The Islands Advisors - Vacation Rentals in Wildside Winery

Orchard Park cottage From US $706
         

10.0 (132 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Charred Oaks Inn From US $359
         

|
9.7 (13 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
High style on the Bourbon Trail From US $180
         

10.0 (111 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Montgomery Inn BnB From US $229
         

|
7.8 (24 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
History & Hospitality at the Woodford Inn From US $283
         

Rose Hill Inn From US $261
         

9.9 (67 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Charred Oaks Inn From US $517
         

|
10.0 (38 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Man o’ War Cottage | Versailles KY Stay From US $267
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Secretariat Cottage | Cozy Versailles Getaway From US $263
         

Justify Cottage – Near Keeneland & Distilleries From US $556
         

Zenyatta Cottage | 3BR Retreat in Horse Country From US $509
         

Woodford Stables/Walk to Eckert's Orchard From US $360
         

9.6 (24 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bourbon Trail! Prime Location, Amenities & Sauna! From US $407
         

Historic Downtown Morgan Street Apartment - Pet Friendly! From US $141
         

9.4 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Heritage Lodge - New! From US $2,878
         

8.8 (6 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
3 MILES from KEENELAND! Located right off Versailles road From US $469
         

Pro Tip: Theislandsadvisors makes it easy to compare the best listings on Theislandsadvisors homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Theislandsadvisors 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 Wildside Winery.

Weather in Wildside Winery

View the weather forecast for Wildside Winery before booking your Wildside Winery 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

Wildside Winery Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Wildside Winery?
How many vacation rentals are available in Wildside Winery?

Currently, the total number of properties listed in 2026 is over 74 in the Wildside Winery area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Wildside Winery.