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

Guesthouse in Windham

5 out of 5 average rating, 136 reviews

Catskill Mt Artist Cabin Hiking Kayaking Dining

A storybook cabin, privately nestled in the heart of our beautiful Catskill Mtns, near a babbling stream and lake, under an open sky, surrounded by tall pines was designed me, by a lifelong artist inspired by nature Enjoy endless stars, fires, nearby skiing (Windham Mt Club, Hunter Mt Ski Bowl) swimming, kayaking (CD Lane Park) hiking, dining… OR just relaxing at the cabin...w/high speed wi-fi, indoor+outdoor wood stoves, natural fabrics, antiques, art, full kitch, stone patio, grill, firewood…

Guest favorite

Guesthouse in Catskill

4.9 out of 5 average rating, 196 reviews

StarryPines Cottage w Hot Tub Sauna Step 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.

Guest favorite

Guesthouse in Hunter

4.96 out of 5 average rating, 27 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 building with private parking. Plenty play area for children. Heated floors, large tv, wood stove, full kitchen with dishwasher, propane grill. 2 sofa beds, loveseat and large dining table - you will find everything for your Hunter Mountain getaway.

Superhost

Guesthouse in Saugerties

4.91 out of 5 average rating, 11 reviews

Carriage House Apartment

This is the entire top floor of a 1930's carriage house located on a former estate. The kitchen and bathroom were just renovated. The space has lots of windows with views of the Catskills to the west and the Berkshires to the east. The decor is a mix of modern, color, comfort and whimsy. The second "bedroom" has a queen bed and we are awaiting a custom sliding door (for now there are temporary curtains for privacy. This is a great place for a romantic getaway or up to 4 visiting the area.

Guest favorite

Guesthouse in Saugerties

4.91 out of 5 average rating, 57 reviews

Hits | Catskills Views | Pet Friendly | Studio

Book your Hudson Valley getaway and prepare for all-season adventures & relaxation overlooking the Catskill Mountains. The Caraway Studio is centrally located, an ideal home base to explore, work, relax, & recharge. Book this 1 bedroom / 1 bath that sleeps 3 and is fully equipped so you’ll feel at home. Across the street from HITS, only 1 mile to the hip and historic town of Saugerties, 15 min to Woodstock, 30 min to Hunter Mountain skiing, & all of the outdoors activities in the Catskills.

Top guest favorite

Guesthouse in Saugerties

4.97 out of 5 average rating, 39 reviews

Avalanche Farms private Guesthouse w/Stream Access

Stay in this clean and airy, truly upscale designer guest house! This sweet setup sits picturesquely on a 30 acre family farm a short drive from Saugerties. You will have access to swimming, hiking, fishing, skiing, shopping and all that the heart of the Hudson Valley has to offer. Farmers market on Saturdays, really good coffee and restaurants in town, and a patio with the calming sense of being on the land in all of its glory. Totally private and romantic with stream access 20 yards away!

Top guest favorite

Guesthouse in Windham

4.99 out of 5 average rating, 162 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.

Top guest favorite

Guesthouse in Cairo

4.98 out of 5 average rating, 177 reviews

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.

Superhost

Guesthouse in Coxsackie

4.78 out of 5 average rating, 65 reviews

Eagles Perch / Hudson River! Pet Friendly!

The guest house is located on the Hudson River in the charming village of Coxsackie. The space has a fabulous sunrise view, two bedrooms, and a beautiful tiled bathroom with a tub. There is a small refrigerator, microwave and coffee maker. The location is within walking distance to a wine shop, restaurants and a coffee shop. The yard is lovely and there is a dock to sit on next to the water to enjoy the late afternoon sun. In summer months, access to the pool. Unrivaled location.

Guest favorite

Guesthouse in Germantown

4.96 out of 5 average rating, 198 reviews

Luxe Guest House Retreat

Welcome to the Guest House nestled in the woods. We designed this lush and light-filled studio with peace and luxury in mind. Situated across from apple orchards, it sits ten minutes from Hudson and ten minutes from Germantown, you get the best of both worlds: country living with two amazing destinations close by. Ideal for a romantic getaway, or to be close to the sights and sounds but can retreat to natural beauty. A true sanctuary from the City.

Guest favorite

Guesthouse in Windham

5 out of 5 average rating, 8 reviews

Newly Built 1200sq ft Guest House 4 min 2 Ski/Hike

Beautiful newly built 1200 sq ft cozy log guest house, w vaulted ceilings and a gas fireplace for a charming indoor experience. Air conditioning for those few warm summer days. A mud room with bench seating and a ski storage area w a heated floor. An outdoor Adirondack chair seating area w a gas fire table for a peaceful outdoor experience surrounded by a serene tree lined environment.

Top guest favorite

Guesthouse in Germantown

4.99 out of 5 average rating, 219 reviews

The Loft

This beautiful loft apartment is located in the heart of Germantown- just 0.3 miles from Otto's Market (groceries and deli), And Universal Cafe. " farm to table global inspired classics." We offer tea & coffee in the loft, parking, yard access, wifi, basic amenities, full kitchen and a smart TV that has a fire stick with access to Amazon Prime and Netflix (no cable).