102+ Hotel & Resort Deals in Winston |
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Winston Hotels, Resorts, and Rentals

About Winston Vacation Rentals

There are more than 102 places to stay in Winston that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Winston.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Winston, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Winston. Places to stay near Winston are 706.21 ft² on average, with prices averaging CA $215 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Winston with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Winston

Type Count
Vacation Homes 46
Holiday Apartments 17
Cabin Rentals 16
Unique Vacation Rentals 15
Others 4
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Winston

★ Pro Tip: Hotala.ca has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Winston.

Weather in Winston, KY

View the weather forecast for Winston before booking your Winston 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

Frequently Asked Questions About Winston?

What are the top hotels or resorts in Winston?

You have a lot of choices in or near Winston. If you need a hotel in the Winston area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Winston:

How many vacation rentals have private pools in Winston?

There are 2 accommodation options with private pools in or near Winston. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

How many hotels, resorts, or rentals are available in Winston?

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 102 in the Winston area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Winston.


People Also Ask

There are 2 hotels in Winston and 79 rentals

  • Prices for a holiday home in Winston start at CA $89
  • Top rated vacation home in Winston is Oak Tree Inn
  • Most popular short term in Winston is Oak Tree Inn
  • Cheapest place to stay in Winston is Oak Tree Inn
  • Most expensive holiday rental in Winston is Oak Tree Inn

Recently Booked Hotels, Resorts, or Rentals in Winston