Barn holiday rentals in Dutchess County

1700s Farmhouse on 34 acres, Antique Lover's Dream

Antique charm meets modern comfort at Black Walnut Farm, an idyllic escape on 34 acres of woodland with private nature trails along a scenic creek. The stone house is a piece of living history built in 1747 by Dutch settlers, with lush gardens, 2 woodburning fireplaces, & eclectic antique decor nodding to a bygone era. Enjoy modern luxuries like state-of-the-art heating/cooling units, hi-speed WIFI, smart speakers, fully equipped kitchen, outdoor fire pit, & a hot tub to unwind under the stars.

Barn House Near Rhinebeck w/ Hot Tub!

This tastefully designed barn house is a very special Hudson Valley experience! The home has 2 loft like levels of living space and 4 separate sleeping areas. The 1st floor has an open kitchen, living room, 1 bedroom and full bath. On the 2nd floor there is a TV area, dining space and primary bedroom suite. The second floor also features 30 foot ceilings and original 1800s beams. On the 3rd level there is another bedroom, sleeping loft and full bath. Private yard with fire pit, stream and dock.

Cozy Mountainside Suite - Minutes from Beacon

The Equestrian Suite at Lambs Hill is a private estate with panoramic views overlooking the Hudson River & downtown Beacon. This beautifully-designed luxury suite sits atop a barn home to Icelandic horses & miniature donkeys, & features an outdoor hot tub, red light therapy, gourmet kitchen, & wrap-around decks. 1 mile to Beacon's Main St, 2 miles to Metro North train station & DIA: Beacon. We can host a max of 2 guests & have some dangerous features for kids so guests should be adults only.

Spilt Milk Cottage - Hudson Valley, NY

Completely renovated 1BR + den cottage inside a circa 1800's dairy barn. Come stay in a perfect WFH base with easy access to the Metro North train and everything the Hudson Valley has to offer. Master bedroom features a full size massaging and adjustable bed with plenty of storage and an office nook. The den is perfect for cuddling up and watching movies or the queen size foldout works as a 2nd bed. Highspeed internet, and a well equipped kitchen to cook up all those locally sourced goodies!

Red Barn at Turtle Rock Pond

Come stay in our very spacious converted Quaker barn built in 1803 and sitting on 7 idyllic acres! Enjoy the comfort of a 850+ sq ft living loft surrounded by nature on our little farm with only a 15 minute drive or less to the FDR Homestead and Presidential Library, Val-Kill (Eleanor’s Cottage); Vanderbilt Mansion; Culinary Institute of America, Vassar, and Marist. When in season, you can enjoy farm fresh eggs from our chickens and fruit from our orchard. We look forward to welcoming you!

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Named one of "The 10 Best Remote AirBnBs for an Escape From Reality" according to the author of 'Leave the World Behind' First Floor Open Space includes a fully equipped Kitchen (Viking Range, Dishwasher, Washer, Dryer, FridgeFreezer, Caesartone Counters), a Dining Room for 8 and a Living Room with Decorative Fireplace, Smart TV & Cable Second floor has 2 Bedrooms: One with a King bed overlooking the paddocks One with 2 Queen beds and a Desk overlooking the pool One bathroom with shower.

Country Suite Near Omega Institute & Rhinebeck

We designed our guesthouse with the comfort seeking guest in mind. Enjoy our comfy plush beds, soft bed linens, luxurious towels, and complimentary bath amenities for your ultimate getaway. Complimentary snack and beverage selections are also provided in our efficient kitchenette (no stove) which can accommodate light meals. Our 2nd floor guesthouse offers ductless HVAC to provide the ultimate comfort AC or heating as needed. Many guests comment on our relentless pursuit of cleanliness.

Sherwood Barn - close to ski mountain

Our guests stay on the SECOND floor of the barn in a 1200 Sq Ft, fully reno'd apt that sleeps 6. Located about 1 hour from NYC you will find peace and serenity in the middle of nature on this 4 acre estate (that also contains our main home) where you can get away from it all. unwind this way or visit local attractions like Thunder Ridge Ski Mountain, snowshoe/ X Country skiing, hike/bike/running trails, restaurants and local cafe's. Great oasis to kick back and spend time with family.

Rustic and Elegant Converted Barn

Two large Hotel -like suites plus a coffee/mini bar. This dramatic and handsome converted 19th century barn serves as my guesthouse. Guests enter at the front barn door and climb the stairs to your accommodations on the second floor- which has two air conditioned bedrooms, each with a bath en suite. The downstairs of the barn is not part of the accommodations but will also not be in use by anyone else while you’re enjoying a serene stay just outside the charming Village of Rhinebeck.

Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1

Step into the serene rural charm of the Hudson Valley for a unique retreat at our llama and alpaca farm. Nestled along charming country roads, our farm offers an escape from city life and the noise of modern living. Stay in a cozy apartment overlooking a peaceful pasture, where the absence of noise pollution lets you fully embrace the sounds of nature. Whether seeking to reconnect with the outdoors or savor the tranquility, our farm promises an unforgettable countryside experience.

(°) The Wandering Peacock (°)

The Wandering Peacock is a unique lodging experience. Outdoor spa, with a cedar hot tub and views of the Appalachian Trail, wood-burning sauna with herbs from the garden. The house showcases vintage machinery, a library, an outdoor kitchen with a pizza oven, and much more. Nestled within the forest foothills of the Appalachia trails, this converted barn is minutes away from downtown Kent and just walking distance from Bulls Bridge, the local river, and waterfalls.

Renovated mid/late 1800s Barn

Our peaceful 2-bed 1.5-bath newly renovated barn is a slice of paradise on a quiet country lane. It includes a colorful open kitchen and 24-foot ceilings. We are only 2 hours from NYC & a 7-minute drive to Rhinebeck village. Enjoy your morning coffee in a bucolic vegetable and flower garden, or take an afternoon swim in a heated saltwater pool (open May to October) with a large sunny bluestone patio with breathtaking views/natural splendor in every direction.