Winchester holiday lettings

We found 252 holiday rentals — enter your dates for availability

Select from 114 homes, 13 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.

Holiday rentals with weekly discounts - Winchester

Showing deals for:3 Oct - 10 Oct
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Why visit Winchester

  • Outdoor adventures: Enjoy stunning scenery with ample opportunities for hiking, boating, and exploring local parks.
  • Historic sites: Visit significant landmarks like Winchester Cathedral and Winchester Castle for a glimpse into the city's rich history.
  • Family-friendly attractions: Explore the local marina and marine park, perfect for a delightful family day out.
  • Charming accommodation: Choose from lovely private homes, cosy cabins, and inviting cottages for a comfortable stay.
  • Romantic getaways: Experience the charm and beauty of Winchester, ideal for couples seeking a romantic escape.

Popular types of accommodation in Winchester

If you’re seeking the perfect getaway in Winchester, look no further! Our platform offers a delightful selection of accommodation options, including charming houses, cosy cabins, and inviting cottages. Whether you’re searching for Winchester holiday rentals, holiday cottages, or general accommodation in Winchester, we’ve got the ideal stay for you. Enjoy transparency, savings, and reassurance as you explore the beauty of this historic city.

  • Houses: The top choice for visitors seeking a home-away-from-home experience in Winchester, ideal for families or groups.
  • Cabins: A charming option for those looking to immerse themselves in nature, offering rustic comfort and scenic surroundings.
  • Cottages: Quaint and cosy, these properties provide a delightful retreat for couples or small families.
  • Apartments: Conveniently located, these self-contained lodgings are perfect for those wanting easy access to local amenities.
  • Chalets: A unique option that combines comfort and style, often set in picturesque locations.**

Top attractions in and around Winchester

Winchester, Tennessee, is perfect for outdoor and romantic getaways, offering stunning scenery and a variety of attractions. Visitors can explore the local marina, marine park, and beautiful islands, providing a delightful family experience. Don’t miss the opportunity to visit historic sites like Winchester Cathedral, take a tour of Winchester, and discover Winchester Castle, all while enjoying the charm of this lovely city.

  • Tim's Ford Marina: Nestled in Winchester, Tim's Ford Marina offers a delightful blend of adventure and relaxation. Enjoy beach vibes and outdoor activities such as boating, fishing, and picnicking, making it a perfect spot for families and friends to unwind amidst nature.
  • Expressions: A charming attraction in Winchester, Expressions exudes romantic vibes, ideal for couples. It’s a lovely place to enjoy art, craft, and local culture, making it perfect for a memorable date or a thoughtful gift.
  • Elk River Dam: Located 5.0km from Winchester, Elk River Dam provides stunning views and outdoor adventures. It’s a romantic spot for couples, offering hiking trails and scenic overlooks, perfect for a day of exploration and connection with nature.

Things to do recommended for couples

Winchester offers charming experiences for couples, such as a leisurely walk around the picturesque Tims Ford Lake, a wine tasting at a local vineyard, or a romantic picnic in the serene Old City Cemetery. Don’t miss the delightful boutiques and cosy cafes in the town centre.

Things to do recommended for families

Families visiting Winchester, Tennessee, can enjoy the outdoor vibes at Hank Weddington Park, just 1.2km away. For relaxation, head to the City of Decherd Babe Ruth Ball Park, 1.9km out, or the Pleasant Grove Public Use Area, located 4.3km from Winchester.

Things to do recommended for groups

Experience the rich heritage of whiskey at the Jack Daniel's Distillery, just 9.9km from Winchester. Enjoy shopping at Hammers in town, or indulge in outdoor activities at the Sewanee Golf and Tennis Club, located 6.8km away, perfect for sports enthusiasts.

Booking with Vrbo is simple

Are you hoping to cut costs on your next holiday? It’s worth considering some flexibility with your travel dates, as prices can vary quite a bit. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of accommodation.

Where to stay near Winchester

Winchester, Tennessee, is a charming destination perfect for outdoor enthusiasts and couples alike. With a friendly atmosphere and picturesque scenery, you'll find delightful spots for family-friendly fun and romantic moments. Explore nearby towns for a taste of culture and recreation, and immerse yourself in the local vibe. Whether you're enjoying the beautiful landscapes or engaging in urban experiences, Winchester offers a delightful escape filled with entertainment and memorable adventures.

