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Shady Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (299 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.
$268 nightly
The price is $300
Sep 28 - Sep 29
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
A modern kitchen with a central island, black cabinetry, and pendant lighting.

2. Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House
Woodstock
10.0 out of 10, Exceptional, (13 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.
$547 nightly
The price is $612
Sep 28 - Sep 29
Total with taxes and fees
Woodstock Historic Artist Estate - The Museum House
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

3. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (314 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
$125 nightly
The price is $140
Sep 28 - Sep 29
Total with taxes and fees
Starlite Motel

4. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (12 reviews)
"Oh, I gave this property excellent scores for all the questions but I am reminded now by the suggestions for what to write about about the fact that it listed an Ocean view, which is obviously a mistake. It’s nowhere near the ocean. There’s no ocean view. It is in the woods it’s secluded.I actually took a very little walk in the middle of the night in the dark using my cell phone flashlight and got kind of lost for a while, but managed to find my way back. That was quite an interesting...
United States
Michael H.
$179 nightly
The price is $200
Sep 29 - Sep 30
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

5. 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, (309 reviews)
"Excellent place"
United States
Yeudin
$201 nightly
The price is $217
Oct 26 - Oct 27
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A bar area with wooden stools, a bar counter, shelves of bottles, a television, and a sign for drink specials.

6. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.8 out of 10, Excellent, (5 reviews)
"cute little spot! very nice place to stay"
United States
David R.
$195 nightly
The price is $207
Sep 29 - Sep 30
Total with taxes and fees
Jessie's Harvest House
A dining room with a wooden table, four chairs, a chandelier, a window with a view, and a wooden cabinet with glass doors.

7. Country House offers 2 bedrooms and a den, lots of parking.

Country House offers 2 bedrooms and a den, lots of parking.
Saugerties
$305 nightly
The price is $342
Sep 28 - Sep 29
Total with taxes and fees
Country House offers 2 bedrooms and a den, lots of parking.
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, (36 reviews)
"loved our stay and would stay again!"
United States
MIKE W.
$176 nightly
The price is $197
Oct 5 - Oct 6
Total with taxes and fees
West Wing - a unique private space w/patio
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

9. 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, (103 reviews)
"Wonderful stay. "
United States
Chris L.
$231 nightly
The price is $259
Sep 28 - Sep 29
Total with taxes and fees
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

10. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
$230 nightly
The price is $258
Sep 28 - Sep 29
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
A bar area with wooden stools, a bar counter, shelves of bottles, a television, and a sign for drink specials.

11. Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
9.0 out of 10, Wonderful, (8 reviews)
"Everything's done online and great food within mins from the stay. Very accommodating and pet friendly! Super easy to communicate and fast response no matter the time! "
United States
Jennie D.
$164 nightly
The price is $173
Sep 28 - Sep 29
Total with taxes and fees
Jessie's Harvest House Suite
A log cabin with a porch, a staircase, and a garage.

12. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.4 out of 10, Exceptional, (34 reviews)
"Loved how secluded it was ,the quietness the unit was exceptional clean & fresh , The grounds are expertly groomed with a ,firepit and a really nice hot tub will be back again as a 3 &4 bedroom unit is availiblealso"
United States
alain
$200 nightly
The price is $216
Sep 28 - Sep 29
Total with taxes and fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
A bar area with wooden stools, a bar counter, shelves of bottles, a television, and a sign for drink specials.

13. Jessie's Harvest House

Jessie's Harvest House
Tannersville
$195 nightly
The price is $207
Sep 29 - Sep 30
Total with taxes and fees
Jessie's Harvest House
A two-story house with a covered porch and a small deck.

14. Stylish Studio on Main Street in Tannersville

Stylish Studio on Main Street 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.
$199 nightly
The price is $215
Sep 28 - Sep 29
Total with taxes and fees
Stylish Studio on Main Street in Tannersville
A forested landscape with a wooden structure in the foreground.

15. Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (33 reviews)
"Excellent stay"
United States
Laura S.
$323 nightly
The price is $348
Sep 28 - Sep 29
Total with taxes and fees
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
An outdoor deck with a table and chairs, surrounded by trees and a wood-burning stove.

16. 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.
$639 nightly
The price is $716
Sep 28 - Sep 29
Total with taxes and fees
Cozy Mid-Century Retreat with Spa Hot Tub
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, (40 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.
$320 nightly
The price is $359
Sep 28 - Sep 29
Total with taxes and fees
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
A house with a front porch, a red door, and a small balcony.

18. 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.
$218 nightly
The price is $235
Sep 28 - Sep 29
Total with taxes and fees
Tannersville 1BR on Main Street, sleeps 3
A fireplace with a stone wall, a stack of firewood, and a bookshelf with books.

19. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.8 out of 10, Exceptional, (21 reviews)
"The property was just as described, very private and cozy. We enjoyed the large balcony as well as the yard. There were also several nice hiking trails close by. Overall we were very happy with our stay."
United States
Ryan P.
$268 nightly
The price is $289
Sep 28 - Sep 29
Total with taxes and fees
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A hanging flower basket with purple and white flowers, a white fence, and a green lawn in the background.

20. Elegant Studio on Tannersville Main Street

Elegant Studio on Tannersville Main Street
Tannersville
10.0 out of 10, Exceptional, (19 reviews)
"Great location."
United States
Edward P.
$203 nightly
The price is $220
Sep 28 - Sep 29
Total with taxes and fees
Elegant Studio on Tannersville Main Street
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

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

8/10 Good
"Just for starters, our room was very very clean and very nice. Lots of room comfortable, bed. I guess some of the problems were with the outside areas. We noticed outside our patio, a pile of cigarette butts and roaches, and some chipping paint that didn’t appear to have been cleaned up for a while. We arrived on a Tuesday afternoon, though the front desk staff were friendly, just didn’t seem to be overly motivated to accommodate new guests. One of the highlights is the outdoor fire pit, which has a really lovely setting. However, the fire pit was filled with trash that appeared to be pill packages and I’m taking a LOT of them! They weren’t cleaned out, just kind of shoved to the side, we had to ask them the next day if they could clean out the fire pit which they did fairly well. Definitely noticed somewhere and tear on the outside such as chipped and peeling paint on these patios and stairways. Overall, a nice day could just use a little facelift!"
Celia 3-night trip
Posted 9 hours ago
Hunter Lodge, a Bluebird by Lark

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 $140 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?

Catskill Cottage Walk to Downtown & River Views: You might want to consider this vacation home rental near Shady, which offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.