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Shady Holiday Rentals

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Our top choices for Shady holiday rentals

1. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (305 reviews)
"It was the perfect place for a weekend away from home! The location was only a few minutes from town and was the perfect size for a couple. Would definitely reccomend!"
United States
Kristen S.
The price is NZ$564
includes taxes & fees
10 Nov - 11 Nov
Streamside Cottage Half Mile to Town of Woodstock

2. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (325 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
The price is NZ$366
includes taxes & fees
18 Nov - 19 Nov
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

3. A pleasant space in a pleasant neighborhood in a beautiful part of the country!

A pleasant space in a pleasant neighborhood in a beautiful part of the country!
Woodstock
10.0 out of 10, Exceptional, (9 reviews)
"Very nice property that met our needs perfectly. Clean and very well maintained rooms. Lots of wildlife, beautiful wooded area. Peter, the host, was lovely and helpful."
United States
Barbara A.
The price is NZ$837
includes taxes & fees
21 Oct - 22 Oct
A pleasant space in a pleasant neighborhood in a beautiful part of the country!

4. Woodstock Historic Artist Estate - The Carriage House

Woodstock Historic Artist Estate - The Carriage House
Woodstock
9.8 out of 10, Exceptional, (50 reviews)
"We had a wonderful time, again! Perfect location!"
United States
Fran W.
The price is NZ$1,056
includes taxes & fees
26 Oct - 27 Oct
Woodstock Historic Artist Estate - The Carriage House

5. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (320 reviews)
"The special game room in the back yard that is screened is excellent 👌."
United States
Stephen
The price is NZ$287
includes taxes & fees
16 Nov - 17 Nov
Starlite Motel

6. Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Kingston
9.6 out of 10, Exceptional, (106 reviews)
"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"
United States
Nan
The price is NZ$433
includes taxes & fees
9 Nov - 10 Nov
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

7. Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House
Woodstock
9.8 out of 10, Exceptional, (14 reviews)
"We had a short stay but absolutely loved the house. Perfect location, lots of space, and the hosts were great. Would stay again, highly recommend!"
United States
Strati P.
The price is NZ$1,091
includes taxes & fees
21 Oct - 22 Oct
Woodstock Historic Artist Estate - The Museum House

8. West Wing - a unique private space w/patio

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (37 reviews)
"loved our stay and would stay again!"
United States
MIKE W.
The price is NZ$353
includes taxes & fees
28 Oct - 29 Oct
West Wing - a unique private space w/patio

9. Cozy Mid-Century Retreat with Spa Hot Tub

Cozy Mid-Century Retreat with Spa Hot Tub
Woodstock
10.0 out of 10, Exceptional, (13 reviews)
"Great spot, close to town but removed enough to have total privacy. Thank you!"
United States
Alec M.
The price is NZ$1,278
includes taxes & fees
21 Oct - 22 Oct
Cozy Mid-Century Retreat with Spa Hot Tub

10. Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (34 reviews)
"Excellent stay"
United States
Laura S.
The price is NZ$633
includes taxes & fees
21 Oct - 22 Oct
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

11. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (15 reviews)
"Thank you. What an experience!"
United States
Burc
The price is NZ$355
includes taxes & fees
21 Oct - 22 Oct
Woods Cabin-Kingston/Woodstock, NY.

12. Hot Tub * Fireplace * Near Woodstock

Hot Tub * Fireplace * Near Woodstock
Saugerties
10.0 out of 10, Exceptional, (1 review)
"Perfect spot in Saugerties/Woodstock area. Very helpful communication with property management. Looking forward to staying again sometime!"
United States
Theodore F. L.
The price is NZ$1,434
includes taxes & fees
21 Oct - 22 Oct
Hot Tub * Fireplace * Near Woodstock

13. Modern Main Street Studio in Tannersville

Modern Main Street Studio in Tannersville
Tannersville
10.0 out of 10, Exceptional, (8 reviews)
"The place is clean, well maintained, easy to find and right in town by the main road."
United States
Mohamed H.
The price is NZ$403
includes taxes & fees
18 Nov - 19 Nov
Modern Main Street Studio in Tannersville

14. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.4 out of 10, Very good, (7 reviews)
"cute little spot! very nice place to stay"
United States
David R.
The price is NZ$351
includes taxes & fees
17 Nov - 18 Nov
Jessie's Harvest House

15. Umana's Cabin, cozy, comfy, 5+ acres of land

Umana's Cabin, cozy, comfy, 5+ acres of land
Saugerties
9.2 out of 10, Wonderful, (10 reviews)
"Secluded and private but just a short drive away from a little town with great bars, restaurants and music venues. "
United States
Paul
The price is NZ$866
includes taxes & fees
21 Oct - 22 Oct
Umana's Cabin, cozy, comfy, 5+ acres of land

16. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is NZ$480
includes taxes & fees
28 Oct - 29 Oct
Gatherwild Ranch

17. 1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Phoenicia
9.2 out of 10, Wonderful, (41 reviews)
"Such a spectacular and unique home- we loved the thoughtful touches placed throughout the house. Beds comfy, kitchen had everything you could need plus more. Easy walking access to great hiking! The front porch is a perfect place to have morning coffee and watch the rabbits!"
United States
joan b.
The price is NZ$626
includes taxes & fees
2 Nov - 3 Nov
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

18. Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub
Lake Katrine
10.0 out of 10, Exceptional, (17 reviews)
"A nice relaxing spot."
United States
Darren F.
The price is NZ$690
includes taxes & fees
21 Oct - 22 Oct
Peaceful Riverfront Cottage with Private Hot tub

19. Tannersville 1BR on Main Street, sleeps 3

Tannersville 1BR on Main Street, sleeps 3
Tannersville
9.6 out of 10, Exceptional, (16 reviews)
"Great place, great location, great host."
United States
Ed P.
The price is NZ$469
includes taxes & fees
21 Oct - 22 Oct
Tannersville 1BR on Main Street, sleeps 3

20. Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Relax!

Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Relax!
Hunter Highlands
10.0 out of 10, Exceptional, (23 reviews)
"You will definitely return this place is cozy, clean and convenient! "
United States
Elizabeth C.
The price is NZ$483
includes taxes & fees
17 Nov - 18 Nov
Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Relax!
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 Shady Hotel Reviews

Find out more about Shady

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Shady holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Shady. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Shady. Seeing all the best attractions is bound to make you fall in love with Shady. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Shady short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Shady?

Yes, there are holiday rentals close to the most popular sights in Shady, or you can select a more secluded option if you're looking for a relaxing stay.

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

Modern Luxurious Cabin, Catskills - The Tiny Nook: This holiday home rental outside of Shady is located in a rural location, and offers a patio, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Shady?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Shady stay.

What can I see and do in Shady?

Explore the area and family-friendly sights such as Hudson River Maritime Museum, or get out into nature at a spot like Overlook Mountain Trailhead. In the wider area, you’ll find Indian Head Mountain and Ashokan Rail Trail- Woodstock Dike Trailhead.

What are holiday rentals like in Shady?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shady. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family getaway.