Shady holiday homes

We found 587 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:13 Nov - 20 Nov

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

Secluded Cabin with Hot Tub - 5 Miles to Woodstock

Bearsville

8% off
NZ$5,069
for 7 nights, 1 cabin
NZ$724 per night
includes taxes & fees
Secluded Cabin with Hot Tub - 5 Miles to Woodstock
Private kitchen
Living area
Private kitchen
Pool
Wonderful
(23 reviews)

Large 11 Bedroom 5 bathrooms minutes to Hunter & walk to Tannerville

Tannersville

12% off
NZ$8,307
for 7 nights, 1 home
NZ$1,187 per night
includes taxes & fees
Large 11 Bedroom 5 bathrooms minutes to Hunter & walk to Tannerville
Living area
Interior
Private kitchen
Living area
Exceptional
(134 reviews)

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville

11% off
NZ$10,321
for 7 nights, 1 home
NZ$1,474 per night
includes taxes & fees
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Living area
Exterior
Private kitchen
Pool
Exceptional
(49 reviews)

Secluded family retreat within minutes of Woodstock village

Saugerties

8% off
NZ$5,648
for 7 nights, 1 home
NZ$807 per night
includes taxes & fees
Secluded family retreat within minutes of Woodstock village
Interior
Your primary entrance will lead you directly in the homes cool kitchen!
 Kitchen comes fully stocked with pots/pans, dishes, silverware, glasses, etc.
Exterior
Exceptional
(88 reviews)

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

Haines Falls

8% off
NZ$11,355
for 7 nights, 1 home
NZ$1,622 per night
includes taxes & fees
Featured on MTV ! You Have To See It To Believe It ! Unlike any other !
Exterior
Living area
Exterior
Dining
Exceptional
(39 reviews)

5-Star New Barn Home - Music Studio, Views & Hot Tub

Saugerties

8% off
NZ$10,128
for 7 nights, 1 home
NZ$1,447 per night
includes taxes & fees
5-Star New Barn Home - Music Studio, Views & Hot Tub
Living area
Room
Private kitchen
Outdoor dining
Exceptional
(6 reviews)

Cozy and bright 2-bedroom cabin in charming Elka Park

Tannersville

8% off
NZ$2,481
for 7 nights, 1 cabin
NZ$354 per night
includes taxes & fees
Cozy and bright 2-bedroom cabin in charming Elka Park
Wall-to-wall closets and beautiful wood beam ceiling
Living room with wonderful light and mountain views (winter) and woods (summer)
Property grounds
High ceilings and TV with Netflix, Amazon and more
Exceptional
(36 reviews)

Modernized A-Frame Chalet in the Heart of the Hudson Valley

Saugerties

8% off
NZ$5,004
for 7 nights, 1 home
NZ$715 per night
includes taxes & fees
Modernized A-Frame Chalet in the Heart of the Hudson Valley
Great room featuring a wonderful wall of windows
Private kitchen
Kitchen with everything you'll need
Exterior
Exceptional
(52 reviews)

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

Woodstock

12% off
NZ$6,046
for 7 nights, 1 home
NZ$864 per night
includes taxes & fees
Private Woodstock Retreat – Heated Pool, Hot Tub & Fireplace on 5 Secluded 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!!
new, beautiful, fully equipped, large, custom kitchen-plenty of counter space.
Exceptional
(163 reviews)

Sanctuary by the Stream

Phoenicia

13% off
NZ$3,478
for 7 nights, 1 home
NZ$497 per night
includes taxes & fees
Sanctuary by the Stream
Room
Dining room table with bay window.
Private kitchen
The den is wide open with an oversized couch, coffee tables and stool seating.
Exceptional
(39 reviews)

Spacious, Private, Close to Town, Work From Home

Woodstock

7% off
NZ$5,417
for 7 nights, 1 home
NZ$774 per night
includes taxes & fees
Spacious, Private, Close to Town, Work From Home
Living area
Property grounds
Living area
Private kitchen
Exceptional
(13 reviews)

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

Mount Tremper

12% off
NZ$10,724
for 7 nights, 1 home
NZ$1,532 per night
includes taxes & fees
"Frank Lloyd Wright" Catskills Mountain Yoga-Spa Retreat on 15 Acres
Fern garden in summer
Welcome to Bridge House
Large sliders bring nature indoors
In winter, stay toasty warm by the fire
Exceptional
(128 reviews)

Waterfront Mid-century Modern Gem Surround by Forever Wild Land

Willow

8% off
NZ$4,236
for 7 nights, 1 home
NZ$605 per night
includes taxes & fees
Waterfront Mid-century Modern Gem Surround by Forever Wild Land
Property grounds
Property grounds
Room
Interior
Exceptional
(17 reviews)

Hudson Valley’s Private Waterfront Camping Getaway

Lake Katrine

8% off
NZ$2,760
for 7 nights, 1 unit
NZ$394 per night
includes taxes & fees
Hudson Valley’s Private Waterfront Camping Getaway
Entrance to Tannery Brook Cottage in July with Front Porch and Day Lilies
Terraced Rock Garden with Rustic Stone Walls and Massive Steps
Dining Area with Curio Cabinet, Book Shelf and Office Nook with Computer Station
Open Plan Kitchen / Dining Area with French Doors and Screen Porch in Distance
Exceptional
(18 reviews)

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

Woodstock

11% off
NZ$4,317
for 7 nights, 1 cottage
NZ$617 per night
includes taxes & fees
Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.
Living area
Exterior
Dining
Private kitchen
Exceptional
(10 reviews)

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

Lake Hill

8% off
NZ$3,621
for 7 nights, 1 cabin
NZ$517 per night
includes taxes & fees
Most Charming, Most quiet place in the Catskills--Willow-brook Cottage
11 ft dining table seats 10-14 people
Covered 15' picnic table for enjoying meals al fresco.
Pool is open Memorial Day through Labor Day.
Sun room - Sofa converts to full-size bed & doors close to make a cozy bedroom.
Exceptional
(7 reviews)

Experience the Catskills - Explore, Entertain and Relax at our Chalet.

