Cabin vacation rentals in Dutchess County

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Top-rated cabin rentals in Dutchess County

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Guest favorite

Cabin in Rhinebeck

4.99 out of 5 average rating, 472 reviews

Acorn Hill Cottage -A mid century farmhouse gem

No list of chores. Just relax! We are now accepting dogs on a case by case basis. Must inquire PRIOR TO BOOKING. Minutes to historic Rhinebeck Village, this quaint abode makes for the perfect romantic or mind clearing get away. Located directly off Route 9 tucked in the trees. Enjoy our completely separate art filled cottage. The open 550sq/ft studio floor plan will cheerfully accommodate couples & close friends. 4 persons MAX. Best suited for adult guests as the space is not child proofed.

Guest favorite

Cabin in Fishkill

4.96 out of 5 average rating, 91 reviews

Secluded Hilltop Cabin near Beacon & Cold Spring

3 private acres atop small mountain. Feels like your way upstate - check out the reviews! Hi-speed WiFi. Next to forest preserve and hiking trails. Furnished deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + pull out couch & twin-size mattress day bed on the porch. Perfect for 2, comfortable for 3, but 4 is probably max comfort since it's a small space. Please note that the road heading up there is steep. A car with AWD is ideal but a sedan will make it up too!

Guest favorite

Cabin in New Milford

4.94 out of 5 average rating, 177 reviews

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Guest favorite

Cabin in Holmes

5 out of 5 average rating, 27 reviews

A View From the Lakehouse

Welcome to paradise! Come meet your family’s new favorite vacation home, where your backyard is Dutchess County's largest private motorboat lake and your commute is less than 90 minutes from Manhattan. Lounge in the sun on our private dock, explore all the lake has to offer on our state of the art fiberglass paddleboards, and take in the stunning views from this beautifully renovated cabin, tucked away on a hillside amongst the lush foliage. Come enjoy lakeside living at its finest!

Guest favorite

Cabin in Wassaic

4.94 out of 5 average rating, 54 reviews

Cozy Hudson Valley House

Recently renovated A-Frame in beautiful Hudson Valley. Floor to ceiling windows bring in tons of natural light. The house sits up a hill with beautiful views of surrounding area. The village of Wassaic which has the super cool restaurant/bar The Lantern and the incredible community and arts space the Wassaic Project, is just a mile away . Sweet HV towns like Millbrook, Millerton, Kent and Lakeville 20 mins away. Skiing at Catamount 40 mins away. Tons of excellent hiking all around.

Guest favorite

Cabin in Pine Plains

4.98 out of 5 average rating, 199 reviews

The Upstate A - Modern Luxury in the Hudson Valley

The Upstate A is a 3 bedroom + sleeping loft, 2.5 bathroom A-frame set on a quiet cul-de-sac in the heart of the Hudson Valley. Built in 1968, it was fully renovated in 2020-2021. Staying here you’ll experience a cozy yet modern vibe, immersed in nature but with all the accoutrements of an upscale stay. You'll find great hiking in the summer, skiing in the winter, fresh upstate air year-round and serenity all day and night. See for yourself: check us out on IG @upstate_aframe

Guest favorite

Cabin in New Milford

4.95 out of 5 average rating, 138 reviews

Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

Our Little Creek Cabin is a place to pause. The cabin is located next to a rushing creek, where you can soak in a wood fired hot tub while listening to the sounds of the water. We are minutes from Candlewood Lake & Squantz Pond, where you take take our kayaks out. There are many wineries, breweries, towns to explore, antique shops, ski mountains, and beautiful hiking trails. Here you can simply open the windows to listen to natures sound machine! Find us on IG @thelittlecabins

Guest favorite

Cabin in Red Hook

4.99 out of 5 average rating, 138 reviews

Country Cottage Retreat. No Fee For Fido!

A great place to unwind, take strolls in the woods or along country roads. Watch deer and great-winged birds. . This two-bedroom, one bathroom cottage sits on 6 cleared acres with an additional 22 wooded acres for hiking. It has a cozy screened in porch and a beautiful stone patio, both with stunning views. There is ample outdoor space to enjoy the warmer months and is the perfect cozy spot when the weather turns colder. Less than 15 minutes drive to Rhinebeck and Omega.

Superhost

Cabin in Rhinebeck

4.88 out of 5 average rating, 342 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

Cabin in Dover Plains

4.86 out of 5 average rating, 7 reviews

A-Frame Getaway with Pool

Welcome to our stylish cabin in the beautiful Hudson Valley. Just a 1.5-hour drive from NYC. This recently renovated A-Frame offers 3 bedrooms and 2 bathrooms and a relaxing outdoor space with an above ground pool and a dining area for the perfect weekend getaway. Enjoy the convenience of local farms and farmers markets, vineyards and wineries as well as spectacular restaurants and scenic hikes such as the Dover Stone Church Cave and the Appalachian Trail.

Guest favorite

Cabin in Ancram

5 out of 5 average rating, 127 reviews

The Ancram A - Luxury Mid-Century Modern Cabin

Included in Curbed’s ‘Top 100 Airbnb’s around NYC’! Nestled between the Berkshires and the rolling farmlands of the Hudson Valley, The Ancram A is perfectly situated for your Upstate getaway. This unique A-Frame was originally built in the 60s and then reimagined in 2012 with modern luxuries. The cabin is on a lake so grab a towel and head down for a swim. We look forward to sharing our picturesque hamlet of Upstate NY with you.

Guest favorite

Cabin in Holmes

5 out of 5 average rating, 58 reviews

Cabin Charadora

Welcome to Your Dream Retreat! Discover the perfect getaway at our custom-built cabin nestled on a picturesque 5-acre lot in the Mid Hudson Valley. With 5 bedrooms, 3.5 baths, and a range of luxury amenities, this home blends comfort and elegance for an unforgettable stay. Whether you're relaxing in the hot tub, exploring nearby trails, or unwinding with friends around the fire pit, our cabin is your ideal home away from home.