Guesthouse vacation rentals in Ulster County

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Top-rated guesthouse rentals in Ulster County

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

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Top guest favorite

A charming 1950s cottage exterior features a rustic wooden facade with a welcoming front door highlighted by a window and shutters. Lush greenery surrounds the entrance, with flowerbeds and decorative stones adding character. A gravel path leads to the main door, creating a cozy appeal.

Guesthouse in Olive

4.99 out of 5 average rating, 136 reviews

The Lily Cottage Guesthouse

Tuck up in a thoughtfully renovated 1950s one bedroom cottage, perfect for a solo or a couples Catskill getaway! Situated in a quiet hamlet, nights in are lit by starlight and serenaded by peepers. Perfectly hemmed in by the Ashokan Reservoir, hiking, and the rail trail. The interior features a mix of vintage furnishings along with modern comforts. A 20 minute drive takes you to Rosendale, Kingston, or Woodstock for shops, breweries and excellent dining. Town of Olive Registration # STR-22-23

Guest favorite

A cozy seating area features a light-colored sofa and a red sofa, both positioned around a wooden coffee table. A modern area rug is laid beneath them, while strategically placed lights illuminate the space from above.

Guesthouse in Accord

4.93 out of 5 average rating, 162 reviews

Studio in Private Forest; Peace and Solitude

Set in a hemlock forest on a quiet country road, this newly redone and separate guest studio is a perfect getaway. Set on 30 private wooded acres, the property is bisected by a Class A trout stream. Guests have access to the shared pool Mon-Fri, but not Sat-Sun. The second floor studio has a queen size bed and a queen size sofa bed along with a private bathroom. There is Wifi, a television (ROKU). There is no kitchen, however, we do provide a microwave, dorm fridge and Keurig coffee machine.

Top guest favorite

A spacious master suite features a wooden accent wall and vaulted ceiling. A large bed with decorative pillows is positioned centrally, flanked by nightstands. In the background, a private bathroom is visible with modern fixtures and a wooden sink. Natural light filters through nearby windows.

Guesthouse in Woodstock

5 out of 5 average rating, 410 reviews

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "premiere" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1&1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE ondeck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

Guest favorite

A cozy living area features a leather sofa adorned with colorful throw pillows and a wooden coffee table. A black armchair complements the seating arrangement, while vibrant artwork hangs above the sofa. Natural light enters through two windows with light-filtering shades.

Guesthouse in Mount Tremper

4.97 out of 5 average rating, 353 reviews

Artful and Serene Woodstock Getaway

Please read description thoroughly before booking. Relax with a comfortable mix of rustic and elegant in this colorful studio with loft bedroom in the Catskill Mountains of NY. Midway between lovely towns, Woodstock and Phoenicia. Full kitchen and bath, cathedral ceiling, sleeps two adults comfortably. Due to allergies, we do not allow pets. This includes service animals. We use fragrance free laundry detergent. No smoking or vaping. This listing is not suitable for children or infants.

Guest favorite

A cozy living space features a stylish leather couch and a flat-screen TV. A wooden barn door leads to the adjoining bedroom, while natural light enters through two windows adorned with simple coverings. A plant adds a touch of greenery, enhancing the atmosphere.

Guesthouse in Kingston

4.95 out of 5 average rating, 224 reviews

Campfire Cottage: Fireplace, fire pit & no chores!

Escape the city and unwind at this beautifully designed home. Just 90 minutes from Manhattan, this is the perfect place to relax and reconnect with nature, or work remotely. Enjoy downtown attractions, hiking, and the Hudson River Maritime Museum nearby. The home features a cozy living area, full kitchen, electric fireplace, and no chore list for checkout. The yard has a grill and fire pit facing the woods. Book today to retreat to your private house and enjoy the beauty of Upstate New York!

Guest favorite

A bright sleeping area features a spacious bed against a backdrop of a sloped ceiling. A wooden bench sits at the foot of the bed, with a patterned rug laid beneath. Shelves display various decorative items, and natural light floods in from large windows.

Guesthouse in Accord

4.88 out of 5 average rating, 267 reviews

Sweet Cottage on a Farm Road

Simple, airy, studio cottage next to my house, featuring a woodstove & enormous bathroom with a clawfoot tub. Perfect for writers/solo-travelers seeking solitude & peace and couples wanting quality time together. The cottage is on a scenic country road, walking distance to 3 farms, including 2 great farm-to-table restaurants: Westwind Pizza/Apple Orchard, Arrowood Brewery, & Hollengold Farm. A stone's throw are Stonehill Barn and Inness. 15 min drive to the incomparable Minnewaska State Park.

