Winchester vacation rentals

We found 264 vacation rentals — enter your dates for availability

Select from 111 homes, 13 cottages, and other vacation rentals in Winchester to find one that's perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include WiFi and a hot tub. No matter what you're looking for, you'll be able to choose a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Winchester

Showing deals for:Jun 19 - Jun 26

Image gallery for Secluded Bluff Cabin, Stargazing Hot Tub & Firepit

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10 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Secluded Bluff Cabin, Stargazing Hot Tub & Firepit

Belvidere

9% off
Price is $361
$2,526 for 7 nights
All fees included
Secluded Bluff Cabin, Stargazing Hot Tub & Firepit

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Find out more about Winchester

Why visit Winchester

  • Outdoor Adventures: Enjoy activities like golfing, hiking, and lakefront recreation at Tims Ford Lake and Winchester City Park.
  • Romantic Getaway: Experience a cozy atmosphere perfect for couples seeking relaxation and scenic views.
  • Historical Exploration: Immerse yourself in local history at Winchester Square, showcasing the town's rich heritage.
  • Charming Accommodations: Choose from a variety of vacation rentals, including cabins and cottages, for a comfortable stay.
  • Family-Friendly Activities: Engage in fun, family-oriented experiences, making it ideal for all ages.

Popular types of accommodation in Winchester

If you're considering a getaway to Winchester, you're in for a treat. Our vacation rentals offer a variety of popular accommodations, including houses, cozy cabins, and charming cottages. Whether you're looking for Winchester rentals, apartment rentals, or hotels in Winchester, we provide detailed information to ensure you find the perfect stay. Experience the beauty of Winchester with accommodations that cater to your needs and preferences.

  • Houses: The top choice for visitors in Winchester, offering spacious settings perfect for families or groups.
  • Cabins: A popular option for those seeking a rustic getaway, surrounded by nature's beauty.
  • Cottages: Ideal for a cozy and charming stay, providing a homey atmosphere.
  • Apartments: A convenient choice for solo travelers or couples, blending comfort with city access.
  • Chalets: A unique lodging choice that combines mountain charm with modern amenities.**

Top attractions in Winchester

Winchester, Tennessee, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. The area boasts beautiful islands, marine parks, and marinas, providing ample opportunities for beach and family experiences. Enjoy activities like golfing and outdoor adventures, and explore nearby vacation rentals for a comfortable stay. Whether you're looking to relax or embark on exciting excursions, Winchester has something for everyone.

  • Tim's Ford Marina: Experience the thrill of adventure at Tim's Ford Marina, where you can enjoy water activities, beach outings, and outdoor fun. Its picturesque setting makes it perfect for relaxation and exploration.
  • Twin Creeks Marina: Twin Creeks Marina is a family-friendly marine park offering a variety of adventures. Engage in fun activities and create lasting memories with loved ones in this vibrant atmosphere.
  • Bear Trace Golf Course: This beautiful golf course, designed by Jack Nicklaus, provides a challenging yet enjoyable golfing experience amidst stunning natural scenery. Perfect for golf enthusiasts looking to unwind.

Things to do recommended for couples

Discover the charm of Winchester, Tennessee, with a scenic picnic at the beautiful Tims Ford State Park or enjoy a romantic evening stroll around the historic downtown square. Don't miss wine tasting at local vineyards, perfect for creating lasting memories together.

Things to do recommended for families

Families visiting Winchester can explore the scenic Tims Ford State Park, perfect for hiking and picnicking. The nearby Tim's Ford Marina offers fun boat rentals, and the children can enjoy the interactive exhibits at the local Children's Museum, making for a memorable family trip.

Things to do recommended for groups

Groups visiting Winchester can enjoy a guided tour of the historic Old Jail Museum, take part in a fun team-building scavenger hunt around the charming downtown, and savor local flavors at the annual Southern Festival of Books, celebrating regional authors and culinary delights.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, or pets, or if you're considering longer stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winchester with a group: Think about how many bedrooms you require, as well as additional features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winchester: For many families, a getaway isn't truly fulfilling without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of your family feel at home.
  • Planning for a long term stay visiting Winchester: If you're in search of vacation 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 including amenities like parking, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Winchester

Winchester, Tennessee, offers a delightful blend of outdoor adventures and historical charm. Explore the serene Tims Ford Lake for lakefront recreation, unwind at the scenic Winchester City Park, and immerse yourself in local history at Winchester Square. With its friendly atmosphere and romantic vibes, this city is perfect for families and couples alike, providing a unique experience that showcases the beauty and culture of the region.

