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 favourite

Guesthouse in Kingston

4.94 out of 5 average rating, 135 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!

Dec. 6 – 13

$185 CAD per night

Guest favourite

Cottage in Rhinebeck

4.94 out of 5 average rating, 120 reviews

Refined, Intimate Cottage on Private Estate

Built in 1930, Bulls Head Cottage is a thoughtfully-designed retreat nestled within a 2.5 acre estate 5 minutes from Omega Institute and 10 minutes from the charming Village of Rhinebeck. The 720 square foot guest cottage is a relaxing place for up to 2 guests, offering cozy indoor and outdoor space including an office overlooking the property's pond. Enjoy quick access to hiking, shopping, fine dining and more. Under 2 hours from New York City by car or train. Pets not typically allowed.

Oct. 9 – 16

$397 CAD per night

Guest favourite

Bungalow in Saugerties

4.88 out of 5 average rating, 191 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.

Jun. 2 – 9

$171 CAD per night

Guest favourite

Cabin in Rhinebeck

4.91 out of 5 average rating, 296 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

Oct. 9 – 16

$256 CAD per night

Guest favourite

Tiny homes in Newburgh

4.88 out of 5 average rating, 527 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!

Dec. 17 – 24

$195 CAD per night

Guest favourite

Home in Pawling

5.0 out of 5 average rating, 186 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. **No parties **No smoking ~Ring Quests upon request at time of booking!

Oct. 12 – 19

$836 CAD per night

Guest favourite

Tiny homes in Hopewell Junction

4.96 out of 5 average rating, 463 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!

May 17 – 24

$446 CAD per night

Guest favourite

Guesthouse in Millbrook

4.86 out of 5 average rating, 223 reviews

Quaint Cottage near Millbrook Village

This space is a small cottage on our property located just a mile from the Village of Millbrook. The cottage is very private and removed from the main house. It features a queen-size bed, small bath with shower, and modest kitchenette with coffee/tea maker and refrigerator but no stove. The cottage is good for couples or solo adventurers. Small house-broken dogs are welcome. No cats, please.

Jul. 9 – 16

$218 CAD per night

Guest favourite

Tiny homes in Cold Spring

5.0 out of 5 average rating, 240 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.

Jun. 13 – 20

$198 CAD per night

Guest favourite

Cabin in Red Hook

4.96 out of 5 average rating, 305 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.

Sep. 21 – 28

$688 CAD per night

Guest favourite

Cottage in Poughkeepsie

4.91 out of 5 average rating, 301 reviews

Be in Nature at this Gorgeous Riverfront Cabin

Wappinger Cottage is a Scandinavian-inspired home featuring landscaped gardens leading to the shimmering Wappinger Creek. Inside, contemporary furnishings accented by bold patterns and pops of color create a sophisticated and inviting space. The house is designed to be cooled by cross ventilation. There are tower fans, but no AC. Pets allowed.

Jan. 9 – 16

$469 CAD per night

Guest favourite

Cottage in Ulster Park

4.94 out of 5 average rating, 186 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.

Mar. 21 – 28

$211 CAD per night