Winchester holiday lettings

We found 270 holiday rentals — enter your dates for availability

Select from 116 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.

Holiday rentals with weekly discounts – Winchester

Showing deals for:11 Sept - 18 Sept

Image gallery for Lakeside Family Escape-Modern log home in secluded cove w/pvt. dock, Sleeps 12

Lake
10 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)

Lakeside Family Escape-Modern log home in secluded cove w/pvt. dock, Sleeps 12

Lynchburg

7% off
Price is £2,284
for 7 nights, 1 home
£326 per night
includes taxes & fees
Lakeside Family Escape-Modern log home in secluded cove w/pvt. dock, Sleeps 12

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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.

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.

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

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.

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)
  • Short Springs Natural Area (15.4 mi / 24.8 km)
  • Hammers (0.1 mi / 0.1 km)
  • Bear Trace Golf Course (8.5 mi / 13.7 km)
  • Sewanee Golf and Tennis Club (11.3 mi / 18.2 km)
  • Arnold Golf Course (12.1 mi / 19.4 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)
  • 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)
  • Great Stage Park (20 mi / 32.3 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 best area to stay in Winchester when booking a holiday rental?
When considering a holiday rental in Winchester, Tennessee, the downtown area is an excellent choice. This vibrant neighbourhood offers a charming small-town atmosphere with a variety of local shops, restaurants, and cafes that reflect the community's welcoming spirit. One of the highlights of staying in this area is the beautiful Tims Ford Lake, which is superb for outdoor enthusiasts looking to enjoy activities such as fishing, boating, or simply relaxing by the water. Additionally, the nearby Old Jail Museum provides a fascinating glimpse into local history and is a great spot for those interested in heritage and culture.

Another noteworthy option is the area around the Winchester Golf Club, which not only attracts golf enthusiasts but also offers stunning views and a serene environment. This part of Winchester is surrounded by lush greenery and is superb for leisurely walks or picnics. With a range of properties available, from charming cottages to spacious family homes, visitors can find accommodations that suit their needs while enjoying the best that Winchester has to offer.
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.
What is the most popular type of holiday rental accomodation in Winchester?
In Winchester, holiday houses are the most popular type of holiday rental, with around 380 available throughout the area. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor areas great for relaxation. Many are located in serene neighbourhoods, allowing guests to enjoy the peaceful surroundings. Additionally, there are about 72 cabins, which offer a rustic charm and often include amenities like fireplaces and nature views, ideal for a cozy getaway. For those seeking a more quaint experience, around 40 cottages are also available, providing a charming and homely feel. Apartments, while less common, number about 32 and generally include essential amenities for a comfortable stay.
Are there any family house rentals in Winchester?
In Winchester, Tennessee, there are numerous family-friendly house rentals available, with around 99 options to choose from. This charming town offers a variety of properties, often featuring spacious living areas, full kitchens great for preparing family meals, and comfortable outdoor spaces for children to enjoy. Many homes also come equipped with essential amenities such as Wi-Fi and air conditioning, ensuring a pleasant stay for visitors.

The local area provides opportunities for exploration, with nearby attractions including the scenic Tims Ford Lake, ideal for boating and fishing, and the picturesque Tims Ford State Park, which offers hiking trails and picnic spots for those keen on outdoor activities. Additionally, the vibrant downtown area of Winchester is home to quaint shops and restaurants, making it a delightful place for families to experience local culture.
Can I rent a holiday home with a pool or hot tub in Winchester?
In Winchester, Tennessee, there are a variety of holiday homes available for rent that feature pools and hot tubs, with around 39 options to choose from. This charming town is located between scenic lakes and rolling hills, making it an inviting destination for travellers seeking relaxation and outdoor activities.

Many of the available properties come with amenities such as private pools, hot tubs, and spacious outdoor areas great for gatherings or family fun. Inside, you can expect fully equipped kitchens, comfortable living spaces, and often multiple bedrooms, suiting groups or families.
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 pet-friendly house rentals in Winchester?
In Winchester, there are several pet-friendly house rentals available, with around 37 options to choose from. Many of these properties come equipped with amenities that cater to both human and furry guests, including spacious outdoor areas for pets to roam, fully equipped kitchens for home-cooked meals, and comfortable living spaces for relaxation.

The town features a number of parks and green spaces, such as the beautiful Tims Ford State Park, where visitors can enjoy hiking trails, picnic areas, and opportunities for fishing and boating, making it a great spot for those travelling with pets. Additionally, the surrounding areas offer scenic views and a tranquil atmosphere, ideal for a peaceful getaway with your four-legged companions.
Are there any remote work holiday rentals in Winchester?
In Winchester, Tennessee, there are a significant number of remote work-friendly holiday rentals available, with around 496 options to choose from. Many of these accommodations cater specifically to the needs of remote workers, offering amenities such as complimentary Wi-Fi in both rooms and public areas, dedicated desks, and comfortable laptop workspaces.

Travellers can expect a range of properties, from cosy apartments to spacious houses, often featuring modern conveniences like fully equipped kitchens, laundry facilities, and outdoor spaces for relaxation. The town is known for its charming atmosphere and proximity to local attractions, including parks and lakes, which can provide a nice break from work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
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.
What are popular rental amenities in Winchester?
In Winchester, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also feature onsite parking for convenience, as well as decks or patios where travellers can enjoy the pleasant outdoors. A fireplace is a common amenity, providing a cosy atmosphere during cooler evenings, while a coffee and tea maker is typically available for those who enjoy a warm beverage.
When is the best time to visit Winchester for a holiday rental?
The peak season for visiting Winchester, Tennessee, runs from May to July, making it an ideal time for travellers seeking a vibrant holiday experience. With the warm weather and a plethora of outdoor activities, this period attracts travellers, ready to explore the natural beauty and rich history of the area.

July stands out as the most popular month, offering visitors the chance to engage in various outdoor pursuits, such as hiking in the nearby Tims Ford State Park or enjoying leisurely picnics by the lake. The pleasant temperatures, typically ranging from 20 to 32 degrees Celsius, create a comfortable environment for sightseeing and enjoying local events.

If you're looking for a more budget-friendly option, consider planning your trip in November. This month sees fewer tourists, allowing for a more tranquil experience while still providing the opportunity to explore Winchester's charming downtown and surrounding landscapes in a quieter setting.
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.
What are the top attractions in Winchester?
In Winchester, Tennessee, visitors can enjoy a variety of attractions that showcase the area's natural beauty and historical significance. One of the main highlights is the scenic Tims Ford Lake, where outdoor enthusiasts can partake in fishing, boating, and hiking along the picturesque trails. The nearby Tims Ford State Park offers camping facilities and picnic areas, making it an ideal spot for families and nature lovers.

The downtown area features charming shops and local eateries, providing a quaint atmosphere to explore. Additionally, the Winchester City Park is a lovely place for leisurely walks and enjoying community events throughout the year. For history buffs, the Old Jail Museum offers insights into the local history and is a fascinating stop.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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