Guest house holiday rentals in Shandaken

Cozy Hillside Hideaway with Hot Tub

Enjoy the peace and quiet of the Catskills with easy access to all that mid Hudson valley has to offer. 5 minutes to Uptown Kingston and the O&W and Wallkill rail trails; 15-25 minutes to Rhinebeck, Ashokan Reservoir, Woodstock, Saugerties and New Paltz; 30-45 minutes to Lake Minnewaska, Mohonk Mtn House, Belleayre, Hunter and Wyndham. Also close to a number of wedding venues (Hasbrouck House, Senate Garage, Hutton Brickyards…). Guest apt is attached to our home but you have a private entrance.

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

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

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.

Sunny Arts & Crafts Loft

Warmer days are here. Hiking, biking, swimming, fishing, golf among your great Catskill Mtn. options! Or, just relax by the fire pit. Some great summer dates still available. Never too early to plan for fall. Explore fun towns like Margaretville & Andes. Cooling mountain breezes provide AC - with a boost from a ceiling fan and portable fans. The Loft is a cozy, private spot to unwind in a peaceful mountainside location. Super savings on longer stays! Lots to do! Or do nothing at all!

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.

Private lofted retreat with Steam room HotTub/Pool

Take it easy at this unique and tranquil getaway. off NYS thruway close to local restaurants/shops 5 min from town of Saugerties & Hits 25 min from Hunter Mt Skiing 15 min from town of Woodstock and close to hiking trails Relax in the New hot tub on private outdoor deck reset yourself in the 2 person custom steam room also a Salt water inground pool available King size bed in loft and pull out full mattress in sectional couch just renovated with all new furniture full kitchen

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.

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 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.

R52Creekside one bedroom cottage

NEW Construction! Centrally located to all Sullivan county has to offer! Bethel woods, Livingston Manor, Callicoon and much more close by! Walk to a great little local deli and drive to many close restaurants. Set up for two adults or two adults with one small child. Efficiency kitchen (no oven). Ten acres with a creek and lots of area to walk and have a dog. King bed sleeping loft! Great area to explore in summer and winter! Dogs welcome!

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.

Stylish Woodstock Guest House..Mountain View

This 1920's converted barn has the original beams and antique fixtures w/vintage and new furnishings. The french doors on one complete wall amplify the open space with views of the Catskill Mts., pond, fields, and the vast sky. No smoking no pets. You love them, I love them, but they cannot stay here. Also, two night minimum stay. Three night minimum on holiday weekends.