221+ Hotel & Resort Deals in Winchester |
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Winchester Hotels, Resorts, and Rentals

About Winchester Vacation Rentals

There are more than 221 places to stay in Winchester 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 Winchester.

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 Winchester, 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 Winchester. Places to stay near Winchester are 625.95 ft² on average, with prices averaging US $234 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Winchester 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 Winchester

Type Count
Vacation Homes 99
Holiday Apartments 29
Cabin Rentals 8
Cottages 3
Others 3
Unique Vacation Rentals 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Winchester

★ Pro Tip: Hotala 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 Winchester.

Weather in Winchester, IN

View the weather forecast for Winchester before booking your Winchester 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

Stay Near Winchester's Top Attractions

Hotala can help you find hotels, resorts, and rentals near many of Winchester's top attractions, neighborhoods, and points of interest.


Winchester Golf Club
Winchester Speedway
Randolph County Courthouse
Historic Shopping & Dining District of Winchester
Eldora Speedway
Ball State University
Horizon Convention Center
Earlham College
Muncie Civic Theatre
Richmond Art Museum
Richmond Mall
Emens Auditorium
The Winery at Versailles
Richmond Civic Theatre
Darke County Fairgrounds
Glenn Miller Park
Depot District
Prairie Creek Reservoir and Campground
Rose Garden
Warm Glow Candle Company

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Winchester Golf Club 267 Properties
Randolph County Courthouse 263 Properties
Historic Shopping & Dining District of Winchester 263 Properties
Winchester Speedway 31 Properties
White River 26 Properties
Randolph County 24 Properties

Frequently Asked Questions About Winchester?

What are the top hotels or resorts in Winchester?

You have a lot of choices in or near Winchester. If you need a hotel in the Winchester 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 Winchester:

How many vacation rentals have private pools in Winchester?

There are 6 accommodation options with private pools in or near Winchester. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

Which hotel or resort in Winchester is best for families?

If you are looking for a family-friendly hotel, resort, or vacation home in Winchester, check out one of the following places to stay as all are highly-rated accommodation choices with excellent reviews for families or groups staying in Winchester:

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

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 221 in the Winchester area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Winchester.


People Also Ask

There are 74 hotels in Winchester and 137 rentals

Recently Booked Hotels, Resorts, or Rentals in Winchester