Guesthouse vacation rentals in Shandaken

4.99 out of 5 average rating, 153 reviews

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

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

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.

5 out of 5 average rating, 433 reviews

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

PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "PREMIER" 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

4.97 out of 5 average rating, 568 reviews

A charming guest house is nestled among lush trees, featuring a sloped roof and large windows. The exterior is painted in warm brown tones, blending with the natural surroundings. A gravel driveway leads to the entrance, providing access to a serene rural landscape.

Guesthouse in Bearsville

Relax on the Ridge - 2 miles from Woodstock

Stay and relax in a private guest house on a 5+ acre picturesque property overlooking historic Woodstock, N.Y. The cottage is nestled away high on a private road in a quiet country setting, yet conveniently only 2 miles from Woodstock and 10 miles from Phoenicia! Relax on the grounds while watching our Tennessee Mountain, Cashmere & Kiko goats—drive into town to enjoy shops, restaurants, & the unique artistic culture of Woodstock—explore the many beautiful trails that the Catskill Park offers.

A cozy living area features a stone fireplace with a wood fire burning inside. A colorful couch adorned with various patterns is complemented by a stylish chair. Natural light enters through large windows, and a rustic table is visible in the background.

4.97 out of 5 average rating, 381 reviews

Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace

Snuggle by a roaring fire. Eat in a corner nook or at a rustic wooden counter by a window. This quaint, whimsical home has a private deck w/bbq, a garden with a hammock and fire pit. A full size Murphy bed with a full kitchen (except for an oven). You will have access to the entire guest house. A short drive to the beautiful, eclectic, funky town of Woodstock. Art & culture, restaurants, hiking & biking all nearby. Electric heat, ceiling fan, a standing ac unit and single person shower.

A cozy sleeping area features warm wooden paneling and a spacious bed topped with a striped blanket. A colorful, patterned cushion adds a pop of color. Framed artwork is displayed on the walls, with a warm glow from wall sconces illuminating the space.

4.87 out of 5 average rating, 1,000 reviews

Rocket Room - Rock Stars Only

Walk to town, hiking or a swimming hole. A popular vintage look cabin that backs up to a private woods but is steps from all Woodstock has to offer. Long time superhosts. Turn on, Tune in, Drop out in our 70's rock & roll hideaway carved out of a converted 1920s carriage house. This ain't your Grandma's cabin. All our units have been featured in videos, films, and photoshoots. This one has been featured in Playboy and Imperial Publishing arthouse book. Town of Woodstock OP #27.54-1-12

Guesthouse in Mount Tremper

The exterior of a green cottage is presented, featuring a sloped roof with burgundy trim. Two comfortable chairs sit on the porch, alongside a small table. Lush greenery surrounds the property, enhancing the inviting setting.

4.97 out of 5 average rating, 371 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, closet, cathedral ceiling, sleeps two adults comfortably. Due to allergies, we do not allow pets. This includes service animals. Not suitable for children or infants. No smoking or vaping. We use fragrance free laundry detergent.

4.99 out of 5 average rating, 162 reviews

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

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.

4.99 out of 5 average rating, 187 reviews

A cozy living space features a gray sectional sofa adorned with textured pillows and a soft throw. A rustic wooden coffee table sits within reach, complemented by a gas fireplace framed in warm wood. Natural light floods the area through a skylight, enhancing the inviting ambiance.

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.

4.98 out of 5 average rating, 199 reviews

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.

Guesthouse in Olivebridge

A serene bedroom features a spacious bed adorned with decorative pillows and a soft throw. Nightstands with lamps are situated on either side. Natural light filters through two windows, complemented by light-colored curtains, creating a calm and inviting atmosphere.

4.95 out of 5 average rating, 189 reviews

The Ashokan Guest House

This newly renovated guest house is attached to a 120 year-old farmhouse which originally housed the workers building the Ashokan Reservoir. This quiet refuge sits on a lovely 3-acre lot in Catskill Park within .5 mile of Ashokan Reservoir. An outdoor adventure in our beautiful Catskill Mountains awaits any direction you go. This is the perfect location for couples or individuals looking for a retreat (it is not child-proofed). Near Kingston, Woodstock and Stone Ridge.

