Holiday rentals with outdoor seating in Hudson Valley

Rustic Swedish Barn/Featured in Airbnb Magazine

Enjoy expansive views of the Catskill Mountains from this stunningly renovated Scandanavian barn. Featured in more than 10 magazines and catalogues, including AirBnB Magazine! Walk the property, with its big open fields, an organic orchard, walking paths, and flower gardens. A large private pond is swimmable (after heavy rains it does get muddy). The Barn has central heat and air conditioning. A full bathroom features an antique bathtub. Enjoy dining inside, or outdoor grilling and dining.

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. 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.

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.

Waterfront, Dog & Family Friendly, Cozy Cottage

El Girasol, "The Sunflower," a sunny, family and pet friendly cottage on the Esopus Creek in the Catskill Mountains. Our home is fully furnished with global & vintage finds. This charming cottage has 2 beds, spacious living room with a big, comfy sleeper sofa and cozy electric fireplace & fully equipped kitchen combined with a dining room. Creek access, BBQ, fire pit, fenced in backyard, & 2 decks makes our home a great destination for a relaxing getaway with family, friends and pets.

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Modern Prefabricated Architectural Retreat

At Stonewall Hill, a modern prefab home set on 10 wooded acres, you can enjoy a cozy night by the fire in winter & cook a feast in the well-equipped kitchen or on the outdoor gas grill in summer. It has an open plan kitchen, living & dining space; a main bedroom w/ queen bed & ensuite bathroom; a 2nd bedroom that doubles as TV room w/ queen sofa bed & bathroom across the hall. 10 minutes to the HITS fairgrounds & close to hiking, skiing, shopping, & dining.

Private Cottage/Mountain Views/Trails/Fire pit

A Unique Modern Cottage with Stunning Views / A Spa like Bathroom/ A Charming Gas Fireplace/ Fully equipped Chef's kitchen/Soapstone countertops/New premium appliances. Total Privacy High ceilings, hand plastered walls, antique doors. Glass French doors open to a private deck Enjoy big Catskill Mountain and seasonal Hudson River views. The large bath has a tiled glass door shower and a soaking tub. A Fieldstone fire pit overlooks the Catskills!

Willow Treehouse - secluded, unique, romantic

The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock. It is cozy, yet has all you need to cook dinner, enjoy reading, sit on the couch and stare outside the window, or swim. No WiFi and no cell service = fully disconnecting from daily life and true relaxation. Perfect for couples and solo adventurers (2 adults max). STR operating permit #21H-109