Winchester holiday rentals

We found 252 holiday rentals — enter your dates for availability

your current months are October, 2024 and November, 2024.
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Select from 121 homes, 14 cottages and other holiday rentals in Winchester to find one that's perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you expect for your stay, which might include parking and a pool. Whatever you're looking for, you'll be sure to find a property to rent for 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. Travellers especially like the theme park, boating and university setting in this romantic and welcoming city. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Winchester

Do you want to discover attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Winchester a fun spot to go on holiday. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Tim's Ford Marina (7.9 mi / 12.7 km)
  • Sewanee Golf and Tennis Club (11.3 mi / 18.2 km)
  • Short Springs Natural Area (15.4 mi / 24.8 km)
  • May Prairie Natural Area (20.4 mi / 32.8 km)
  • Hammers (0.1 mi / 0.1 km)
  • Expressions (0.1 mi / 0.1 km)

Exploring the natural landscape of Winchester

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Winchester is a great place to spend some time outside. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Tims Ford State Park (8.5 mi / 13.7 km)
  • Tims Ford (9.2 mi / 14.8 km)
  • Tims Ford Lake (9.4 mi / 15.1 km)
  • Lake Cheston (10.4 mi / 16.8 km)
  • Walls of Jericho Hiking Trailhead (14.6 mi / 23.4 km)
  • Rutledge Falls (16.4 mi / 26.3 km)

Travelling to and around Winchester

The nearest airport is in Chattanooga, TN (CHA-Chattanooga Metropolitan), located 52.8 mi (85 km) from the city centre. If you can't find a flight that's convenient for your trip, 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 holiday home accommodation in Winchester?

The most desirable types of holiday homes 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 holiday home in Winchester?

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

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

The average price for a holiday 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 holiday homes 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 holiday homes 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 holiday property comes with its own swimming pool.

What are popular home amenities in Winchester?

When it comes to home amenities that guests prefer in Winchester, an electric car charging station, a beach view and nearby museums are the most popular. With Vrbo holiday homes, 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 holiday homes in Winchester?

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

Are there holiday homes in Winchester that welcome kids?

Winchester has 42 family-friendly holiday homes 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 holiday homes in Winchester?

Yes, there are four one-bedroom properties in Winchester to pick from. A one-bedroom holiday property is a wonderful choice if it's only the two of you or if you're travelling 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 holiday homes in Winchester?

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

Are there holiday homes 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 holiday homes with WiFi in Winchester. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.

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