Best Vacation Homes in Winston
House
10.0(165 Reviews)
6 Bedrooms
3 Baths
14 Guests
4200 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Kitchen
AU $636/Night
7 Nights - AU $4,452
House
10.0(2 Reviews)
1 Bedroom
2 Baths
5 Guests
1194.79 ft²
Parking
Air Conditioner
Internet
Child Friendly
AU $215/Night
7 Nights - AU $1,506
AU $91/Night
7 Nights - AU $640
Cabin
10.0(104 Reviews)
1 Bedroom
1 Bath
3 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Internet
AU $182/Night
7 Nights - AU $1,277
House
10.0(1 Review)
3 Bedrooms
3 Baths
8 Guests
2604.87 ft²
- Fireplace/Heating
- Balcony/Terrace
View
Pet Friendly
AU $418/Night
7 Nights - AU $2,928
Cabin
10.0(72 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $234/Night
7 Nights - AU $1,636
Apartment
10.0(50 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $184/Night
7 Nights - AU $1,288
House
10.0(47 Reviews)
3 Bedrooms
2 Baths
8 Guests
1100 ft²
- Hot Tub
- Fireplace/Heating
Ocean View- Balcony/Terrace
AU $307/Night
7 Nights - AU $2,149
Winston Luxury Rentals
House
6 Bedrooms
6 Baths
30 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $1,782/Night
7 Nights - AU $12,477
House
5 Bedrooms
3 Baths
15 Guests
3498.27 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
AU $818/Night
7 Nights - AU $5,725
House
5 Bedrooms
3 Baths
15 Guests
3500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $577/Night
7 Nights - AU $4,039
Cabin
9.6(25 Reviews)
5 Bedrooms
3 Baths
15 Guests
4500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $490/Night
7 Nights - AU $3,432
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
7 Guests
3446 ft²
- Hot Tub
Spa- Fireplace/Heating
- Ocean View
AU $488/Night
7 Nights - AU $3,415
House
8.5(2 Reviews)
3 Bedrooms
2 Baths
7 Guests
3595.15 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Parking
AU $478/Night
7 Nights - AU $3,349
Bed & Breakfast
10.0(1 Review)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $468/Night
7 Nights - AU $3,277
Other
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $457/Night
7 Nights - AU $3,202
Winston Pet Friendly Vacation Rentals
Cabin
10.0(19 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $305/Night
7 Nights - AU $2,136
House
9.8(6 Reviews)
1 Bedroom
1 Bath
5 Guests
247.57 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
AU $214/Night
7 Nights - AU $1,497
Cabin
10.0(17 Reviews)
1 Bedroom
1 Bath
4 Guests
248 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $185/Night
7 Nights - AU $1,296
AU $104/Night
7 Nights - AU $726
Apartment
10.0(16 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $238/Night
7 Nights - AU $1,669
Apartment
10.0(11 Reviews)
3 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
AU $192/Night
7 Nights - AU $1,346
Cabin
10.0(10 Reviews)
2 Bedrooms
1 Bath
6 Guests
818 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $228/Night
7 Nights - AU $1,598
Apartment
10.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $197/Night
7 Nights - AU $1,376
Winston Large Vacation Homes
New
Bed & Breakfast
3 Bedrooms
1 Bath
17 Guests
- Fireplace/Heating
- Air Conditioner
- Child Friendly
Laundry
AU $306/Night
7 Nights - AU $2,145
House
10.0(69 Reviews)
4 Bedrooms
2 Baths
10 Guests
2558 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $491/Night
7 Nights - AU $3,434
Cabin
4.9(39 Reviews)
3 Bedrooms
2 Baths
10 Guests
Private Pool
Pool- Pet Friendly
- Kitchen
AU $360/Night
7 Nights - AU $2,517
Cabin
5 Bedrooms
3 Baths
4500 ft²
- Child Friendly
AU $462/Night
7 Nights - AU $3,234
Why Choose Rent By Owner for your Winston Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Winston
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit here ensures you experience the region's best weather and activities, making your stay in Winston, Kentucky, USA, truly memorable.
Peak Season Highlights
Spring (March to May)
During spring, you can enjoy the region's vibrant natural beauty and pleasant weather, making it an ideal time for outdoor activities and exploring local scenery.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Fall (September to November)
Autumn offers cooler temperatures and stunning foliage, perfect for sightseeing and experiencing the area's scenic landscapes at their most colorful.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Summer (June to August)
In summer, the region experiences warmer weather, providing opportunities for outdoor recreation and enjoying the longer daylight hours in this destination.
Average Temperature Daytime: 80°F to 90°F - Nighttime: 60°F to 70°F
Winter (December to February)
Winter brings colder temperatures, but it's a quieter period for visitors seeking peaceful stays and cozy accommodations in the area.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
Weekly Weather Forecast for Winston
How to Book Your Winston Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Winston
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor pool to relax and unwind during your stay.
- Take advantage of scenic patios or decks for outdoor dining and entertaining.
- Explore spacious gardens or yards perfect for outdoor activities or pets.
- Make use of outdoor grills or barbecue facilities for delicious al fresco meals.
- Benefit from well-maintained walking paths or hiking trails nearby for outdoor adventures.
- Relax in a hot tub or spa area, ideal for unwinding after a day of exploring the region.
- Experience the beauty of outdoor fireplaces or fire pits, perfect for gathering with friends or family.
Top Attractions Around Winston
What attractions are nearby?
Nearby, you can explore a variety of outdoor activities and local attractions that showcase the best of this destination, making it an ideal spot for memorable experiences during your stay.
