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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Guest favorite

Guesthouse in Maplecrest

5.0 out of 5 average rating, 120 reviews

Catskill Mt Artist Cabin Spring Hiking Star gazing

Storybook cabin, privately nestled in the heart of our beautiful Catskill Mtns, near babbling stream and lake, under big sky, embraced by tall pines, was designed by me, lifelong artist inspired by nature. Enjoy gazing into the stars, a fire, a swim, a hike, kayaking, dining in or outdoors relaxing at the cabin...with high speed wi-fi, indoor+outdoor wood stoves, natural textiles, antiques, art, full kitchen, stone patio, grill, firewood, washer/dryer and more. Lower midweek / longterm rates

May 5 – 12

R5,157 ZAR per night

Superhost

Guesthouse in South Cairo

4.94 out of 5 average rating, 108 reviews

The Catskill Artistic Retreat

This private cabin tiny house is set back from the main house I live in situated on over an acre of land. Just outside of the town of catskill, 15 minutes from hudson - this comfy cabin can be a creative retreat or romantic getaway- close to hikes, antiquing, restaurants! For those of you that have stayed here before I have completely renovated it to make it even more comfy - but still the same old vibe! New kitchen, appliances, bathroom with heated floors in bathroom, bathtub, cork floors.

Sep 20 – 27

R2,910 ZAR per night

Guest favorite

Guesthouse in Germantown

4.94 out of 5 average rating, 310 reviews

The Studio at Pear Farm

Sophisticated large studio has gorgeous light and Catskill Mountain Views Formally an artist studio, it has undergone an elegant renovation. The luxurious bathroom features premium tile and a glass walled shower The kitchen is new, nicely equipped and has a full sized refrigerator. Enjoy outdoor grilling and dining on the private deck. The studio is located on 65 pristine acres fronting directly on the Hudson River. 5 minutes to Germantown. 10 minutes to Tivoli, Hudson or Bard College.

Jun 10 – 17

R3,151 ZAR per night

Guest favorite

Guesthouse in Saugerties

4.99 out of 5 average rating, 244 reviews

Westhenge. An ambience with an eclectic mix

Welcome to Westhenge, our rustic inspired cabin nestled in the Catskill Mountains in upstate New York. 5 large skylights face north, creating a well lit studio. A kitchen supplied with a full set of implements to create your gourmet speciality, including a large crock pot. Old fashioned bath tub for soaking cares away. A deck with a panoramic mountains view, a beautiful Vermont Casting gas stove to keep you toasty and warm inside, and high speed Wifi, & Roku to stimulate your mind.

Feb 11 – 18

R2,940 ZAR per night

Guest favorite

Guesthouse in Elka Park

5.0 out of 5 average rating, 132 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, zip lining, 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.

Jan 2 – 9

R2,795 ZAR per night

Guest favorite

Guesthouse in Germantown

4.97 out of 5 average rating, 178 reviews

Loblolly Cottage

Loblolly Cottage is a peaceful retreat set among towering pines on our property in Germantown NY. This guest suite harkens back to an authentic 1930s Adirondack cabin that features a reclaimed barn wood interior with vaulted ceilings and antique beams. Outside enjoy our fantastic deck with a Cabana kitchen and fire pit. A short stroll will lead you to the heart of the hamlet where you will find an array of shops and restaurants. Loblolly Cottage is a unique one-of-a-kind vacation experience.

Jun 21 – 28

R4,437 ZAR per night

Guest favorite

Guesthouse in Saugerties

4.93 out of 5 average rating, 27 reviews

Catskill Views | Pet Friendly | Caraway 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.

Apr 24 – May 1

R2,052 ZAR per night

Guest favorite

Guesthouse in Windham

4.99 out of 5 average rating, 93 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.

Oct 14 – 21

R5,670 ZAR per night

Guest favorite

Guesthouse in Cairo

4.98 out of 5 average rating, 127 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.

Aug 30 – Sep 6

R2,819 ZAR per night

Guest favorite

Guesthouse in Catskill

4.92 out of 5 average rating, 127 reviews

StarryPinesCottage Steps to Trails w Sauna

Starry Pines Cottage is a newly renovated, 1950s resort cottage 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. We have outfitted the place to function for small groups with a fully equipped kitchen and flexible seating arrangements. We allow dogs on approval, so tell us about them and bring your furry friend. We cannot accommodate cats.

Nov 3 – 10

R2,675 ZAR per night

Superhost

Guesthouse in Elka Park

4.72 out of 5 average rating, 39 reviews

Little ski house

This roomy cottage has a 50-inch smart TV, king-sized, remote-controlled vibrating,adjustable bed, and a full sized futon. The kitchen has a stove,oven, microwave, and dishwasher. There is a ventless propane blue flame wall heater as well as abundant electric heat, as well as a decorative electric glass rock fireplace, there are 4 recliners built into the couch and love seat, and a dining area that seats four. there is now a Foosball table in the screenhouse.

May 27 – Jun 3

R2,525 ZAR per night

Guest favorite

Guesthouse in Germantown

4.96 out of 5 average rating, 188 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.

Oct 13 – 20

R2,318 ZAR per night