Guesthouse holiday rentals in Greene County

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Top-rated Guesthouses in Greene County

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Top Guest favourite

A warm bedroom is framed by sloped wooden ceilings and contains a spacious bed adorned with plush bedding. Two bedside lamps provide soft light, accentuating the wooden decor. A round window offers a view of the trees outside, enhancing the natural ambiance.

Guesthouse in Windham

Catskill Mts Artist Cabin Hike Dine Star Firegaze

Late Summer~Early Fall; Sweet Temperatures, Farm and Antique Mrkts., Hiking, Kayaking, Dining and Woodfires under the stars …Our storybook cabin is privately nestled in heart of the Catskill Mts, near seasonal stream and lake, under open sky surrounded by forest. Enjoy skiing, hiking, dining, antique and farm mkts. Experience true quiet, endless stars, staring into a wood fire, complimentary firewood, natural fabrics, authentic art/vintage design, full kitchen, rain shower, stone patio, grill.

LocationValueView

5.0 out of 5 average rating, 156 reviews

Guest favourite

The exterior of a charming multi-level lodge is presented, featuring wooden siding and a stone foundation. A staircase leads to a raised deck, with firewood stacked nearby. Surrounding greenery and distant mountains create a scenic backdrop, enhancing the lodge's rustic appeal.

Guesthouse in Hunter

Luxe loft with Hunter mtn. views on private estate

Loft apartment with amazing views on private estate. This manicured, unique property is in the center of Hunter village , but above everyone. Walking distance to restaurants, store and mountain. Southern exposure. Studio is located in independent private building with parking. Plenty play area for children. Heated floors, large tv, wood stove, full kitchen with dishwasher, propane grill 2 Queen Serta beds, +sleeper and large dining table. You will find everything for your Hunter Mountain getaway

LocationFamilyCleanliness

4.94 out of 5 average rating, 36 reviews

Top Guest favourite

Guesthouse in Cairo

Fall in Love with Slowing Down

A private romantic guesthouse with a vintage Scandinavian farmhouse touch, directly on the river. Enjoy morning coffee by the water or cook dinner in the wood-fired outdoor oven – firewood provided. The full kitchen is well stocked with olive oil, spices, and cookware. Great eats listed in our guidebook too. Your perfect base for swimming, fishing, bird watching, hiking, grilling by the beach fire pit, or simply relaxing with a movie in bed. Two hours from GW Bridge, 20 min from scenic Hudson.

LocationTVHiking

5.0 out of 5 average rating, 21 reviews

Superhost

A charming bungalow with a red exterior is nestled among tall trees. The angled roof features a small awning above a window with striped red and white curtains. A pathway leads to the front door, flanked by wild greenery and flowers.

Guesthouse in Catskill

StarryPines Cottage w Sauna Steps to Trails

StarryPines Cottage is a 1920s resort bungalow that has been brought back to life. The house features reclaimed wood pieces and local furniture finds alongside mid century modern touches that give it a unique and stylish appearance. The cottage sits on a scenic property at the gateway to the Catskills. Natural Beauty and amenities make this a perfect retreat. Our family including a sweet lab mix live on property across the drive and share the greater yard. Dogs are welcome on approval.

FamilyLocationSleep quality

4.87 out of 5 average rating, 244 reviews

Guest favourite

Guesthouse in Saugerties

Designer Catskills Cottage • Fire Pit + Creek

Stay in a beautifully renovated designer guest house set on 30 private creekfront acres in the Catskills, just 2 hours from NYC. Bright, airy, and thoughtfully designed, this upscale retreat offers access to gardens, old-growth forest, walking trails, and secluded swimming holes along the Kaaterskill Creek. Enjoy a private patio, fire pit, full kitchen, and peaceful natural surroundings near Saugerties, Woodstock, HITS, and Hudson. The property’s main farmhouse is also located on the grounds.

LocationValueOutdoor spaces

4.94 out of 5 average rating, 63 reviews

Top Guest favourite

Guesthouse in Athens

Athens Cottage

Welcome to your perfect Hudson Valley escape. This cozy two-bedroom cottage is nestled in the charming riverside village of Athens, NY, offering small-town charm, scenic beauty, and a relaxing home base for your stay. Inside, you’ll find a thoughtfully furnished space filled with natural light, comfortable bedrooms, and all the essentials for a stress-free getaway. Whether you’re sipping coffee in the morning or unwinding after a day of exploring, the cottage feels warm and inviting.

