259+ Pet Friendly Hotels and Vacation Rentals in Winchester |
  1. USA
  2. Indiana
  3. Muncie
  4. Winchester

Winchester Pet Friendly Vacation Rentals

About Winchester Vacation Rentals

There are more than 259 places to stay in Winchester and many that are available that welcome pets. These options include dog-friendly 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 pet-friendly places to stay in Winchester.

Are you seeking a last-minute pets-allowed 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 PetFriendly Winchester, you can quickly compare different options to find the hottest deals with a single click. Looking for pet travel at 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 628.23 ft² on average, with prices averaging US $225 a night.

PetFriendly 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 pet-friendly place to stay today.

Show more
Show less

Top Dog Hotels, Pet-Friendly Vacation Rentals, and Places to Stay in Winchester

Type Count
Vacation Homes 119
Holiday Apartments 32
Cottages 3
Villas 2

Use these Quick Filters to Find a Vacation Rental in Winchester

★ Pro Tip: PetFriendly™ has the best results when it comes to finding places to stay that accept pets anywhere around the world. Travelers can find and compare over 10 million listings from all over the world. Use the intelligent Filter feature to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, inns, resorts, and more. Enjoy Pet Travel without Hassle in Winchester.

Weather in Winchester, IN

View the weather forecast for Winchester before booking your hotel or rental.

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, IN

PetFriendly finds and compares Pet-Friendly hotels, rentals, and resort listings near many of Winchester's attractions.


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

Other Places to Stay in Winchester, IN


Winchester Golf Club 246 Properties
White River 244 Properties
Randolph County Courthouse 244 Properties
Historic Shopping & Dining District of Winchester 244 Properties
Winchester Speedway 32 Properties
Randolph County 24 Properties

Frequently Asked Questions About Winchester?

What are the top vacation rentals in Winchester?

Find the best options in or near Winchester for pet-friendly travel. If you are planning a trip or vacation in Winchester, consider a week or two at exciting pets-allowed hotels, resorts, or other suggested properties best known as Top Vacation Rentals and Places to Stay in Winchester:

Which vacation homes in Winchester are best for families?

Are you looking for a family-friendly and pet-friendly hotel, resort, or vacation home in Winchester? Check these highly-rated pet accommodations and places to stay with excellent reviews for families or groups staying in Winchester:

How many PetFriendly vacation rentals are available in Winchester?

PetFriendly™ updates its properties regularly to bring you a great selection of places to stay with their pet policies clearly spelled out. At present, the total number of active properties listed by PetFriendly in 2026 is over 259 in the Winchester area, and still growing every day. When we combine listings from multiple websites and travel providers, PetFriendly can provide you with a huge selection of the best places to stay that welcome pets in Winchester.


People Also Ask

There are 259 Winchester, IN Vacation Rentals

Recently Booked Pet Friendly Hotels and Vacation Rentals in Winchester