Tiny house vacation rentals in Dutchess County

Find and book unique tiny house rentals on Airbnb

Top-rated tiny house rentals in Dutchess County

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

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Guest favorite

Guesthouse in Kingston

4.93 out of 5 average rating, 169 reviews

Campfire Cottage: Fireplace, fire pit & no chores!

Escape the city and unwind at this beautifully designed home. Just 90 minutes from Manhattan, this is the perfect place to relax and reconnect with nature, or work remotely. Enjoy downtown attractions, hiking, and the Hudson River Maritime Museum nearby. The home features a cozy living area, full kitchen, electric fireplace, and no chore list for checkout. The yard has a grill and fire pit facing the woods. Book today to retreat to your private house and enjoy the beauty of Upstate New York!

Guest favorite

Rental unit in Salt Point

4.9 out of 5 average rating, 123 reviews

Beautiful & Secluded Hudson Valley Rustic Getaway

Welcome to Ridgeback Farm at Salt Point! Newly renovated Hudson Valley rustic 1 bedroom apartment on former horse farm. The apartment is located above the barn, next door to the caretaker's apartment. Enjoy 22 acres of beautiful grounds, paddocks, heated pool, hot tub, and 3 ponds. Explore the property and all the Hudson Valley has to offer. Close to restaurants, cafes, Quattro's farm store, antique shops, Village of Millbrook, Innisfree Gardens, skiing. Hosts reside on the property.

Guest favorite

Home in Pawling

5 out of 5 average rating, 211 reviews

Hobbit House of Pawling

Cozy, one of a kind hobbit house with hot tub! **No children under 12 **No pets (Due to allergies) The ultimate private getaway. 2 bedrooms each with king size beds. 2 bathrooms each with walk in shower. Queen size pull out sofa bed in living room. 3 patios, bbq grill, 2 hammocks, 2 fire pits, electric fireplace in living room. -Hike the Appalachian Trail! -Visit all the historic Hudson Valley has to offer! **No parties **No smoking ~Ring Quests upon request at time of booking!

Guest favorite

Bungalow in Saugerties

4.88 out of 5 average rating, 232 reviews

Saugerties Cottage with Creek Access

Enjoy everything the Hudson Valley has to offer in this cozy home nestled between the Esopus Creek and the Village of Saugerties. Our cottage with original hardwood floors and vintage details has deeded access to the Esopus Creek for swimming and kayaking and is just a mile from the heart of the village. Relax with a book and glass of wine in the sunroom or spend the evening roasting marshmallows and watching the stars. A short drive from beautiful waterfalls, hiking trails, & skiing.

Superhost

Tiny home in Poughkeepsie

4.84 out of 5 average rating, 102 reviews

Lake Side Tiny House

Reconnect with nature at this unforgettable escape. Sitting on a beautiful 5 acre property, tucked back in the woods along a beautiful lake. Come stay and unwind. Plenty to explore and just be. Lake access for swimming or with paddle board, canoe, or kayak. Just ask and can be assisted with. The whole property has been curated to be a playground. Full bathroom inside unit. Brand new Mini Split heat and AC unit. Works amazing Has most kitchen amenities besides an oven. Enjoy

Superhost

Cabin in Rhinebeck

4.88 out of 5 average rating, 340 reviews

Sunset Bungalow-Mt views on 130acre forest & falls

Newly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, and comfortable bedroom- learn more at cascadafarm.com

Guest favorite

Tiny home in Newburgh

4.87 out of 5 average rating, 603 reviews

Cabin in the heart of the Hudson Valley, Cabin 2

Our little cabin is perfect for one or two guests for short stays while visiting local family, touring the areas wineries or nature trails, or for a clean, quiet over night stop while traveling long distances. Explore the Shawangunk Wine Trail, hike Minnewaska, sip cider at Angry Orchard, visit The Walkway Over the Hudson, or sample and shop the areas diverse farm stands and breweries. There is so much to see and do in the Hudson Valley and our cabin is close to it all!

Guest favorite

Cottage in Pawling

4.98 out of 5 average rating, 104 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Guest favorite

Tiny home in Saugerties

4.94 out of 5 average rating, 102 reviews

Tiny Cabin Outdoor Getaway Experience - Saugerties

The newest addition to our unique & eclectic collection of getaways! This cozy, unique and romantic tiny cabin provides you all the comforts that will help you unwind and reconnect. The outdoor kitchen helps you feel like one with nature. The outdoor shower under the stars will surely make your heart skip a beat. Stargazing by the fire pit will make you long for the nights to never end. Come back to nature...come back to yourself!

Guest favorite

Tiny home in Hopewell Junction

4.95 out of 5 average rating, 497 reviews

The GlassHouse: Hudson Valley Tiny Home w/Firepit

The GlassHouse is the much talked-about experience that we had crafted within a sprawling forest preserve. Its wrap-around windows allow breathtaking views to bring out the romantic in all of us! We are stone’s throw up against the Appalachian Trail right on the Dutchess/Putnam line and are less than an hour from Manhattan. Minutes from Fahnestock & Hudson Highlands State Parks & the Empire State Trail!

Guest favorite

Tiny home in Cold Spring

5 out of 5 average rating, 269 reviews

Tiny house on tiny farm close to hiking trails.

This space is a unique and private dwelling on 5.5 acres of property. The tiny house is a newly renovated modern and artistically designed space. Guests will have access to the back yard and wood lands. There are small trails and sitting areas that guests are free to enjoy. There is also a hiking trail walking distance down the street that leads to the Fishkill Ridge and Beacon.

Guest favorite

Cabin in Red Hook

4.96 out of 5 average rating, 335 reviews

Modern Upstate Cabin, near Rhinebeck NY

🏊🏽‍♂️Heated pool is open. (Will be winterized mid October Welcome to Maitopia. This beautifully designed passive glass and wood modern cabin offers elegant modern details and the warmth that only an upstate energy efficient retreat could. With a soaking egg tub, fires at every turn and a heated pool you will fall in love with the place and the towns nearby.