Shady holiday rentals

We found 583 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Shady to find one that's perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, such as Wi-Fi and cable TV. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Shady

Showing deals for:1 Jan - 8 Jan

Our Sunny Living Room with Wood Stove
Rear Deck, Hot Tub and Screened Porch
A beautiful spot for our comfortable cabin
Open kitchen.
Exceptional
(119 reviews)

Secluded Cabin with Hot Tub - 5 Miles to Woodstock

Bearsville

8% off
AU$4,424
for 7 nights, 1 cabin
AU$632 per night
includes taxes & fees
Secluded Cabin with Hot Tub - 5 Miles to Woodstock
Outdoor dining
Exterior
Living area
Private kitchen
Exceptional
(49 reviews)

Secluded family retreat within minutes of Woodstock village

Saugerties

8% off
AU$5,118
for 7 nights, 1 home
AU$731 per night
includes taxes & fees
Secluded family retreat within minutes of Woodstock village
Interior
Property grounds
Property grounds
Property grounds
Exceptional
(17 reviews)

Hudson Valley’s Private Waterfront Camping Getaway

Lake Katrine

8% off
AU$2,301
for 7 nights, 1 unit
AU$329 per night
includes taxes & fees
Hudson Valley’s Private Waterfront Camping Getaway
Exterior
Your primary entrance will lead you directly in the homes cool kitchen!
Interior
Kitchen comes fully stocked with pots/pans, dishes, silverware, glasses, etc.
Exceptional
(88 reviews)

Featured on MTV ! You Have To See It To Believe It ! Unlike any other !

Haines Falls

9% off
AU$9,352
for 7 nights, 1 home
AU$1,336 per night
includes taxes & fees
Featured on MTV ! You Have To See It To Believe It ! Unlike any other !
Private kitchen
Property grounds
Living area
Exterior detail
Exceptional
(13 reviews)

"Frank Lloyd Wright" Catskills Mountain Yoga-Spa Retreat on 15 Acres

Mount Tremper

12% off
AU$8,885
for 7 nights, 1 home
AU$1,269 per night
includes taxes & fees
"Frank Lloyd Wright" Catskills Mountain Yoga-Spa Retreat on 15 Acres
stay warm & cozy by the fireplace with large screen TV above
Sit stream side and enjoy the beauty of nature and our (seasonal) fire pit
The fall foliage is gorgeous right in "your own" backyard!!
bluestone, more shaded patio with shade garden
Exceptional
(164 reviews)

Sanctuary by the Stream

Phoenicia

13% off
AU$2,927
for 7 nights, 1 home
AU$418 per night
includes taxes & fees
Sanctuary by the Stream
Living area
Exterior
Private kitchen
Property grounds
Exceptional
(10 reviews)

Most Charming, Most quiet place in the Catskills--Willow-brook Cottage

Lake Hill

8% off
AU$3,063
for 7 nights, 1 cabin
AU$438 per night
includes taxes & fees
Most Charming, Most quiet place in the Catskills--Willow-brook Cottage
Exterior
Private kitchen
Great room featuring a wonderful wall of windows
Dining leads from kitchen, open view of living room
Exceptional
(54 reviews)

Private Woodstock Retreat – Heated Pool, Hot Tub & Fireplace on 5 Secluded Acres

Woodstock

12% off
AU$4,935
for 7 nights, 1 home
AU$705 per night
includes taxes & fees
Private Woodstock Retreat – Heated Pool, Hot Tub & Fireplace on 5 Secluded Acres
Large sliders bring nature indoors
Welcome to Bridge House
In winter, stay toasty warm by the fire
Cooking is a breeze in this recently remodeled kitchen
Exceptional
(128 reviews)

Waterfront Mid-century Modern Gem Surround by Forever Wild Land

Willow

8% off
AU$3,556
for 7 nights, 1 home
AU$508 per night
includes taxes & fees
Waterfront Mid-century Modern Gem Surround by Forever Wild Land
Children’s area
Screened-in porch with woodland views, elegant seating & peaceful ambiance.
Interior
Relax in our screened-in porch surrounded by forest views and sounds of nature.
Wonderful
(7 reviews)

Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

Woodstock

16% off
AU$4,074
for 7 nights, 1 cottage
AU$582 per night
includes taxes & fees
Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch
Dining
Property grounds
Living area
Living area
Exceptional
(23 reviews)

