Winchester vacation rentals

We found 232 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
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April 2024
Select from 111 homes, 14 cottages, and other vacation rentals in Winchester to find one that's perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include WiFi and a hot tub. No matter what you're looking for, you'll be able to choose a rental to meet everyone's needs, including accessible or non-smoking choices.

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Travel to charming Winchester

The lake and other outdoor surroundings create an inviting atmosphere in Winchester. Travelers like the theme park, boating and university setting in this romantic and welcoming city. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Winchester

Are you hoping to discover top things to see and do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Winchester a fun spot to vacation. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Tim's Ford Marina (7.9 mi / 12.7 km)
  • Short Springs Natural Area (15.4 mi / 24.8 km)
  • Lynchburg Hardware and General Store (16.4 mi / 26.3 km)
  • Hammers (0.1 mi / 0.1 km)
  • Expressions (0.1 mi / 0.1 km)
  • Sewanee Golf and Tennis Club (11.3 mi / 18.2 km)

Exploring the natural landscape of Winchester

Whether you're an active traveler or just want to take in the scenery, Winchester is a great spot to appreciate mother nature. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Tims Ford State Park (8.5 mi / 13.7 km)
  • Tims Ford Lake (9.4 mi / 15.1 km)
  • Rutledge Falls (16.4 mi / 26.3 km)
  • South Cumberland State Park (18.8 mi / 30.2 km)
  • Great Stage Park (20 mi / 32.3 km)
  • Walls of Jericho Hiking Trailhead (14.6 mi / 23.4 km)

Traveling to and around Winchester

The nearest airport is in Chattanooga Metropolitan Airport (CHA), located 52.8 mi (85 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Huntsville International Airport (HSV), which is 52.8 mi (85 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Winchester?

The most desirable types of vacation rentals in Winchester are houses. Prefer something different? Vrbo has plenty of options to match the unique needs of our guests, so you'll see properties in loads of sizes and shapes. The ideal home away from home is waiting for you — discover yours today.

How much does it cost to rent a vacation rental in Winchester?

Length of stay, season and property type are some factors that can determine the price of a vacation home. Simply enter your travel dates to find the ultimate escape. From cozy chalets to sprawling villas, all Vrbo vacation rentals offer incredible value.

How much does it cost to rent a beach house in Winchester?

The average price for a vacation home by the beach in Winchester depends on when you're going and the size and style of property you want. You can easily and quickly find prices on Vrbo by entering your travel dates. Then use the handy filters to select the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a hot tub.

Are there pet-friendly vacation rentals in Winchester?

Good news. There are. Take your pick of 42 stays that roll out the welcome mat in Winchester on Vrbo. Our furry kids also deserve a little time out, so simply use our search function for pet-friendly vacation rentals to find a perfect property where Rover can lap up the fun.

Can I rent a house with a pool in Winchester?

Mark the "pool" box in our filter tool and you'll find 22 houses with private pools in Winchester on Vrbo. Ball games, gentle soak or noodle joust? How you spend your leisure time is up to you when your Vrbo vacation property comes with its own swimming pool.

What are popular rental amenities in Winchester?

When it comes to rental amenities that guests prefer in Winchester, an electric car charging station, a beach view and nearby museums are the most popular. With Vrbo vacation rentals, you'll enjoy choices to fit your taste and style, whether you're going away with your partner, your friends or even pets.

Are there large group vacation rentals in Winchester?

Take your pick of 12 vacation properties in Winchester that can host a group of 10 or more guests. Whether you're organizing time away with extended family or an event like a birthday party, there's ample room to get your favorite people together under the same roof.

Are there vacation rentals in Winchester that welcome kids?

Winchester has 42 family-friendly vacation rentals to pick from. And securing a stay that welcomes youngsters is super easy with Vrbo's "Properties good for families" filter. As well as having the entire place to yourselves, you'll get access to perks and amenities like bunk beds, full kitchens and yards.

What are the top attractions for families in Winchester?

If you've got the kids in tow, put these family-friendly attractions in Winchester on your list of things to experience:

  • Tims Ford State Park
  • Tims Ford Marina

Are there one-bedroom vacation rentals in Winchester?

Yes, there are four one-bedroom properties in Winchester to pick from. A one-bedroom vacation property is a wonderful choice if it's only the two of you or if you're traveling solo. Toss in more privacy, convenience and space compared to a hotel, and you're bound to have a getaway to remember.

Can I find two-bedroom vacation rentals in Winchester?

Winchester has four two-bedroom properties for you to pick from. Go for a vacation home with all the comfort and privacy you're looking for at a price that won't break the bank on Vrbo.

Are there vacation rentals with WiFi in Winchester?

Whether you'd like to stay in touch with world events, send some emails or update your social media, there are 22 vacation homes with WiFi in Winchester. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.

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