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Shady Vacation Rentals

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Check prices for these dates

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

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.
$291 nightly
The price is $326
Nov 10 - Nov 11
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

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
$201 nightly
The price is $217
Nov 19 - Nov 20
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A building with a large window reflecting trees, a wooden exterior, and a yellow roof.

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.
$440 nightly
The price is $487
Oct 21 - Oct 22
Total with taxes and fees
A pleasant space in a pleasant neighborhood in a beautiful part of the country!
A modern kitchen with a large island, a sink, and wooden stools.

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.
$532 nightly
The price is $596
Oct 26 - Oct 27
Total with taxes and fees
Woodstock Historic Artist Estate - The Carriage House
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

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
$145 nightly
The price is $162
Oct 21 - Oct 22
Total with taxes and fees
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.

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
$223 nightly
The price is $249
Nov 9 - Nov 10
Total with taxes and fees
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A modern kitchen with a central island, black cabinetry, and pendant lighting.

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.
$570 nightly
The price is $638
Oct 21 - Oct 22
Total with taxes and fees
Woodstock Historic Artist Estate - The Museum House
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.
$180 nightly
The price is $202
Oct 22 - Oct 23
Total with taxes and fees
West Wing - a unique private space w/patio
An outdoor deck with a table and chairs, surrounded by trees and a wood-burning stove.

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.
Cozy Mid-Century Retreat with Spa Hot Tub
A forested landscape with a wooden structure in the foreground.

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.
$342 nightly
The price is $369
Oct 21 - Oct 22
Total with taxes and fees
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Private kitchen

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
$181 nightly
The price is $203
Oct 22 - Oct 23
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
A cozy living room with a green sofa, a coffee table, a fireplace, and a bookshelf.

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.
$800 nightly
The price is $903
Oct 21 - Oct 22
Total with taxes and fees
Hot Tub * Fireplace * Near Woodstock
A two-story house with a covered porch and a small deck.

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.
$202 nightly
The price is $218
Oct 22 - Oct 23
Total with taxes and fees
Modern Main Street Studio in Tannersville
A residential area with a main road, houses, and a lake.

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.
$190 nightly
The price is $201
Oct 25 - Oct 26
Total with taxes and fees
Jessie's Harvest House
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
$450 nightly
The price is $504
Oct 21 - Oct 22
Total with taxes and fees
Umana's Cabin, cozy, comfy, 5+ acres of land
A tented area with two wooden folding chairs and a table, a patterned rug, and a view of greenery and a white tent in the background.

16. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
$227 nightly
The price is $254
Oct 26 - Oct 27
Total with taxes and fees
Gatherwild Ranch
A room with a wooden cabinet, a glass door leading to a closet, a blue patterned rug, and a wooden floor.

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.
$341 nightly
The price is $382
Oct 26 - Oct 27
Total with taxes and fees
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
A hot tub in a natural setting with a tree and a body of water.

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.
$360 nightly
The price is $403
Oct 21 - Oct 22
Total with taxes and fees
Peaceful Riverfront Cottage with Private Hot tub
A house with a front porch, a red door, and a small balcony.

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.
$227 nightly
The price is $246
Oct 21 - Oct 22
Total with taxes and fees
Tannersville 1BR on Main Street, sleeps 3
A living room with a stone fireplace, leather sofa, and a mounted TV displaying 'NETFLIX'.

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.
$212 nightly
The price is $230
Nov 4 - Nov 5
Total with taxes and fees
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

Kingston Regency Inn

Kingston Regency Inn

8/10 Good
"Room was clean on arrival. Staff very friendly and helpful."
Kimberley 3-night trip
Posted less than an hour ago
Kingston Regency Inn

Find out more about Shady

Everything you need to know about Shady vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shady vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Shady vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shady vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $162 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shady rentals

At Expedia, we put the best Shady vacation 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 Shady 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 Shady vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shady. 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 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.