Guesthouse in Margaretville

The exterior of a Craftsman-style studio is shown, featuring a two-car garage with wooden doors. The building is accented with earthy tones of red and gray, while ambient lights illuminate the front in the evening glow. Surrounding trees enhance the natural setting.

4.98 out of 5 average rating, 184 reviews

Sunny Arts & Crafts Loft

Spring skiing & boarding nearby at Belleayre & Plattekill. Late winter hiking. Year-round relaxing! The Loft is a great base for your visit. Explore fun towns like Margaretville & Andes. The Loft is a cozy, private spot to unwind in a peaceful mountainside location. Super savings on longer stays! Our private road is plowed and sanded. To ensure smooth WINTER travels, please make sure to bring an AWD vehicle with winter tires. No AWD needed rest of year.

Guesthouse in Mount Tremper

A cozy cottage is featured under a layer of fresh snow, with a dark exterior complemented by a vibrant red door. Two windows on the left provide natural light, while a pair of chairs sit invitingly on the porch, surrounded by a serene winter landscape.

4.92 out of 5 average rating, 374 reviews

Cozy Catskill Cottage Perfect Getaway for Two

NEWLY RENOVATED, COZY, CLEAN, PRIVATE AND SECURE Cottage in scenic and peaceful locale. Convenient and easy to find near the town of Phonecia, NY. 100 PACES to the ESOPUS RIVER and its trout fishing, trail heads and scenic hikes less than a mile away. Close to numerous sophisticated dining and shopping options. Less than 30 minutes to BelleAyre and Hunter Summer Happenings. Perfect for couples who need a weekend country getaway.

Popular amenities for Shandaken guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

4.91 out of 5 average rating, 44 reviews

A welcoming entrance to Claudia's Cottage features a dark-front door with a grid window. Red metal chairs and a matching table are positioned on the wooden porch, surrounded by a natural setting with scattered leaves on the deck.

Guesthouse in Saugerties

Claudia's Cottage

4.92 out of 5 average rating, 75 reviews

A guest house is depicted with warm brown siding and green accents. A wooden ramp leads to the front door, providing accessibility. Several large windows allow natural light, and the surrounding trees create a tranquil, wooded setting.

Guesthouse in Hurley

Charming 1 Bedroom Guest Cottage

5 out of 5 average rating, 13 reviews

Guesthouse in Hudson

Modern Farmstay Cabin in the Woods

4.99 out of 5 average rating, 102 reviews

A spacious interior featuring hardwood flooring and a vaulted ceiling. A comfortable seating area includes a white sofa and a circular coffee table. A large bed is set against the wall, and the kitchen area is visible in the background, showcasing modern appliances.

Guesthouse in Hurley

Hillside Hideaway with Hot Tub

4.92 out of 5 average rating, 103 reviews

The outdoor space is illuminated by soft lighting, enhancing a peaceful atmosphere. A fountain adds a gentle sound, with water flowing into a stone-lined area. The carriage house can be seen at a distance, flanked by trees and set amidst an open lawn.

Guesthouse in Oneonta

Calhoun Carriage House

Guesthouse in Stanfordville

A bright living room features a sofa facing large glass doors that open to a view of the forest. A cozy armchair is situated nearby, along with a simple coffee table. A bookshelf contains various items, and a wood stove is positioned in the corner.

4.93 out of 5 average rating, 190 reviews

Eco Cottage in the Woods

Superhost

An airy living room is showcased, featuring a comfortable seating area with a sofa and armchair. A glass coffee table holds books, while large windows allow natural light to fill the space. The room is oriented towards a dining area, visible in the background.

Guesthouse in Mountain Dale

4.94 out of 5 average rating, 64 reviews

Willow House Cottage

4.92 out of 5 average rating, 61 reviews

Beautifully Renovated Woodstock Cabin with Sauna

Guest house rentals with a patio

Guesthouse in West Shokan

A modern living space features a wooden dining table surrounded by white chairs, illuminated by ceiling lights. A cozy sofa is positioned nearby, with a hidden TV set within a wooden wall. Large windows offer views of the surrounding greenery.

