Winchester holiday lettings

We found 48 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Winchester to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, which might include cable TV and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Winchester

Showing deals for:7 Nov - 14 Nov

Image gallery for The Ella Norah. A Luxury Retreat. Pool and Spa. Steps to Main Street.

Exterior
10 out of 10 rating
Exceptional
(7 reviews)

The Ella Norah. A Luxury Retreat. Pool and Spa. Steps to Main Street.

Smithville, TX

8% off
Price is £4,486
£641 per night
includes taxes & fees
The Ella Norah. A Luxury Retreat. Pool and Spa. Steps to Main Street.

Find spaces that suit your style

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    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Winchester

Find out more about Winchester

Find the perfect holiday rental for your Winchester getaway

Learn about the unique charm of Winchester with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Winchester

Do you want to find top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Winchester a fun spot to go on holiday. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Bluff Creek Ranch (7.2 mi / 11.5 km)
  • Cotton Bowl Speedway (12.9 mi / 20.7 km)
  • Giddings Country Club (13.1 mi / 21 km)
  • ColoVista Golf Club (15.4 mi / 24.8 km)
  • Frisch Auf Golf Course (11.3 mi / 18.2 km)
  • Jersey Barnyard (11.9 mi / 19.2 km)

Exploring the natural features in Winchester

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Winchester. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Boat Lake (7.8 mi / 12.6 km)
  • Tejas Lake (7.9 mi / 12.7 km)
  • Mid Town Lee Smith Park (13.1 mi / 21.1 km)
  • Goerlitz Lake (15.5 mi / 25 km)

Transport to and around Winchester

The nearest airport is in Austin-Bergstrom International Airport (AUS), located 41.3 mi (66.4 km) from the city centre.

Frequently asked questions

What is the best area to stay in Winchester when booking a holiday rental?
When considering a holiday rental in Winchester, Texas, the area around the historic downtown is a fantastic choice. This charming neighbourhood is not only picturesque but also conveniently located near a number of attractions that highlight the character of Winchester. You can enjoy a leisurely stroll through the streets, where you'll find delightful local shops and eateries, superb for sampling Texan cuisine.

Just a short distance away, the beautiful Lavaca River offers opportunities for outdoor activities such as fishing and kayaking, making it a great spot for those who appreciate nature. The nearby historic sites, such as the local museum, provide fascinating insights into the area's rich history and culture.
How much does it cost to rent a holiday home in Winchester?
Prices for holiday rentals in Winchester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winchester to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winchester holiday house rentals?
You can find great discounts on house rentals in Winchester on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay holiday rentals in Winchester?
A long-stay holiday rental in Winchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Winchester holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winchester with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
How early should I book a Winchester holiday rental?
Book your Winchester holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Winchester home rental booking on Vrbo?
To find Winchester holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winchester holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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