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Shady Vacation Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Shady vacation rentals

A natural setting with a stream, red chairs, and a forested area.

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 AED 559
AED 1,197 total
includes taxes & fees
10 Nov - 11 Nov
Streamside Cottage Half Mile to Town of Woodstock
A modern kitchen with a large island, a sink, and wooden stools.

2. 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 AED 995
AED 2,188 total
includes taxes & fees
27 Oct - 28 Oct
Woodstock Historic Artist Estate - The Carriage House
A modern kitchen with a central island, black cabinetry, and pendant lighting.

3. 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 AED 1,678
AED 3,051 total
includes taxes & fees
25 Oct - 26 Oct
Woodstock Historic Artist Estate - The Museum House
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

4. 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 AED 591
AED 797 total
includes taxes & fees
19 Nov - 20 Nov
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A building with a large window reflecting trees, a wooden exterior, and a yellow roof.

5. 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 AED 882
AED 1,800 total
includes taxes & fees
28 Oct - 29 Oct
A pleasant space in a pleasant neighborhood in a beautiful part of the country!
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

6. 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 AED 533
AED 597 total
includes taxes & fees
22 Oct - 23 Oct
Starlite Motel
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

7. 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, (107 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 AED 576
AED 916 total
includes taxes & fees
9 Nov - 10 Nov
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A wooden deck with a bench, surrounded by a forested area.

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 AED 463
AED 740 total
includes taxes & fees
22 Oct - 23 Oct
West Wing - a unique private space w/patio
A bedroom with a large window, a bed, a lamp, and a view of a park.

9. Woodstock historic artist estate - The Pond House

Woodstock historic artist estate - The Pond House
Woodstock
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful host, outstanding location, very nice and creative home. We very much enjoyed our stay, and look forward to coming back again!"
United States
Joe V.
The price is AED 2,116
AED 3,612 total
includes taxes & fees
1 Nov - 2 Nov
Woodstock historic artist estate - The Pond House
Private kitchen

10. 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 AED 419
AED 745 total
includes taxes & fees
22 Oct - 23 Oct
Woods Cabin-Kingston/Woodstock, NY.
A forested landscape with a wooden structure in the foreground.

11. 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 AED 744
AED 1,355 total
includes taxes & fees
22 Oct - 23 Oct
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
A two-story house with a covered porch and a small deck.

12. 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 AED 399
AED 800 total
includes taxes & fees
22 Oct - 23 Oct
Modern Main Street Studio in Tannersville
A bedroom with a large window, wooden ceiling, and a bed with white bedding and two decorative pillows.

13. PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC

PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
Mt. Tremper
9.8 out of 10, Exceptional, (17 reviews)
"Wonderful spot to unwind and take a relaxing getaway."
United States
cheryll s.
The price is AED 694
AED 1,526 total
includes taxes & fees
8 Nov - 9 Nov
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
A cozy living room with a green sofa, a coffee table, a fireplace, and a bookshelf.

14. 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 AED 1,406
AED 3,458 total
includes taxes & fees
27 Oct - 28 Oct
Hot Tub * Fireplace * Near Woodstock
An outdoor deck with a wooden deck, a grill, wicker chairs, and a red umbrella.

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 AED 988
AED 1,852 total
includes taxes & fees
22 Oct - 23 Oct
Umana's Cabin, cozy, comfy, 5+ acres of land
Interior

16. Modern Glass House Near Hunter & Woodstock Fireplace, Views, Pet-Friendly

Modern Glass House Near Hunter & Woodstock Fireplace, Views, Pet-Friendly
Elka Park
9.8 out of 10, Exceptional, (9 reviews)
"Really great property, well stocked, beautiful home with incredible grounds. Would stay here again in a heartbeat. The kids couldn't stop saying, " This is the best vacation rental we've ever had"!"
United States
Jamison G.
The price is AED 1,550
AED 3,007 total
includes taxes & fees
27 Oct - 28 Oct
Modern Glass House Near Hunter & Woodstock Fireplace, Views, Pet-Friendly
A hotel lobby with a reception desk, a door marked "EXIT," a clock, and a small table with a chair.

17. 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 AED 433
AED 739 total
includes taxes & fees
25 Oct - 26 Oct
Jessie's Harvest House
A neatly made bed with white linens, a wall-mounted abstract painting, and a bedside lamp.

18. Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
9.0 out of 10, Wonderful, (8 reviews)
"Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer."
United States
Matthew M.
The price is AED 345
AED 636 total
includes taxes & fees
26 Oct - 27 Oct
Jessie's Harvest House Suite
A hanging flower basket with purple and white flowers, a white fence, and a green lawn in the background.

19. Elegant Main Street Studio in Tannersville

Elegant Main Street Studio in Tannersville
Tannersville
10.0 out of 10, Exceptional, (20 reviews)
"Great location."
United States
Edward P.
The price is AED 451
AED 864 total
includes taxes & fees
22 Oct - 23 Oct
Elegant Main Street Studio in Tannersville
A hot tub in a natural setting with a tree and a body of water.

20. 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 AED 878
AED 1,633 total
includes taxes & fees
26 Oct - 27 Oct
Peaceful Riverfront Cottage with Private Hot tub
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

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

10/10 Excellent
"Clean well maintained, beds were comfortable and the room was very clean."
Mary W 1-night trip
Posted 5 hours ago
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Frequently asked questions

Can I find a vacation rental in Shady?

Yes, we give you a choice of vacation rentals near well known local attractions in Shady, or you can choose a more remote option if you want a relaxing place to stay.

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

Modern Luxurious Cabin, Catskills - The Tiny Nook: You might want to consider this vacation home rental near Shady, which 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 vacation rentals are there in Shady?

With 3 Expedia vacation rentals, you're sure 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 larger area, you’ll find Indian Head Mountain and Ashokan Rail Trail- Woodstock Dike Trailhead.

What are vacation rentals like in Shady?

A vacation rental is a private property you can book for a few weeks or just a few days in Shady. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family trip.