Shandaken Holiday Rentals

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Holiday Rentals in Shandaken

Cottage in Woodstock

10.0 out of 10, Exceptional, (261)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
The price is NZ$671
includes taxes & fees
13 Dec - 14 Dec
Streamside Cottage Half Mile to Town of Woodstock

Aparthotel in Big Indian

2.5 star property
9.2 out of 10, Wonderful, (273)
"Awesome place to stay!"
United States
Earl
The price is NZ$240
includes taxes & fees
5 Jan - 6 Jan 2026
Starlite Motel

Holiday Home in Kingston

9.8 out of 10, Exceptional, (62)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
United States
Rebecca
The price is NZ$456
includes taxes & fees
11 Dec - 12 Dec
Esopus Creek modern Tiny house Retreat!

Chalet in Fleischmanns

10.0 out of 10, Exceptional, (131)
"Absolutely fabulous place we stayed for my daughter’s wedding. "
United States
Robert Joseph J.
Stunning Catskills Cabin Getaway, facing BelleAyre

Chalet in Fleischmanns

9.6 out of 10, Exceptional, (63)
"Nice place. Enjoyed the hot tub. Good restaurant down the road. Just what we needed. "
United States
john C.
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

Holiday Home in West Kill

9.8 out of 10, Exceptional, (151)
"This is a fantastic place- lots of space and beautiful. Really enjoyed the hot tub"
United States
Evan S.
Catskill Mountain Getaway - minutes to Hunter, Windham and Belleayre Skiing

Cabin in Saugerties

8.2 out of 10, Very good, (46)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
The price is NZ$281
includes taxes & fees
17 Dec - 18 Dec
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Holiday Home in Bearsville

10.0 out of 10, Exceptional, (124)
"A beautiful house on a stunning property. Looking forward to coming back!"
United States
A. M.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Cottage in West Shokan

10.0 out of 10, Exceptional, (54)
"Wonderful experience and beautiful property."
United States
James B.
Relaxing Catskill Mountain Cottage.

Cottage in woodstock

9.0 out of 10, Wonderful, (45)
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. "
United States
Shannon F.
The price is NZ$543
includes taxes & fees
7 Dec - 8 Dec
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Holiday Home in City Roxbury

9.4 out of 10, Exceptional, (30)
"Beautiful house, clean and in a beautiful location. A perfect home for rest and enjoyment in nature"
United States
Janko S.
The price is NZ$1,247
includes taxes & fees
3 Jan - 4 Jan 2026
A world where time stands still, close to Belleayre Ski & Wedding venues.

Apartment in Saugerties

9.8 out of 10, Exceptional, (95)
"Enjoyed our stay!"
United States
Mike T.
A Spectacular 50 Mile View of the Hudson Valley in all seasons

Cabin in Hunter

10.0 out of 10, Exceptional, (271)
"House was great. Plenty of beds, great kitchen and large table for all. Kitchen was well stocked. "
United States
Sarah A.
The price is NZ$1,650
includes taxes & fees
8 Dec - 9 Dec
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

Holiday Home in hunter

9.6 out of 10, Exceptional, (138)
"Really beautiful location with plenty of bedrooms. Very clean!"
United States
Ellen B.
Beautiful new house 3/4 mile from Hunter Mountain

Cabin in Grahamsville

9.4 out of 10, Exceptional, (36)
"House was great! Very clean, loved the outdoor space with the hammock! Would definitely stay here again. "
United States
Kevin D.
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly

Holiday Home in Prattsville

9.8 out of 10, Exceptional, (87)
"Lovely cozy spot with plenty to do inside and out. "
United States
Zachary W.
Private Waterfront on 6 Acres w/Hot Tub.Fire Pit.Views. Hiking.Games.

Holiday Home in Hunter

9.6 out of 10, Exceptional, (51)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
United States
Chris S.
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

Cabin in Hobart

9.6 out of 10, Exceptional, (98)
"Adorable cabin in a beautiful area. Perfect for a weekend getaway !!"
United States
Teresa M.
Mountain Top Retreat, 116 private acres

Holiday Home in Andes

9.8 out of 10, Exceptional, (168)
"We enjoyed our stay and hope to visit again"
United States
Oren S.
Tranquil Paradise With Lake And Catskill Mountain Views

Holiday Home in Windham

9.8 out of 10, Exceptional, (31)
"Excellent! The host was super friendly, helpful and was an excellent communicator. We had a great time!"
United States
Ray L.
A'Neils Windham Ski Lodge & Family Retreat
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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Top Shandaken Hotel Reviews

Find out more about Shandaken

Everything you need to know about Shandaken holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shandaken holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shandaken holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shandaken holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shandaken. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shandaken holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shandaken holiday rentals we have selected for you start as low as NZ$240 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shandaken rentals

At Expedia, we put the best Shandaken holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Shandaken rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shandaken holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shandaken. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat: This holiday home rental outside of Shandaken is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Shandaken?

With 10 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.

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.