Stylish Saugerties Retreat with Hot Tub + Game Room + Theater + Firepit

Saugerties

8% off
AU$6,455
for 7 nights, 1 home
AU$922 per night
includes taxes & fees
Stylish Saugerties Retreat with Hot Tub + Game Room + Theater + Firepit
Terrace/patio
Exterior
Living area
Room
Exceptional
(75 reviews)

Ski on Ski off 4BR Hunter Highlands Condo Super Clean! Big roomy

Hunter

8% off
AU$7,303
for 7 nights, 1 apartment
AU$1,043 per night
includes taxes & fees
Ski on Ski off 4BR Hunter Highlands Condo Super Clean! Big roomy
Entrance to Tannery Brook Cottage in July with Front Porch and Day Lilies
Terraced Rock Garden with Rustic Stone Walls and Massive Steps
Open Plan Kitchen / Dining Area with French Doors and Screen Porch in Distance
Dining Area with Curio Cabinet, Book Shelf and Office Nook with Computer Station
Exceptional
(18 reviews)

Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.

Woodstock

11% off
AU$4,261
for 7 nights, 1 cottage
AU$609 per night
includes taxes & fees
Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.
Third view of LR with woodstove
View #1 of deck with mountain in background
One side of romantic master bedroom with pink chaise and king size bed.
Side view of house and deck
Exceptional
(46 reviews)

Beautiful large Woodland Valley/Phoenicia post & beam cabin with seasonal stream

Phoenicia

8% off
AU$3,436
for 7 nights, 1 home
AU$491 per night
includes taxes & fees
Beautiful large Woodland Valley/Phoenicia post & beam cabin with seasonal stream
Terrace/patio
Steps from craft libations at Early Terrible (pic'd), A&P, The Pub, Station Bar
Living area
Interior
Exceptional
(255 reviews)

Village Center: Gracious & Spacious Retreat "Above the Books"

Woodstock

8% off
AU$2,524
for 7 nights, 1 apartment
AU$361 per night
includes taxes & fees
Village Center: Gracious & Spacious Retreat "Above the Books"
Updated stainless steel kitchen with granite breakfast bar
Dining table area with slider to wrap around deck and stairs to loft
Master bedroom with queen size bed and 65” smart tv
Living room towards dining table and slider to wrap around deck
Exceptional
(38 reviews)

Hunter Mountains Hill Top Hide Away Trail Side

Hunter

8% off
AU$4,769
for 7 nights, 1 apartment
AU$681 per night
includes taxes & fees
Hunter Mountains Hill Top Hide Away Trail Side
Interior
Property grounds
Property grounds
Outdoor dining
Exceptional
(46 reviews)

Peace Cottage

Willow

7% off
AU$2,416
for 7 nights, 1 home
AU$345 per night
includes taxes & fees
Peace Cottage
Dining Room Looking out to Private Lake
Living area
Interior
Property grounds
Exceptional
(28 reviews)

Incredible Lake House with Stunning Mountain Views (swimming lake)

Chichester

8% off
AU$5,615
for 7 nights, 1 home
AU$802 per night
includes taxes & fees
Incredible Lake House with Stunning Mountain Views (swimming lake)
Living area
Dining
Private kitchen
Interior
Exceptional
(27 reviews)

Gorgeous Villa w/ Mountain Views, pool, hot tub!

Glenford

5% off
AU$5,907
for 7 nights, 1 home
AU$844 per night
includes taxes & fees
Gorgeous Villa w/ Mountain Views, pool, hot tub!
Exterior
Terrace/patio
Living area
Private kitchen
Exceptional
(12 reviews)

Charming 2-bedroom cottage with WiFi and AC in fabulous Phoenicia

Phoenicia

8% off
AU$2,402
for 7 nights, 1 cottage
AU$343 per night
includes taxes & fees
Charming 2-bedroom cottage with WiFi and AC in fabulous Phoenicia
Large bedroom overlooking creek
Exterior
Huge back deck overlooking the creek perfect for relaxing and entertaining.
Living room with large dining bar
Exceptional
(13 reviews)

Magical Waterfront Escape from the city located in the Hudson Valley!

