Cabin holiday rentals in Dutchess County

Design-Forward Riverfront Cabin on 120 Acres

Far from the road, a tranquil modern cabin sits directly above a state-stocked fly-fishing and tubing river - an intimate, private escape under two hours from NYC. Set on a 120-acre property, with access to trails, river swimming, and a private cabin beach, you’ll feel completely secluded while still being 10–30 minutes from Red Hook, Rhinebeck, Hudson, and Kingston. Radiant floors, a Swedish composting toilet, Tesla Powered, w/ 500 Mbps fiber internet make it easy to unplug without sacrificing.

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Secluded Hilltop Cabin near Beacon & Cold Spring

3 private acres atop small mountain. Feels like you're 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!

Acorn Hill Cottage -A mid century farmhouse gem

No list of chores. Just relax! 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.

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.

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

Luxurious Private Log Cabin Retreat in Nature

Nestled in the serene woods of Hudson Valley, this celebrity owned log cabin offers rustic charm and modern comfort! Located on a large private property, the cabin features 3 bedrooms, 2 bathrooms and a beautiful stone fireplace. Enjoy some relaxation by the outdoor firepit or get active with one of the many things to do in the area. This comfortable log cabin is the perfect retreat for couples, families, small groups of friends, or solo travellers seeking an escape in nature!

Luxury Scandi Lakeside Cabin with Woodfired Sauna

Our Scandi cabin offers a serene retreat with stunning lakeside views that create a tranquil atmosphere. The wood-burning sauna invites ultimate relaxation, while the peaceful design focuses on simplicity and comfort. Surrounded by a breathtaking landscape, the cabin connects you with nature, making it the perfect escape to unwind, recharge, and enjoy the beauty of both the interior and the natural surroundings. A truly peaceful haven for those seeking calm and rejuvenation.

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

Secluded Mountaintop Getaway near Poughkeepsie

Featured in the Hudson Valley Style Magazine, this Modern Rustic Mountain Getaway is a unique option for accommodations when exploring the Hudson Valley/Taconic region. The secluded getaway is nestled on top of a steep hill and offers stunning views of the surrounding area. Kick back and relax in this calm, stylish space with an amazing outdoor deck or use it as a basecamp for exploring local hiking trails, wineries, distilleries, restaurants, and farms.

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.

Charming Lakefront Escape with Views

A year-round waterfront home with gorgeous unobstructed views of Whaley lake provides the perfect escape for a long weekend or vacation. Enjoy swimming and lake activities via private direct lake access. Spacious boathouse deck for entertaining or sunbathing. Cozy up to a two-story stone fireplace while enjoying the fall and winter colors. Just 10 minutes from Thunder Ridge Ski area.