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

4.94 out of 5 average rating, 172 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

Home in Pawling

5 out of 5 average rating, 212 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

4.85 out of 5 average rating, 104 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

Guest favorite

Cottage in Saugerties

5 out of 5 average rating, 357 reviews

Carriage House on Falls, Walk to Village

Welcome to 1903 Carriage House on the Falls — just down the hill from the vibrant village of Saugerties. This cottage blends modern comfort with rustic charm. Its cozy size makes it the ultimate escape for couples seeking a tranquil getaway. Admire panoramic creek vistas from the back deck. Enjoy the outdoors with a gas grill and waterside gazebo, unwind with board games, or relax with a movie on the SmartTV. As night falls, drift off to the soothing sound of the waterfall.

Superhost

Cabin in Rhinebeck

4.88 out of 5 average rating, 341 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, 608 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, 106 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 Hopewell Junction

4.95 out of 5 average rating, 498 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, 270 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, 337 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.

Guest favorite

Cottage in Ulster Park

4.95 out of 5 average rating, 214 reviews

Hidden Gem Cottage — cozy escape to play or WFH

Brand new open concept cottage with sleeping loft and kitchenette*......enjoy the privacy and quiet of your own indoor and outdoor space. surrounded by nature and adorable towns within 20 minutes. Come to relax and recharge . We want you to feel how we feel wrapped in comfort, quiet and nature *enough small appliances to cook in the space.