Winchester holiday lettings

We found 258 holiday rentals — enter your dates for availability

Select from 117 homes, 12 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:26 Dec - 2 Jan

Image gallery for The Bright House is a newly constructed house in the Sewanee Village District.

Living area
10 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)

The Bright House is a newly constructed house in the Sewanee Village District.

Sewanee, TN

8% off
Price is £2,822
for 7 nights, 1 home
£403 per night
includes taxes & fees
The Bright House is a newly constructed house in the Sewanee Village District.

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Find out more about Winchester

Find out more about Winchester

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)
  • 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)
  • Bigfoot Adventure TN Zipline (20.8 mi / 33.4 km)
  • Hammers (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 (9.2 mi / 14.8 km)
  • Tims Ford Lake (9.4 mi / 15.1 km)
  • Lake Cheston (10.4 mi / 16.8 km)
  • Clifftops Lake (14.2 mi / 22.8 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 best area to stay in Winchester when booking a holiday rental?
When considering a holiday rental in Winchester, Tennessee, a popular area to stay is the charming downtown district. This vibrant neighbourhood is not only picturesque but also offers a delightful mix of local shops, cafes, and restaurants, making it an ideal spot for those who enjoy exploring on foot. In addition to the welcoming atmosphere, you'll find the stunning Franklin County Courthouse, a lovely historic building that adds character to the area.

Another appealing option is the area around Tims Ford State Park, which is great for nature enthusiasts. With numerous rental properties available in this vicinity, you'll have easy access to outdoor activities such as hiking, fishing, and boating on Tims Ford Lake. The park's scenic beauty and recreational opportunities make it a fantastic choice for families and those looking to unwind in a serene setting.
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.
Where are the best areas for renting a beach house in Winchester?
In Winchester, Tennessee, the best areas for renting a beach house are primarily found around Tims Ford Lake, which is renowned for its picturesque waterfront and recreational opportunities. The region offers a variety of holiday rentals that cater to different group sizes, including charming lakeside cabins and spacious homes complete with private docks for easy access to the water. Many of these properties come with amenities such as outdoor decks, barbeque grills, and fully equipped kitchens, superb for enjoying meals while taking in the stunning lake views.

The area surrounding the Tims Ford State Park is particularly appealing, as it features beautiful nature trails, picnic areas, and swimming spots. Rentals here often have spacious living areas, multiple bedrooms, and outdoor spaces ideal for family gatherings or relaxing after a day of swimming and boating. Visitors can expect to find properties with amenities like fire pits for evening gatherings, kayaks or canoes for exploring the lake, and some even offer sandy beach areas for sunbathing.
What is the most popular type of holiday rental accomodation in Winchester?
In Winchester, holiday houses are the most popular type of rental, with around 106 available throughout the area. These homes often come with multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking to enjoy a comfortable stay. Additionally, there are about 19 cabins and 12 cottages, which provide a more rustic experience, often featuring unique architectural styles and natural surroundings. For those seeking more compact options, several apartments and chalets can also be found, typically offering essential amenities such as kitchen facilities and cosy living areas.
Are there any family house rentals in Winchester?
In Winchester, Tennessee, there are numerous family-friendly house rentals available, with around 102 properties to choose from. Neighbourhoods such as the historic downtown area and the surrounding suburban streets provide a great selection of homes suited for families. Visitors can expect spacious living areas, fully equipped kitchens, and outdoor spaces like patios or gardens for children to enjoy.

Many of these homes come with amenities such as Wi-Fi and laundry facilities, ensuring a convenient and comfortable stay. The locale is also close to attractions like the beautiful Tims Ford Lake, great for outdoor activities such as fishing and boating, as well as parks ideal for picnics and playdates.
Can I rent a holiday home with a pool or hot tub in Winchester?
In Winchester, Tennessee, there are plenty of holiday homes available for rent that come with pools and hot tubs, with around 40 options to choose from. This charming town offers a variety of neighbourhoods where these properties can be found, each providing a special environment. Many rentals feature private pools and hot tubs, superb for relaxation after a day of exploring the natural beauty of the area.
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, Tennessee, there are numerous pet-friendly house rentals available, offering a variety of amenities to cater to travellers with pets. Many of these rentals provide spacious backyards, ensuring a comfortable environment for pets to roam freely. Expect to find well-equipped kitchens, laundry facilities, and outdoor spaces such as patios or decks, superb for enjoying the pleasant Tennessee weather.
Are there any remote work holiday rentals in Winchester?
In Winchester, Tennessee, there are numerous options for remote work holiday rentals, with around 129 available throughout the area. These properties cater specifically to the needs of remote workers, offering amenities such as dedicated office spaces, reliable Wi-Fi, and comfortable workstations equipped with desks and ergonomic chairs. Many rentals also include additional features like computer monitors and safes for added convenience and security. 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 kitchens, free Wi-Fi, cookware and dishware, microwaves, and refrigerators. These amenities are typically found in the various holiday rentals available in the area, suiting travellers who appreciate the convenience of preparing their own meals and staying connected during their visit.
When is the best time to visit Winchester for a holiday rental?
The most popular time to visit Winchester is during the peak season from May to July. This period is particularly vibrant, as it welcomes a flurry of tourists eager to immerse themselves in the local culture and enjoy outdoor activities. With temperatures typically ranging from the mid-20s to low 30s Celsius, visitors can comfortably explore the picturesque landscapes and historic sites in the area.

July stands out as the highlight of the season, offering an array of festivals and events that celebrate the community's rich heritage. Whether you're wandering through the charming downtown area or engaging in outdoor adventures, you'll find plenty of opportunities to connect with fellow travellers and experience the region's lively atmosphere.

For those seeking a more budget-friendly option, consider planning your visit in November. This month presents a wonderful opportunity to enjoy the tranquillity of Winchester, with fewer crowds and the chance to witness the beauty of autumn as the leaves change colour. The cooler temperatures, generally in the teens Celsius, provide a refreshing backdrop for leisurely hikes and scenic drives.
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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