Family Activities
- Winston Family Fun Center: Enjoy a day of arcade games, mini-golf, and attractions designed to entertain kids and adults alike in the area.
- Local Nature Trails: Explore scenic hiking and biking trails that provide outdoor adventures suitable for all ages here in this welcoming destination.
- Community Park & Playground: Relax and play at the park featuring spacious playgrounds, picnic areas, and open fields perfect for family gatherings in the region.
- Historical Museum Visit: Discover the area's rich history and culture through engaging exhibits that are educational and fun for family members of all ages.
Adult Activities
- Wine Tasting Tours: Explore the local wineries in the area to enjoy tasting regional wines and learning about the region’s viticulture.
- Golfing at Premier Courses: Spend your day on well-maintained golf courses that showcase the scenic landscapes of this destination, perfect for golf enthusiasts.
- Hiking and Nature Walks: Discover the region's natural beauty through numerous trails, offering peaceful surroundings and picturesque views.
- Historic Downtown Exploration: Stroll through the charming downtown area featuring unique shops, galleries, and inviting cafes that highlight the area's heritage.
Winston Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take the time to discover hidden gems and scenic spots around Winston that showcase the region's natural beauty and local culture.
- Plan Your Transportation: Arrange convenient transportation options ahead of time to make the most of your stay and easily access all the best sites in this destination.
- Book Well in Advance: Secure your preferred vacation rentals early to ensure a comfortable stay during peak seasons and avoid last-minute availability issues.
- Embrace the Local Cuisine: Make sure to try regional dishes and dine at local eateries to immerse yourself in the authentic flavors of the area.
Transportation Options
- Winston City Bus Service: The local bus service offers convenient transportation around the area, making it easy for you to explore your surroundings without needing a car.
- Rental Cars: Several rental agencies operate here, providing flexible options for exploring the region at your own pace and visiting nearby attractions.
- Taxis and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available, offering quick and reliable transportation throughout the destination.
- Bicycle Rentals: For a more eco-friendly experience, bicycle rentals are offered around here, allowing you to enjoy scenic routes and outdoor activities during your stay.
Local Customs Options
- Southern Hospitality: You will notice the warm and welcoming attitude of locals, reflecting the region's rich tradition of southern hospitality in Winston, Kentucky.
Engaging with local folk music during events offers a glimpse into the area's cultural heritage, making it a memorable part of your stay here. - Cultural Festivals: Participating in community festivals allows you to experience the lively customs and celebrations unique to this destination.
- Local Cuisine Etiquette: When dining in the region, you'll find that sharing meals and engaging in friendly conversation are important aspects of local custom, enhancing your visit to Winston, Kentucky.
Frequently Asked Questions About Winston?
1. What are the top vacation rentals in Winston?
There are a lot of options in Winston. If you plan on staying in the Winston area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winston:
- Authentic, Rustic, Historic Log Cabin
- Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
- Spacious Secluded Cabin on 100 Acres Near Red River Gorge
- Luxury on Main/South
- Hot Tub! Fire pit! Picnic area & Grill! View Hardwicks Creek Haven@RRG
- Comfy Upstairs 2 bed/1 bath near EKU in Richmond
- Cozy upstairs 2 bed/1 bath Richmond apt near EKU
- Stargazer Cabin-Look Up. Relax. Repeat.
- New Downtown Irvine 3/2 home w/king bed. Near Red River Gorge, Berea, Lex.
- 540-acre farm with trails, creeks, animals & nearby attractions
2. Which vacation homes in Winston are best for families?
If you are looking for a family-friendly vacation home in Winston, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winston:
3. How many Rentbyowner vacation rentals are available in Winston?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 116 in the Winston area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winston.
4. What is the cancellation policy for vacation rentals in Winston, Kentucky?
Cancellation policies can vary depending on the host and specific listing. It is recommended to review the cancellation terms listed with your chosen property or contact the owner directly for detailed information.
5. Are there any house rules I should be aware of when booking a vacation rental in Winston?
Yes, each property has its own set of house rules which are outlined in the listing. Be sure to read these carefully before booking to ensure a smooth stay.
6. How do I find the best vacation rental deals in Winston, Kentucky?
You can browse available listings and filter your search based on amenities, price range, and reviews. Reading guest reviews and host responses will also help you find a property that fits your needs.
7. Is there a minimum stay requirement for vacation rentals here?
Minimum stay requirements vary by property. Details are specified in each listing, so it’s advisable to check this information before completing your reservation.
8. What should I do if I need to cancel my booking in Winston?
If you need to cancel, review the property's cancellation policy and follow the procedure outlined in your booking confirmation. For assistance, you can contact the host directly through the platform.
Winston Top Rated Vacation Rentals
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
AU $218/Night
7 Nights - AU $1,526
Other
9.8(28 Reviews)
3 Bedrooms
1 Bath
4 Guests
1700 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
AU $53/Night
7 Nights - AU $372
House
8.8(18 Reviews)
3 Bedrooms
1 Bath
6 Guests
1755 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $353/Night
7 Nights - AU $2,474
House
1 Bedroom
1 Bath
6 Guests
161.46 ft²
- Fireplace/Heating
- Pool
- View
- Air Conditioner
AU $424/Night
7 Nights - AU $2,970
Other
10.0(18 Reviews)
4 Bedrooms
2 Baths
8 Guests
2200 ft²
- Private Pool
- Pool
- Kitchen
- Air Conditioner
AU $178/Night
7 Nights - AU $1,249
