interior features a compact kitchen area with modern appliances, set against wooden cabinetry. A round table with chairs is positioned nearby, accompanied by decorative items. The staircase, leading to an upper level, is situated to one side, enhancing the space's cozy ambiance.
Cabin in Town of Ancram

Glamping A-Frame w/ Outdoor Shower on Hillside

4.8 out of 5 average rating, 10 reviews
Guest favourite
A light-filled living space features rustic white walls and wooden floors. A cozy soapstone stove stands beside a small seating area with a wicker chair and a couch. The doorway leads to a wooden-paneled area with hanging coats and boots, inviting a sense of home.
Guest house in Tivoli

Light-filled guest cottage

4.94 out of 5 average rating, 313 reviews
Guest favourite
The entrance of a charming cottage features a clean, white stucco facade accented by wooden shutters. A welcoming black door stands at the center, surrounded by lush greenery and colorful plants. A stone pathway leads to the entrance, enhancing the cozy outdoor atmosphere.
Home in Richmond

Berkshire Designer Cottage

5.0 out of 5 average rating, 7 reviews
Guest favourite
An antique brass bed is centered in the cozy guest room, covered by a white textured quilt. A bedside table with a lamp stands next to the bed. Warm yellow walls are complemented by exposed brick accents, and natural light filters through the window with sheer curtains.
Private room in Town of Hillsdale

Sweet Butter and Cream Guestroom

4.81 out of 5 average rating, 75 reviews

Destinations to explore