Lake Katrine

8% off
AU$4,809
for 7 nights, 1 home
AU$687 per night
includes taxes & fees
Magical Waterfront Escape from the city located in the Hudson Valley!
Interior
Exterior
Living area
Dining
Exceptional
(7 reviews)

Charming 3-bedroom bungalow with AC in Phoenicia, Catskills

Phoenicia

8% off
AU$3,860
for 7 nights, 1 home
AU$551 per night
includes taxes & fees
Charming 3-bedroom bungalow with AC in Phoenicia, Catskills
Interior
Living area
Bathroom
Room
Exceptional
(44 reviews)

Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby

Phoenicia

17% off
AU$1,896
for 7 nights, 1 apartment
AU$271 per night
includes taxes & fees
Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby
Dining
Terrace/patio
Interior
Pool
Exceptional
(14 reviews)

Charming rustic home in the Hudson Valley. Pool is heated and open! New Hot Tub!

Saugerties

11% off
AU$4,562
for 7 nights, 1 home
AU$652 per night
includes taxes & fees
Charming rustic home in the Hudson Valley. Pool is heated and open! New Hot Tub!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Shady getaway

Learn about the unique charm of Shady with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Shady

Do you want to find top things to see and do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Shady has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Indian Head Mountain (5.4 mi / 8.7 km)
  • Hunter Mountain (9.8 mi / 15.8 km)
  • Kaaterskill Falls (9.9 mi / 16 km)
  • Windham Mountain Resort (16.2 mi / 26 km)
  • Woodstock Golf Club (3.3 mi / 5.3 km)
  • Mountain Trails Cross Country Ski and Snowshoe Center (8.8 mi / 14.2 km)

Exploring the natural features in Shady

Whether you're an active traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Shady. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Overlook Mountain Trailhead (1.9 mi / 3 km)
  • Ashokan Rail Trail- Woodstock Dike Trailhead (6.1 mi / 9.9 km)
  • Opus 40 (6.6 mi / 10.6 km)
  • Kaaterskill Falls (9.9 mi / 16 km)
  • Saugerties Village Beach (10.6 mi / 17.1 km)
  • Esopus Creek (11.5 mi / 18.5 km)

How to get to and around Shady

The nearest airport is in Hudson, NY (HCC-Columbia County), located 27.7 mi (44.6 km) from the city centre.

Frequently asked questions

When is the best time to visit Shady for a holiday rental?
September is the most popular time to visit Shady, New York, as summer transitions into autumn, providing a great blend of pleasant weather and stunning scenery. This period, particularly from July to September, draws in travellers seeking to enjoy outdoor activities, including hiking and exploring the picturesque landscapes. With temperatures typically ranging from 15 to 25 degrees Celsius, September offers comfortable conditions for sightseeing and outdoor adventures.During this time, visitors can revel in the vibrant colours of the changing leaves, especially as autumn approaches. The nearby Catskill Mountains present a breathtaking backdrop for leisurely hikes and nature walks, making it an excellent choice for those who appreciate both relaxation and exploration.For those seeking a more budget-friendly option, November is a fantastic month to consider for a holiday rental in Shady. This quieter period allows you to enjoy the area's charm without the hustle and bustle of peak tourist season. You can take advantage of lower rental rates while experiencing the serene beauty of the landscape as it prepares for winter.
What are the top attractions in Shady, New York, United States of America?
In Shady, New York, visitors can enjoy the picturesque natural beauty of the Catskill Mountains. The area is great for outdoor enthusiasts, with attractions like the nearby Kaaterskill Falls, which boasts stunning views and hiking trails. Another highlight is the Hudson River, where opportunities for boating and fishing abound. Shady is also close to the charming town of Woodstock, known for its vibrant arts scene and historic sites. Additionally, the nearby Ashokan Reservoir offers scenic walking paths and picnic areas, ideal for a relaxing day outdoors.
Are all fees included in the Shady holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Shady holiday homes with parking?
Stayz offers a wide selection of holiday homes in Shady with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Shady holiday homes?
You can find great discounts on holiday homes in Shady on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Shady holiday home booking on Stayz?
To find Shady holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Shady?
A long-stay holiday home in Shady is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Shady holiday home?
Book your Shady holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Shady?
Prices for holiday homes in Shady vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Shady to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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