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Shady Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Shady vacation rentals

Property grounds

1. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (295 reviews)
"Wonderful property with an easy check in and checkout process. The property and surrounding areas are beautiful. We would stay here again. "
United States
Anonymous traveler
$275 nightly
The price is $308
Sep 7 - Sep 8
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
Terrace/patio

2. Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
8.8 out of 10, Excellent, (48 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
$280 nightly
The price is $314
Sep 7 - Sep 8
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Coffee/tea maker, fridge, microwave, oven

3. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
$222 nightly
The price is $249
Aug 31 - Sep 1
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Interior

4. Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House
Woodstock
10.0 out of 10, Exceptional, (12 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.
$924 nightly
The price is $1,035
Sep 8 - Sep 9
Total with taxes and fees
Woodstock Historic Artist Estate - The Museum House
Premium House, Kitchen, Mountain View | Private kitchen | Coffee/tea maker, full-size fridge, microwave

5. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (311 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
$125 nightly
The price is $140
Aug 27 - Aug 28
Total with taxes and fees
Starlite Motel
Outdoor dining

6. 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)
"We loved the place - beautiful house and setting."
United States
Michele P.
$806 nightly
The price is $903
Sep 3 - Sep 4
Total with taxes and fees
Cozy Mid-Century Retreat with Spa Hot Tub
Terrace/patio

7. Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!

Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!
Hurley
9.4 out of 10, Exceptional, (29 reviews)
"Very family friendly, lots of activities"
United States
Janice B.
$390 nightly
The price is $437
Aug 27 - Aug 28
Total with taxes and fees
Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!
Dining

8. Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Lanesville
9.8 out of 10, Exceptional, (18 reviews)
"This was a beautiful little spot and had everything! We loved our 3 night stay."
United States
Holly
$480 nightly
The price is $485
Aug 30 - Aug 31
Total with taxes and fees
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Interior

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, (99 reviews)
"Convenient and comfortable stay"
United States
Cathy G.
$241 nightly
The price is $270
Aug 31 - Sep 1
Total with taxes and fees
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Exterior

10. 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, (284 reviews)
"Loved my stay at the little cabin, will definitely be returning."
United States
Rosemary
$209 nightly
The price is $226
Sep 7 - Sep 8
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior

11. 'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Saugerties
8.2 out of 10, Very Good, (49 reviews)
"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.
$133 nightly
The price is $148
Aug 30 - Aug 31
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Private kitchen

12. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.4 out of 10, Exceptional, (9 reviews)
"The cabin is awesome. Surrounded by forrest you feel like youre the only person in the world. What's even cooler is its off grid but you dont miss a thing. Lights. Music. Bathroom. There were even a couple board games. Outside fire ready to go. Exactly what I was looking for."
United States
Carrie
$182 nightly
The price is $204
Aug 30 - Aug 31
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
Terrace/patio

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

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (29 reviews)
"I enjoyed my stay at this lovely, clean, cozy home."
United States
Taela
$179 nightly
The price is $200
Aug 30 - Aug 31
Total with taxes and fees
West Wing - a unique private space w/patio
Terrace/patio

14. Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Stone Ridge
8.6 out of 10, Excellent, (18 reviews)
"Clean cozy will be staying again"
United States
Michael C.
$159 nightly
The price is $162
Sep 7 - Sep 8
Total with taxes and fees
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Classic Tent, Garden View | Outdoor dining

15. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
$228 nightly
The price is $256
Sep 14 - Sep 15
Total with taxes and fees
Gatherwild Ranch
Smart TV, fireplace

16. Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location

Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location
Boiceville
9.8 out of 10, Exceptional, (11 reviews)
"Great place and very clean. Beds are very comfortable. Would definitely stay here again."
United States
Charles S.
$543 nightly
The price is $608
Sep 22 - Sep 23
Total with taxes and fees
Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location
Property grounds

17. 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.
$346 nightly
The price is $373
Aug 27 - Aug 28
Total with taxes and fees
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Smart TV, fireplace

18. LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED

LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED
Hunter Highlands
10.0 out of 10, Exceptional, (17 reviews)
"Really nice and spacious property in a great location."
United States
Rohan T.
$1,083 nightly
The price is $1,170
Aug 31 - Sep 1
Total with taxes and fees
LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED
Exterior

19. Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
9.2 out of 10, Wonderful, (45 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
$135 nightly
The price is $146
Sep 8 - Sep 9
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Interior

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

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (32 reviews)
"The place was amazing! Very easy check in/out process and the host is very responsive. "
United States
Samuel M.
$243 nightly
The price is $272
Sep 23 - Sep 24
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
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

Super 8 by Wyndham Kingston

Super 8 by Wyndham Kingston

8/10 Good
"This place was clean and very quiet. The staff was helpful and courteous. It needs updating, but overall, it was a good experience."
Gail 7-night trip
Posted 3 hours ago
Super 8 by Wyndham Kingston

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?

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!: Visitors like this Shady vacation home rental. It is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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 Karma Triyana Dharmachakra Monastery and Bearsville Theater.

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.