Lanesville

16% off
NZ$5,020
for 7 nights, 1 home
NZ$717 per night
includes taxes & fees
Experience the Catskills - Explore, Entertain and Relax at our Chalet.
Living area
Dining
Private kitchen
Interior
Exceptional
(26 reviews)

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

Glenford

5% off
NZ$5,954
for 7 nights, 1 home
NZ$851 per night
includes taxes & fees
Gorgeous Villa w/ Mountain Views, pool, hot tub!
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
NZ$4,908
for 7 nights, 1 apartment
NZ$701 per night
includes taxes & fees
Hunter Mountains Hill Top Hide Away Trail Side
Interior
Living area
Dining Room Looking out to Private Lake
Interior
Exceptional
(26 reviews)

Incredible Lake House with Stunning Mountain Views (swimming lake)

Chichester

7% off
NZ$5,865
for 7 nights, 1 home
NZ$838 per night
includes taxes & fees
Incredible Lake House with Stunning Mountain Views (swimming lake)
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.
Eat-in country kitchen with all appliances, including dishwasher and microwave.
Exceptional
(46 reviews)

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

Phoenicia

8% off
NZ$4,115
for 7 nights, 1 home
NZ$588 per night
includes taxes & fees
Beautiful large Woodland Valley/Phoenicia post & beam cabin with seasonal stream
Interior
Property grounds
Private kitchen
Dining
Exceptional
(89 reviews)

Private Woodstock / Saugerties 2BR w/ Hot Tub, Fireplace and Pet Friendly

Saugerties

8% off
NZ$3,795
for 7 nights, 1 home
NZ$542 per night
includes taxes & fees
Private Woodstock / Saugerties 2BR w/ Hot Tub, Fireplace and Pet Friendly
Dining
Terrace/patio
Private kitchen
Exterior
Exceptional
(28 reviews)

Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!

Hurley

12% off
NZ$3,155
for 7 nights, 1 cabin
NZ$451 per night
includes taxes & fees
Cabin 85: 2 Bedrooms + 2 Lofts Perfect Retreat!
Exterior
Exterior
Living area
Dining
Exceptional
(6 reviews)

Charming 3-bedroom bungalow with AC in Phoenicia, Catskills

Phoenicia

8% off
NZ$4,716
for 7 nights, 1 home
NZ$674 per night
includes taxes & fees
Charming 3-bedroom bungalow with AC in Phoenicia, Catskills
  • 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:

  • Hunter Mountain (9.8 mi / 15.8 km)
  • Kaaterskill Falls (9.9 mi / 16 km)
  • Windham Mountain Resort (16.2 mi / 26 km)
  • Indian Head Mountain (5.4 mi / 8.7 km)
  • Mountain Trails Cross Country Ski and Snowshoe Center (8.8 mi / 14.2 km)
  • Saugerties Town Hall (10.3 mi / 16.6 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

What is the most popular type of holiday home accommodation in Shady?
The most sought-after types of holiday homes in Shady are chalets. After something a little different? Bookabach has many options to match the unique needs of our guests, so you'll see holiday homes in loads of sizes and shapes. The perfect fit is waiting for you — snap up yours today.
How much does it cost to rent a holiday home in Shady?
The average price for a holiday home in Shady can vary depending on factors like length of stay, property type and season. Whether you're in search of a villa with space for extended family or a cosy condo just for the two of you, just enter your dates of travel to find stays with exceptional value.
How much does it cost to rent a beach house in Shady?
Prices for beach houses in Shady can differ depending on the type and size of the property and time of year you're travelling. All you need to do is enter your travel dates into Bookabach and how many guests to view holiday home options and prices. From there you can use the filters to narrow your search results by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday homes in Shady?
With two properties that welcome four-legged guests, your furry buddy can join you on your Shady break. Use our filter tool to browse our pet-friendly holiday homes and find a holiday home that'll set tails wagging on Bookabach.
What are popular home amenities in Shady?
When it comes to home amenities that guests are looking for in Shady, a fireplace, mountain views and a firepit rank highest. With Bookabach holiday homes, there are options to fit your style and taste, whether you're planning to get away with family members, friends or even pets.
Are there holiday homes in Shady that welcome kids?
Bring the entire family together for an unforgettable adventure in Shady at one of our two family-friendly holiday homes. These stays offer amenities that are ideally suited to trips with children, such as laundries, bunk beds and patios. Simply click on the "Properties good for families" filter box and book your favourite.
What are the top attractions for families in Shady?
You'll find loads of cool things to see and do with the family in Shady, including:
  • Overlook Mountain Trailhead
  • SweetHeart Gallery
  • Karma Triyana Dharmachakra Monastery
How can I find holiday homes with air conditioning in Shady?
Pick from two Bookabach holiday homes with air conditioning in Shady giving you that gentle, cool breeze and extra bit of comfort. Simply enter your chosen travel dates and then use our handy filters to locate properties with air conditioning.
How old do you have to be to rent a holiday home in Shady?
We recommend you check with the Shady holiday home you're considering on Bookabach as age restrictions vary. However, it's normally 16, 18 or 21.
How long can I rent a holiday home in Shady for?
The length of time you can rent a holiday home in Shady depends on the property. Simply enter your selected dates to see a list of options offering extended stays. With plenty of amenities like washing machines and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to find the perfect place to call your home away from home in Shady.