5 out of 5 average rating, 31 reviews

Modern Nature Escape w/Barrel Sauna & Yurt

5 out of 5 average rating, 11 reviews

Guesthouse in Hurley

Cozy Cottage with View Mountain-Ashokan Reservoir

5 out of 5 average rating, 16 reviews

Guesthouse in New Paltz

The Pool House

5 out of 5 average rating, 65 reviews

The exterior of the cottage is shown, featuring a white siding and multiple windows that invite natural light. A well-kept green lawn surrounds the building, complemented by mature trees in the background. The peaceful setting is enhanced by the clear sky.

Guesthouse in Kerhonkson

Cozy Guesthouse & Healing Vibes

Guesthouse in West Hurley

A panoramic view showcasing the Ashokan Reservoir surrounded by lush greenery. The clear blue sky is dotted with soft clouds, while trees frame the scene, creating a tranquil and peaceful setting.

5 out of 5 average rating, 56 reviews

Unequalled Reservoir Mtn Views-Private, Affordable

4.91 out of 5 average rating, 158 reviews

An open living space is illuminated by natural light from multiple windows, featuring a cozy sofa, wooden coffee table, and a dining area with metal chairs. A spiral staircase leads to a loft space, while a door opens to a private outdoor deck.

Guesthouse in Accord

Tiny Horse Barn

Guesthouse in Callicoon Center

A charming guesthouse exterior features a bright red door, framed by green plants and a welcoming bench. Pathway stones lead to the entrance, while a wooden barn stands in the background, surrounded by lush greenery.

4.98 out of 5 average rating, 65 reviews

Indigo Bunting Farms MilkHouse/Sauna & Cold Plunge

4.89 out of 5 average rating, 153 reviews

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

Cozy Catskills Cottage

Guest house rentals with a washer and dryer

4.99 out of 5 average rating, 84 reviews

A dining area is visible with two black chairs surrounding a glass table. A cozy seating space with a light-colored armchair is situated in the corner, while large glass doors open to a spacious covered patio, surrounded by lush greenery.

Guesthouse in Kerhonkson

Kerhamptons Hideaway in Heart of Hudson Valley

4.99 out of 5 average rating, 195 reviews

A lush green field extends towards the horizon, framed by clusters of trees. The sky is filled with varying shades of clouds, reflecting a soft light from the setting sun. The peaceful rural landscape evokes a sense of tranquility.

Guesthouse in Gardiner

Red Barn Retreat - Shawangunk Mountains Getaway

4.86 out of 5 average rating, 149 reviews

A cozy living area features a comfortably upholstered sofa paired with a stylish armchair. A cowhide rug lies on the warm hardwood floor, while a contemporary side table and a console table provide functional space. Art is displayed on the walls, enhancing the room's decor.

Guesthouse in Saugerties

Private Guesthouse in Saugerties

Guesthouse in East Meredith

A covered patio area features two turquoise chairs and a round table positioned on a wooden deck. A small refrigerator and microwave are visible in the background. A decorative rug adds texture to the space, while a nearby hammock invites relaxation.

4.97 out of 5 average rating, 156 reviews

The Lily Pad

4.97 out of 5 average rating, 111 reviews

A well-maintained outdoor space is framed by wooden fencing and lush greenery. A round table is centered on a wooden deck, accompanied by two folding chairs. Soft lighting from above adds a gentle ambiance, creating an inviting atmosphere for relaxation.

Guesthouse in Windham

Little Bear’s Cottage Great location, cozy & cute

Guesthouse in Mongaup Valley

4.99 out of 5 average rating, 433 reviews

Good Vibes Studio in the Woods

5 out of 5 average rating, 71 reviews

A spacious two-story building features a dark exterior with multiple windows and double garage doors. Surrounding trees provide shade, and a gravel area is visible in front, leading to an open meadow beyond.

Guesthouse in Bloomville

Catskill Treetop Retreat