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Shady Holiday Rentals

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Check prices for these dates

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

Our top choices for Shady holiday 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, (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 traveller
The price is HK$1,122
HK$2,415 total
includes taxes & fees
7 Sept - 8 Sept
Streamside Cottage Half Mile to Town of Woodstock
An open deck with potted plants, a table, and a chair.

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.
The price is HK$1,411
HK$2,449 total
includes taxes & fees
8 Sept - 9 Sept
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

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.
The price is HK$541
HK$1,949 total
includes taxes & fees
31 Aug - 1 Sept
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A modern kitchen with a central island, black cabinetry, and pendant lighting.

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.
The price is HK$4,773
HK$8,112 total
includes taxes & fees
8 Sept - 9 Sept
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.

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
The price is HK$980
HK$1,097 total
includes taxes & fees
2 Sept - 3 Sept
Starlite Motel
An outdoor deck with a table and chairs, surrounded by trees and a wood-burning stove.

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.
The price is HK$3,566
HK$7,076 total
includes taxes & fees
3 Sept - 4 Sept
Cozy Mid-Century Retreat with Spa Hot Tub
A cabin with a deck, outdoor seating, and a large window.

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.
Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

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
The price is HK$1,373
HK$3,801 total
includes taxes & fees
30 Aug - 31 Aug
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
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, (99 reviews)
"Convenient and comfortable stay"
United States
Cathy G.
The price is HK$1,340
HK$2,107 total
includes taxes & fees
23 Sept - 24 Sept
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

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, (286 reviews)
"Loved my stay at the little cabin, will definitely be returning."
United States
Rosemary
The price is HK$1,325
HK$1,769 total
includes taxes & fees
9 Sept - 10 Sept
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A rustic cabin with a wooden deck and a chair, surrounded by dense forest.

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.
The price is HK$882
HK$1,163 total
includes taxes & fees
30 Aug - 31 Aug
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

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
The price is HK$894
HK$1,598 total
includes taxes & fees
30 Aug - 31 Aug
Woods Cabin-Kingston/Woodstock, NY.
A wooden deck with a bench, surrounded by a forested area.

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
The price is HK$988
HK$1,571 total
includes taxes & fees
31 Aug - 1 Sept
West Wing - a unique private space w/patio
A covered porch with a wooden deck, white columns, wicker chairs, and a view of a house with windows.

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.
The price is HK$670
HK$1,276 total
includes taxes & fees
15 Sept - 16 Sept
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
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.

15. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is HK$1,940
HK$2,173 total
includes taxes & fees
1 Sept - 2 Sept
Gatherwild Ranch
A log cabin interior with a large gray sectional sofa, a wooden coffee table, and a dining area with a kitchen in the background.

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.
The price is HK$2,195
HK$4,732 total
includes taxes & fees
23 Sept - 24 Sept
Cozy Log Cabin with Hot-Tub, Firepit & Prime Catskills Location
A forested landscape with a wooden structure in the foreground.

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.
The price is HK$1,587
HK$2,925 total
includes taxes & fees
31 Aug - 1 Sept
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
A spacious living room with a large sectional sofa, a chandelier, and a sign indicating 'SLOPES'.

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.
The price is HK$5,479
HK$9,168 total
includes taxes & fees
31 Aug - 1 Sept
LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED
A two-story building with large windows and a storefront.

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.
The price is HK$666
HK$1,143 total
includes taxes & fees
8 Sept - 9 Sept
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

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.
The price is HK$682
HK$2,133 total
includes taxes & fees
23 Sept - 24 Sept
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

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"good facility"
Andrea 1-night trip
Posted 13 hours ago
Howard Johnson by Wyndham Saugerties

Find out more about Shady

Search for holiday rentals in Shady on Expedia! You can easily find your home rentals, villas, holiday apartments in Shady using one of the methods below:

  • View our selection of featured holiday rentals in Shady
  • Use the map to find apartments and other holiday homes in the Shady neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shady while they last

Look no further and take a look at our great range of rental properties in Shady!

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?

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!: This holiday home rental outside of Shady is located on a river, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family.

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 Karma Triyana Dharmachakra Monastery and Bearsville Theater.

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.