ValueFamilyHospitality

4.98 out of 5 average rating, 83 reviews

Guest favourite

The chalet stands amidst vibrant autumn foliage, showcasing a green exterior and a spacious deck. The well-maintained yard features a lush green lawn, with a variety of trees surrounding the property that enhance the natural setting.

Guesthouse in Windham

Alpine Chalet on Spectacular Property

Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

LocationValueBackyard

4.98 out of 5 average rating, 198 reviews

Top Guest favourite

A single-story cottage is set amidst lush greenery, featuring a welcoming porch and large windows. A stone pathway leads to the entrance, surrounded by well-maintained grass and shaded by surrounding trees.

Guesthouse in Cairo

Tomte Cottage in the Catskills!

Stay in the heart of the Catskills! 2 Bedroom Cottage with private entrance. One bedroom has a queen bed the other a twin/full bunk bed, suited for up to 5 guests! Cottage has full kitchen and bath w/shower. Wi-Fi and a 50 inch smart tv. Located 18 minutes to Windham and 30 to Hunter for skiing or snowboarding. Whether you are looking for a quiet weekend retreat or family weekend skiing trip, hiking or just exploring, this is the place for you! Self check in for your convenience.

ValueLocationBackyard

4.98 out of 5 average rating, 214 reviews

Guest favourite

A light-filled living area features a navy loveseat and a round dining table with two wooden chairs. The space is anchored by a patterned area rug on warm wood flooring. A door opens to a view of the greenery outside, inviting natural light indoors.

Guesthouse in Germantown

The Guest House

Welcome to The Guest House at Gatherwild Ranch, one of 8 accommodations on 15 acres of in the Hudson Valley. This cabin is a renovated 1800's guesthouse, just behind the main farmhouse. It is a comfortable space with a private lawn, kitchenette , firepit, electricity and wifi and is cozy yet spacious. It has 2 entrances, with beautiful morning and evening sun and features a queen size bed with fresh linens and shares the main bathhouse with beautiful Moroccan tiled showers.

LocationFamilyHot tub

4.97 out of 5 average rating, 73 reviews

Top Guest favourite

A serene view of the home's back deck is framed by lush greenery, showcasing large windows that allow natural light to fill the interior. The wooden deck features a railing, while the surrounding area has a mix of wildflowers and foliage, enhancing the connection to nature.

Guesthouse in Catskill

Walkable Village Guest House with Forest Views

Enjoy a stylish experience at this centrally-located home in the Village of Catskill, New York. You’ll be conveniently nestled on a village street while looking out on a wooded forest hillside behind this stand alone retreat, only a 7 min walk to the town of Catskill and an 11 min drive from Hudson and Hudson’s Amtrak station. Equipped with deep soaking tub, working fireplace, full kitchen, back deck, amazing natural light, and so many more details for the design inclined.

LocationFamilyWalkability

4.93 out of 5 average rating, 45 reviews

Guest favourite

Bright ceiling lights illuminate the open space, highlighting the wooden loft and ladder. Windows allow natural light to fill the room, with views of greenery visible outside. The walls are finished in a soft white, creating a light and airy atmosphere.

Guesthouse in Palenville

Studio Loft in America's First Art Colony

Open floor plan in an updated 100-year-old carriage house at the foot of the Great Northern Catskills and two hours from NYC. Our studio is close to hiking, boating, kayaking, fishing, hunting, horseback riding and walking distance to swimming holes. We're also near Woodstock, Saugerties and the HITS (Horse Shows in the Sun), Hunter and Windham Mountains, the famous Kaaterskill Falls and the Hudson River. A comfy, private space in tune with nature.

ValueLocationNearby

4.96 out of 5 average rating, 47 reviews

Guest favourite

Guesthouse in Saugerties

The Artist’s Studio | Guesthouse in Saugerties

Welcome to The Artist’s Studio, a cozy, light‑filled retreat tucked in the tranquil Catskills. This warm, inviting guest studio offers a peaceful escape after days spent exploring trails, browsing local shops, or visiting nearby towns like Saugerties, Woodstock, and Phoenicia. Whether you’re here to create, recharge, or simply enjoy mountain quiet, this serene space is a comfortable home base in every season.

LocationViewAccuracy

5.0 out of 5 average rating, 6 reviews