Pirate Cove Cottages - Vacation Rentals in Shady

Romantic, Magical Cottage in Catskills nr Woodstock From US $379
         

Private Woodstock Retreat In Town Hot Tub Dog Friendly From US $361
         

9.8 (140 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Shady

Over 163+ Luxury Places to Stay in or Near Shady
Walk To Woodstock, Streamside W/In Ground Pool From US $2,544
         

10.0 (40 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Woodstock Historic Artist Estate - The Museum House From US $1,182
         

9.8 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Shady

Over 31+ Top-Rated Vacation Rentals with a Pool in or Near Shady
HOT TUB w/POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN From US $732
         

10.0 (107 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Mid-Century Modern Gem, Heated Pool, 1 Mile from Town From US $777
         

10.0 (35 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern Farmhouse Getaway From US $819
         

10.0 (25 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Twin Gables of Woodstock From US $202
         

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9.8 (210 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Shady

Over 57+ Pet-Friendly Vacation Rentals in or Near Shady
Romantic Cottage -Amazing Views -Spa -Woodstock NY From US $326
         

10.0 (83 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Fiber Artist's Studio From US $180
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Pet Friendly Cabin Doh-Ray up @ 1500 ft From US $358
         

10.0 (67 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Woodstock House on 35 private acres Mountain Views From US $532
         

10.0 (55 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Woodstock historic artist estate - The Pond House From US $722
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Shady on PetFriendly.io

Large Vacation Homes & Villas in Shady

Over 6+ Large Vacation Homes & Villas in or Near Shady
Secluded Cabin with Hot Tub - 5 Miles to Woodstock From US $394
         

Morning Glory B n B Woodstock NY From US $199
         

8.5 (63 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View
🇺🇦Byrdcliffe Arts Colony in the Catskills w/Hot Tub From US $841
         

STREAMSIDE Walk To Town, Hot Tub, 4 Br 2.5 Bath, Game Room From US $200
         

5.0 (11 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Shady

Over 2+ Wheelchair Accessible Vacation Homes in or Near Shady
The Herwood Inn From US $416
         

9.4 (71 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Woodstock Way Hotel From US $245
         

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9.2 (184 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Shady Vacation Rentals and Airbnb Places to Stay Under $200

Over 32+ Shady Vacation Rentals and Airbnb Places to Stay Under $200
Quiet 2-bedroom cottage in peaceful Lake Hill From US $199
         

New
Cottage
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Mid-Century Woodstock Retreat From US $172
         

Tentrr Signature Site - Shady Knolls From US $161
         

5.0 (4 Reviews)
RV Rental
  • Pet Friendly
  • Balcony/Terrace
  • Child Friendly
Cottage - Wildflower Suite From US $112
         

10.0 (29 Reviews)
Apartment
  • Pet Friendly
  • Security/Safety
  • Guest Services

Instantly Bookable Vacation Homes in Shady

Over 54+ Instantly Bookable Vacation Homes in or Near Shady
Maple House: Private/Romantic Walk-to-Town Oasis From US $476
         

Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi From US $273
         

Renovated home seconds from town From US $347
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Adorable Red Cottage, walking distance to Woodstock From US $243
         

10.0 (1 Review)
Cabin
  • Air Conditioner
  • Pet Friendly
  • TV
COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK! From US $607
         

9.8 (78 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

About Shady Vacation Rentals

With more than 25 Shady vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Piratecovecottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Shady.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Piratecovecottages Shady, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Shady. Places to stay near Shady are 427.92 ft² on average, with prices averaging US $303 a night.

Piratecovecottages makes it easy and safe to find and compare vacation rentals in Shady with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Shady

Type Count
Cottages 24
Vacation Homes 1

Use these Quick Filters to Find a Vacation Rental in Shady

Pro Tip: Piratecovecottages makes it easy to compare the best listings on Piratecovecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Piratecovecottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Shady.

Weather in Shady

View the weather forecast for Shady before booking your Shady Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Shady Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Shady?
How many vacation rentals are available in Shady?

Currently, the total number of properties listed in 2026 is over 25 in the Shady area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Shady.