Top guest favorite

A private cabin is nestled among lush greenery, showcasing a large deck with two Adirondack chairs positioned for relaxation. The cabin features large glass doors that open to the natural surroundings, enhancing the peaceful atmosphere.

Guesthouse in Kingston

4.99 out of 5 average rating, 144 reviews

Chic, Private Cabin with Stunning River Views

Private, fully renovated cabin with high-end finishes and stunning views of the Hudson River. All creature comforts including full kitchen, expansive living room, stylish bathroom and cozy bedroom, along with firepit and large deck to watch the eagles from. Nestled on a wooded corner of the owner's property but completely independent with separate driveway, parking and fenced yard for privacy. Just minutes from shopping/dining in Kingston, as well as world world class hiking and nature.

Guest favorite

The exterior of the cottage is shown, featuring a light-colored wooden facade and a steeply pitched roof. A spacious deck with wooden railings is visible at the front, surrounded by lush greenery and trees, enhancing the serene woodland setting.

Guesthouse in Kerhonkson

4.9 out of 5 average rating, 140 reviews

Cozy Catskills Cottage

Welcome to our cottage! We have 4.5 acres in the Catskills which includes a cozy cottage overlooking a babbling brook and next to a adorable duck pond. Come for peace, privacy, and relaxation that's only 2 hours from NYC. Cottage, 1 Bedroom, two floors, 800 sq. ft., full bath, fully furnished with a deck and patio furniture. Set back in the woods on a shared property off a beautiful farm road in Kerhonkson. 10 minutes away from the Shawangunk mountains and amazing options for hikes.

Top guest favorite

A vibrant purple door welcomes guests, adorned with a decorative wreath and accompanied by two potted plants. A black welcome mat is placed at the entrance. The surrounding walls are painted in a soothing aqua color, complemented by a nearby light fixture and decorative wall sign.

Guesthouse in Tillson

4.98 out of 5 average rating, 279 reviews

The Garden Studio: Private, Tranquil, & Central

Near New Paltz, Kingston, many other Hudson Valley destinations. Relax after a day of hiking, biking, climbing, & exploring the beautiful Hudson Valley in your private, clean & cozy cottage! This former artist studio's creative décor reflects local artists the area is known for. Your private patio features a fire table for comfort & ambiance. Complimentary snacks & S'mores provided. We're centrally located in the Hudson Valley - only a 90 min +/- drive from the NYC area.

Guest favorite

The exterior of a vintage cabin is framed by lush greenery and vibrant trees, including a striking red maple. The cabin features multiple windows, a small front porch, and is surrounded by expansive grassy areas, contributing to a peaceful, natural setting.

Guesthouse in Mount Tremper

4.93 out of 5 average rating, 113 reviews

Esopus Creek Hideaway

Summer spectacular on the Esopus! Clean remodeled 1 BDRM vintage cabin with modern amenities and sleek design interior. You will not want to leave this waterfront property with exquisite mountain views, both Hunter and Bellayre are just 15 miles away. All new kitchenette and bath easy no fuss mountain livin' situated on 2 private acres. Minutes to Phoenicia, Kingston and Woodstock. 3 Minutes to the infamous Phoenicia Diner! Cozy cute simple perfect getaway

Guest favorite

A shaded seating area is framed by lush greenery and wisteria, featuring a red swing and two chairs. Nearby, a charming red barn is visible against the clear sky, surrounded by well-maintained grass.

Guesthouse in Gardiner

4.96 out of 5 average rating, 251 reviews

Miller's Landing

We offer a beautifully renovated barn suite located under the picturesque Shawangunk Ridge. A place to relax with privacy. Located within biking distance of Mohonk and Minnewaska State Park. Proximity to historic New Paltz just 8 miles. We are nestled in the center of the Shawangunk wine trail and the Hudson Valley apple trail. Just a 10 minute car ride puts you at two amazing trail heads that offer mountain biking, hiking or an adventure in rock climbing.

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Guesthouse in Woodstock

4.84 out of 5 average rating, 575 reviews

The Carriage House: Studio

We offer a private studio apartment located on the second floor of this wonderfully restored 2 unit carriage house, built in the early roarin' 20's! It offers a blend of modern amenities, with more traditional countryside accents. The traditional design of the studio allows light to pour through the apartment, while making adjustments for sleeping in easy. This truly unique space is a perfect place to take a weekend to relax, and enjoy our exterior grounds!