Guesthouse vacation rentals in Greene County

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Top-rated guesthouse rentals in Greene County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

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

5.0 out of 5 average rating, 155 reviews

Catskill Mts Artist Cabin Hike Dine Star Firegaze

Summer~ Farm Markets, Hiking, Kayaking, Swimming, 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 very nearby skiing; Windham and Hunter Mts, hiking, dining, antique, farm mkts. Experience true quiet, endless stars, staring into a wood fire, w/complimentary firewood, natural fabrics, authentic art/vintage design, full kitchen, rain shower, stone patio, grill.

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Guest favorite

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

4.94 out of 5 average rating, 36 reviews

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

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Top guest favorite

Guesthouse in Cairo

5.0 out of 5 average rating, 16 reviews

Hard to Leave. Easy to Love.

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.

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Guest favorite

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

4.87 out of 5 average rating, 243 reviews

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.

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Guest favorite

Guesthouse in Saugerties

4.98 out of 5 average rating, 60 reviews

Designer Catskills Cottage • Creek Access + Hiking

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.

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Top guest favorite

Guesthouse in Athens

4.97 out of 5 average rating, 73 reviews

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.

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Guest favorite

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

4.98 out of 5 average rating, 198 reviews

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.

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Top guest favorite

A cozy living room features a light-colored sofa paired with two wooden chairs, creating a relaxed seating area. A rustic wooden coffee table sits on a textured area rug, while tall bookshelves display various decor items. Natural light filters through the windows, enhancing the space.

Guesthouse in Elka Park

5.0 out of 5 average rating, 157 reviews

Carriage House in the heart of Platte Clove.

You'll have a great time at this comfortable place to stay. Come be our neighbor. You will have the entire 2nd floor and backyard of our carriage house to yourself. We are located in the heart of Platte Clove with an abundance of hiking trails minutes from your door. Hunter mountain and Tannersville are only 10 minutes away with skiing, shopping and plenty of places to eat and drink. Our spot is the perfect location to explore the Catskills or kick back, relax, and enjoy the views.

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Guest favorite

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

4.97 out of 5 average rating, 73 reviews

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.

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Top guest favorite

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

4.93 out of 5 average rating, 40 reviews

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.

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Top guest favorite

A serene landscape features a heart-shaped pond reflecting trees adorned with autumn foliage. Rolling green hills lead to distant mountains under a clear blue sky, creating a calm and inviting natural setting.

Guesthouse in Hudson

5.0 out of 5 average rating, 64 reviews

Hudson Countryside Guest Cottage w/Amazing Views

Relax and unwind at this unique and tranquil getaway. This private guest cottage offers stunning views of the Catskill Mountains and heart-shaped pond. Explore the property and enjoy 15 acres of pasture and open land for you and your pet to roam. The perfect location for a relaxing getaway! Conveniently located central to Hudson, Catskill and Germantown (5 miles to each), where you can enjoy amazing restaurants, antique shops, art galleries and entertainment.

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Guest favorite

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

4.96 out of 5 average rating, 45 reviews

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.

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