
Guest house holiday rentals in Shandaken
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Top-rated guest house rentals in Shandaken
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

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.

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!

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

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.

Private Cottage, Walk to Restaurants and Shops
Beautifully renovated modern cottage in the village of Red Hook has modern amenities, hardwood floors, and an open floor plan. The cooks kitchen has an island and high-end appliances. Walls of windows and doors bring in lots of light and there's a private patio out back. Bathroom has large walk-in shower. Bedroom has a king bed (or two twins) and a recliner for reading. A 3 minute walk from center of Red Hook and Bard Shuttle. 10 minute drive to both Bard College and Rhinebeck.

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.

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.

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!

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.

Creekside Cottage in the heart of Phoenicia
“Nestled in the heart of the high peaks region of the Catskill Mountains.” Cozy creekside cottage located on Phoenicia’s iconic Main Street Walk to hiking, shopping and dining. Plush queen bed, convertible sofa bed, full kitchen and more. Inquire about meal prep, private dinners and fridge stocking with fresh local foods! Come enjoy all that The Catskills has to offer!
Popular amenities for guest house rentals in Shandaken
Family-friendly guest house rentals

Teahouse Cottage by the River.

Game House in Historic Accord

Hudson Valley Hideaway | Cozy Loft Near Rhinebeck

Charming 1 Bedroom Guest Cottage

Little Bliss Pond House

Cozy Mountainside Suite - Minutes from Beacon

Cottage on Coddington Lane,

Indigo Bunting Farms MilkHouse/Sauna & Cold Plunge
Guest house rentals with a patio

Kerhamptons Hideaway in Heart of Hudson Valley

Cozy Cottage with View Mountain-Ashokan Reservoir

R52Creekside one bedroom cottage

Hiker’s Haven, a Cozy Cabin above Bashakill Refuge

Modern & Private Cottage Minutes From Woodstock

Unequalled Reservoir Mtn Views-Private, Affordable

Tiny Horse Barn

Chic, Private Cabin with Stunning River Views
Guest house rentals with a washing machine and dryer

Red Barn Retreat - Shawangunk Mountains Getaway

Private Guesthouse in Saugerties

The Lily Pad

The Lily Cottage Guesthouse

Little Bear’s Cottage Great location, cozy & cute

Wonderful getaway place in the Catskills!

Eco Cottage in the Woods

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star
When is the best time to visit Shandaken?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £148 | £150 | £149 | £118 | £136 | £142 | £150 | £144 | £153 | £149 | £144 | £148 |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
Quick stats about guest house rentals in Shandaken

Total holiday rentals
Explore 30 holiday rentals in Shandaken

Nightly prices starting at
Shandaken holiday rentals start at £60 per night before taxes and fees

Verified guest reviews
Over 1,120 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Shandaken holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shandaken rentals

4.5 Average rating
Shandaken stays receive an average rating of 4.5 out of 5 from guests
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Minnewaska State Park Preserve
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Howe Caverns
- Windham Mountain
- Plattekill Mountain
- Bash Bish Falls State Park
- Thacher State Park
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Hunter Mountain Resort
- Taconic State Park
- Walkway Over the Hudson State Historic Park
- Storm King Art Center
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Benmarl Winery
- Poets' Walk Park
- Opus 40
- Mohonk Preserve
- Ranch Skydive