  • Sewanee: Sewanee is a picturesque city located 6.8km from Winchester, known for its breathtaking outdoor scenery and romantic atmosphere. The area is home to the historic Sewanee: The University of the South, which is renowned for its stunning Gothic architecture and rich history. Visitors can enjoy a variety of recreational activities, including hiking trails that lead to the stunning natural beauty of nearby state parks and lakes. The combination of educational opportunities and outdoor adventures makes Sewanee a delightful stop for those seeking both culture and nature.
  • Tullahoma: Situated 8.1km from Winchester, Tullahoma offers a charming blend of outdoor exploration and scenic landscapes, making it an ideal destination for romantics and nature enthusiasts alike. The city features several recreational areas and campgrounds, perfect for a leisurely day out or a weekend getaway. Nearby attractions include serene lakes and national state parks, as well as a fascinating local museum showcasing the region's heritage. Tullahoma’s welcoming atmosphere and array of outdoor activities promise an enjoyable experience for all visitors.
  • Decherd: Located a mere 1.2km from Winchester, Decherd is a vibrant city that invites guests to explore its scenic beauty and outdoor offerings. Known for its recreational areas and campgrounds, Decherd is perfect for those who enjoy nature walks and tranquil lakeside experiences. The city is also in proximity to a historic college university and national state park, providing ample opportunities for education and adventure. With its charming environment and romantic allure, Decherd is a fantastic spot for a peaceful retreat.

Best time to go to Winchester

If you're planning a trip to Winchester, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January38.3°F (3.5°C)Light RainMostly CloudyAverageSlightly Low
February42.8°F (6.0°C)Light RainMostly CloudyAverageSlightly Low
March50.4°F (10.2°C)Light RainMostly SunnyAverageSlightly Low
April57.9°F (14.4°C)Light RainMostly SunnySlightly HighAverage
May66.7°F (19.3°C)Light RainMostly SunnyAverageAverage
June74.5°F (23.6°C)Light RainMostly SunnySlightly HighSlightly High
July76.8°F (24.9°C)Light RainMostly SunnySlightly HighSlightly High
August75.6°F (24.2°C)Light RainMostly SunnyAverageSlightly High
September70.5°F (21.4°C)Light RainMostly SunnyAverageAverage
October59.9°F (15.5°C)Light RainMostly SunnySlightly LowAverage
November48.9°F (9.4°C)Light RainMostly SunnySlightly LowAverage
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

What do I need to keep in mind when booking a vacation in 'Winchester

If you're travelling with a group, family, or pets, or if you're considering longer stays, be sure to apply the appropriate filters to match your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winchester with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor space for group activities. Thankfully, you can easily apply these filters and more on Vrbo.
  • Traveling to Winchester with young kids: Embarking on a journey with young children can present its difficulties. It's essential to prioritise their comfort and safety, along with suitable amenities for their age, such as a private swimming pool. Additionally, it's wise to take into account your closeness to attractions that are family-friendly.
  • Taking your pets with you to Winchester: For many, a family holiday wouldn’t be the same without their furry companion. If you can relate, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winchester: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers an organised and user-friendly area for you to plan new journeys, resume previous ones, or keep track of your travel arrangements. Here, you can easily find the properties you’ve saved or booked, sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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)
  • Bear Trace Golf Course (8.5 mi / 13.7 km)
  • Lakewood Golf & Country Club (15.1 mi / 24.3 km)
  • May Prairie Natural Area (20.4 mi / 32.8 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 (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)
  • The Caverns (19.1 mi / 30.7 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 rental accommodation in Winchester?
The most desirable types of holiday 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 holiday rental 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 rentals 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 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 holiday 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 holiday 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 holiday 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 holiday rentals 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 rentals in Winchester that welcome kids?
Winchester has 42 family-friendly holiday 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 holiday rentals 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 rentals 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 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 holiday homes with WiFi in Winchester. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Winchester?
Work out your travel dates and then use our filter tool to look for holiday rentals with air conditioning in Winchester on Vrbo. With 42 air-conditioned properties on offer here, you can look forward to a comfy and cool stay.
How old do you have to be to rent a holiday rental in Winchester?
The minimum required age is generally 16, 18 or 21. It can change from one property to another on Vrbo, so look at the rules of your chosen Winchester holiday home before booking.
How long can I rent a holiday rental in Winchester for?
The amount of time you can rent a Winchester holiday rental for is down to the property. Simply tap in your preferred travel dates to view available options offering longer term stays. They come with everything you need to make your extended getaway more convenient and comfortable, such as kitchens and air conditioning. Some Vrbo holiday properties may also offer weekly or monthly discounts, so you can hang around longer for less.

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