
Guest house holiday rentals in Shandaken
Find and book unique guest house rentals on Airbnb
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.

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

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.

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.
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

Rustic and Elegant Converted Barn

Hiker’s Haven, a Cozy Cabin above Bashakill Refuge

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

Unequalled Reservoir Mtn Views-Private, Affordable

Tiny Horse Barn

Chic, Private Cabin with Stunning River Views

Cozy Catskills Cottage

Clove Casita on Mohonk Preserve
Guest house rentals with a washing machine and dryer

Red Barn Retreat - Shawangunk Mountains Getaway

Private Guesthouse in Saugerties

The Lily Pad

Little Bear’s Cottage Great location, cozy & cute

Modern & Private Cottage Minutes From Woodstock

Wonderful getaway place in the Catskills!

Good Vibes Studio in the Woods

Eco Cottage in the Woods
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
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Rentals with a hot tub Shandaken
- Flat rentals Shandaken
- Cabin rentals Shandaken
- Rentals with outdoor seating Shandaken
- Pet-friendly rentals Shandaken
- Rentals with beach access Shandaken
- Rentals with breakfast Shandaken
- Fitness-friendly rentals Shandaken
- Rentals with an EV charger Shandaken
- Rentals with a washing machine and dryer Shandaken
- Rentals with a sauna Shandaken
- House rentals Shandaken
- Family-friendly rentals Shandaken
- Rentals with a fireplace Shandaken
- Rentals with lake access Shandaken
- Rentals with pools Shandaken
- Bed and breakfasts Shandaken
- Rentals with a patio Shandaken
- Waterfront rentals Shandaken
- Cottage rentals Shandaken
- Rentals with a firepit Shandaken
- Boutique hotels Shandaken
- Guest house rentals Ulster County
- Guest house rentals New York
- Guest house rentals United States
- 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





