Shandaken Holiday Rentals

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Holiday Rentals in Shandaken

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (244)
"Cosy room, clean bathroom, useable kitchen with all useful appliances. Loved the back yard with the fire pit. A little bit of a drive from our home but it was worth the effort. I would come again."
The price is AU$220
includes taxes & fees
25 Nov - 26 Nov
Starlite Motel

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very good, (42)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is AU$226
includes taxes & fees
27 Nov - 28 Nov
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (224)
"Place was a perfect place to unwind. Very clean and Jane was very communicative!"
The price is AU$499
includes taxes & fees
27 Nov - 28 Nov
Streamside Cottage Half Mile to Town of Woodstock

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter

10.0 out of 10, Exceptional, (143)
"A Big House has enough rooms and beds. Had mostly everything needed, and owner able to answer questions and solve problem in time. the backyard and forest would be better view in spring or summber. "
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter

Tuscan Year Round Beauty - Pickleball Court

10.0 out of 10, Exceptional, (97)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court

Cozy Relaxing Retreat in Saugerties, NY

10.0 out of 10, Exceptional, (42)
"Secluded house very quiet surrounding, owner was very quick to respond "
Cozy Relaxing Retreat in Saugerties, NY

Tranquil Paradise With Lake And Catskill Mountain Views

9.8 out of 10, Exceptional, (148)
"This home is just the perfect little getaway. The views are pretty great and with all the sliding glass doors you have that view inside or out on the huge deck. Its very private and quiet but close enough to restaurants and stores."
Tranquil Paradise With Lake And Catskill Mountain Views

Pet-Friendly Cozy Cabin in the Catskills with Cedar Hot Tub

9.2 out of 10, Wonderful, (15)
"We had a great stay here at woodside! The house was clean and cozy. The perfect long weekend stay for us and our dog. "
Pet-Friendly Cozy Cabin in the Catskills with Cedar Hot Tub

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (175)
"This property is amazing and was exactly what I was looking for! We stayed two nights and upon arriving Paul greeted us and was very kind and helpful. The house was clean and everything was as described. We really enjoyed our stay and will come again."
The Cabin at Chichester in the Catskills Mountains

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

10.0 out of 10, Exceptional, (34)
"This house was adorably charming and perfect for a weekend getaway in Woodstock. We loved watching wildlife from the beautiful kitchen windows and the privacy the property provided. Our pup loved the front sun room and keeping an eye on the yard. Thank you for sharing your home!"
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!

10.0 out of 10, Exceptional, (21)
"My friends and I were looking for a place for 8 of us to enjoy the weekend and it was awesome. The house location has one of the most beautiful sights of any VRBO house I've stayed at. Between the incredible audio systems, furniture layout, overall living room aesthetics, and living room windows designed to take advantage of the beautiful view, the interior was ideal for our group. The host was in constant communication with us and gave clear directions for entering and leaving the house. Highly...
High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (39)
"2 nights in a delightful cottage. It is small but delightfully appointed. The highlight was this clean, warm little cottage is perched directly on swft stream. We left the backdoor open at night!"
The price is AU$434
includes taxes & fees
1 Dec - 2 Dec
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains

10.0 out of 10, Exceptional, (203)
"Very comfortab;e and cozy"
Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains

Beautiful, private Property/swimming pond

9.6 out of 10, Exceptional, (69)
"This home was perfect for our Labor Day weekend reunion, with everything we would need, easy use of fire pit, grill, deck and kitchen (but there is no dishwasher). Gisele was great to communicate with. Would definitely go again!"
Beautiful, private Property/swimming pond

Charming Artist's Retreat

9.8 out of 10, Exceptional, (129)
"Escaped Long Island’s noise, traffic and overall stress . Listened to owls, watched birds soaring, kicked up leaves and gazed at the periwinkle colored mountains while perched on a bench. Felt safe enough knowing civilization was near enough, would have liked a landline phone just in case of an emergency "
Charming Artist's Retreat

LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

9.6 out of 10, Exceptional, (45)
"We really enjoyed our stay in Hunter. The house met our needs well for a large family gathering. The hot tub and game room were excellent. Beutiful inside.It is close to shopping and hiking trails in the area. We did a lot of cooking and could have used larger cutting boards and baking/roasting pans. Be aware that the house is right on the main road into Hunter. The pinball machine was frustrating at times because the ball would get stuck.Overall it was a great stay."
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!

9.6 out of 10, Exceptional, (171)
"Everything was just perfect. The house was spacious and had so many wonderful amenities. Location was great, private and quiet. We enjoyed the hot tub under the stars each night to relax from the hiking! Highly recommend. "
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!

HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

9.6 out of 10, Exceptional, (39)
"The house has anything you want . A private house nice town . Quite,"
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim

10.0 out of 10, Exceptional, (212)
"We had a fantastic stay in Valentyna's home. We had a large group of 16 at the home during labor day weekend. We found the house large, clean, updated and had plenty of space. The bedrooms are roomy, the living spaces are even larger than pictured, and the five different outdoor areas are fantastic. The house has every amenity you can ask for. Direct lake access is steps from the house and the house is close to Hunter for the winter months. We had a great time and would happily stay again. "
The price is AU$1,162
includes taxes & fees
25 Nov - 26 Nov
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim

Moonlight Reflections

10.0 out of 10, Exceptional, (88)
"Very good for people on a short vacation."
Moonlight Reflections
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Shandaken you may be interested in

Shandaken Inn

4.0 star property
10.0 out of 10, Exceptional, (222)
"I had always heard about the Catskills, but had never been before now. Found the Shandaken Inn on an internet search, and wasn't sure if it would be all it seemed to be. it was even better! The property was gorgeous, surrounded by inviting peaks; a large open field, with a swimming pool at one end and several independent cottages at the other, offered a great place for our dog and us to amble; a short nature trail, well maintained, connected to an old railroad bed that was nice to stroll. ...
The price is AU$339
includes taxes & fees
25 Nov - 26 Nov
Shandaken Inn

Catskill Seasons Inn

2.5 star property
8.0 out of 10, Very good, (197)
"Lovely find! Quaint and quiet with mountains and trees surroundings. Dining and bar right underneath the rooms with an outdoor area for chairs circling a fire ring. We felt like the only ones there on the weekend. Beautiful fall foliage drive to Phoenicia and Woodstock. "
The price is AU$226
includes taxes & fees
25 Nov - 26 Nov
Catskill Seasons Inn

Howard Johnson by Wyndham Saugerties

2.0 star property
7.4 out of 10, Good, (1005)
"why I return to HJ—easy access from interstate, restaurant next door, rooms are clean and surprisingly quiet."
The price is AU$195
includes taxes & fees
25 Nov - 26 Nov
Howard Johnson by Wyndham Saugerties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Shandaken?

Yes, there are holiday rentals close to the most popular sights in Shandaken, or you can select a more secluded option if you're looking for a relaxing stay. Shandaken is known for its spas and mountain views.

What are some of the best holiday rentals that Shandaken has to offer?

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter: This holiday home rental outside of Shandaken is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Shandaken?

With 13 Expedia holiday rentals, you're guaranteed to find just the right place for your Shandaken stay.

What’s there to see and do in Shandaken?

Catskill Mountains and Esopus Creek are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Hunter Mountain and Belleayre Beach at Pine Hill Lake.

What’s a holiday rental in Shandaken like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shandaken. Holiday rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for family trips.