  • Sewanee: Nestled 11 miles from Winchester, Sewanee is renowned for its stunning outdoor scenery and romantic atmosphere. This charming city is home to the historic Sewanee: The University of the South, offering visitors a glimpse into its beautiful architecture and lush campus. Outdoor enthusiasts can explore the nearby hiking trails and recreational areas, while the picturesque lake and the expansive South Cumberland State Park provide ample opportunities for adventure and relaxation. Sewanee is perfect for those seeking a serene getaway with a touch of academic charm.
  • Decherd: Located just 2 miles from Winchester, Decherd is a delightful city that boasts captivating outdoor experiences and scenic landscapes. Visitors can enjoy recreational parks and hiking trails, making it ideal for nature lovers. The area features a beautiful lake and is in close proximity to the historic college university and the stunning national state park. Decherd offers a quaint, small-town feel while providing access to exciting outdoor activities, making it a perfect stop for a romantic day trip or an adventurous outing.
  • Tullahoma: Situated 13 miles from Winchester, Tullahoma is a vibrant city filled with outdoor charm and scenic views. Known for its recreational areas, campgrounds, and hiking trails, Tullahoma is a haven for those who appreciate nature. The city also features a picturesque lake and a national state park, providing endless opportunities for exploration. Additionally, the local museum adds a cultural touch, making Tullahoma an engaging destination for visitors seeking both adventure and history.

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 SunnyAverageSlightly High
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 SunnyAverageAverage
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 a breeze

Are you hoping to save money on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that meets your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers an easy-to-use platform for planning your next adventures, allowing you to start fresh, continue from where you paused, or manage your travel arrangements. You can find your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Travel to charming Winchester

The lake and other outdoor surroundings create an inviting atmosphere in Winchester. Travelers like the theme park, boating and university setting in this romantic and welcoming city. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Winchester

Are you hoping to discover top things to see and do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Winchester a fun spot to vacation. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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)
  • May Prairie Natural Area (20.4 mi / 32.8 km)

Exploring the natural landscape of Winchester

Whether you're an active traveler or just want to take in the scenery, Winchester is a great spot to appreciate mother nature. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Tims Ford (9.2 mi / 14.8 km)
  • Tims Ford Lake (9.4 mi / 15.1 km)
  • Lake Cheston (10.3 mi / 16.7 km)
  • Walls of Jericho Hiking Trailhead (14.6 mi / 23.4 km)
  • Walls of Jericho Horseback Trailhead (15.4 mi / 24.8 km)
  • Rutledge Falls (16.4 mi / 26.3 km)

Traveling to and around Winchester

The nearest airport is in Chattanooga Metropolitan Airport (CHA), located 52.8 mi (85 km) from the city center. If you can't find a flight that works for your travel itinerary, 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, Tennessee, United States of America when booking a vacation rental?
When looking for the best area to stay in Winchester, Tennessee, for a vacation rental, consider the charming neighborhoods surrounding the picturesque Tims Ford Lake. This area not only offers beautiful waterfront views but also provides easy access to a variety of outdoor activities. Here, you can enjoy hiking, fishing, and boating, making it an ideal spot for nature lovers and families looking to unwind.

Another attractive neighborhood is downtown Winchester, where you can immerse yourself in the local culture. This area features quaint shops and delightful dining options, giving you a taste of the community's hospitality. Nearby, you'll find the historic Franklin County Courthouse, which adds a touch of history to your visit.

There are numerous vacation rental options available in both areas, ensuring that you'll find something that suits your style and budget.
How much does it cost to rent a vacation home in Winchester?
Prices for vacation 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 vacation 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?
For renting a beach house in Winchester, Tennessee, travelers should consider the area around Tims Ford Lake, which is popular for water activities and has several vacation rental options nearby. The lakeside properties often come with amenities such as private docks, spacious decks, and outdoor grills, making them great for families and groups looking to enjoy a lakefront experience. Many of these rentals also feature fully equipped kitchens, allowing guests to prepare meals while enjoying views of the water.

The surrounding area offers opportunities for boating, fishing, and swimming, with easy access to the Tims Ford State Park, which provides hiking trails and picnic areas. Some properties may even include access to community amenities such as swimming pools and recreational facilities.
What is the most popular type of vacation rental accomodation in Winchester?
In Winchester, vacation houses are the most popular type of rental, with about 95 available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups seeking comfort and convenience. Additionally, there are around 18 cabins and 10 cottages available, providing a more rustic experience with charming settings often surrounded by nature.
Are there any family house rentals in Winchester?
In Winchester, Tennessee, there are numerous family-friendly house rentals available, with around 99 options spread throughout the area. Families can find spacious homes in neighborhoods that provide easy access to local parks and recreational activities. Many of these properties come equipped with essential amenities such as full kitchens, ensuring that preparing meals together is convenient and enjoyable. Guests can also expect cozy living spaces, often featuring outdoor areas great for kids to play or for family gatherings.

Visitors will appreciate the proximity to places like Tims Ford Lake, where families can enjoy water activities such as fishing, boating, and swimming. Additionally, the scenic Tims Ford State Park offers hiking trails and picnic spots, making it an ideal destination for outdoor adventures.
Can I rent a vacation home with a pool or hot tub in Winchester?
In Winchester, Tennessee, there are several vacation homes available for rent that feature pools and hot tubs, with around 39 options to choose from. This charming town offers a range of properties in various neighborhoods, providing travelers with ample choices for their getaway. Many of these rentals come equipped with private pools, hot tubs, and outdoor spaces designed for relaxation and entertainment. Guests can also expect amenities such as fully equipped kitchens, spacious living areas, and sometimes even game rooms or outdoor patios for gatherings.
Can I find long-stay vacation rentals in Winchester?
A long-stay vacation rental in Winchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Winchester?
In Winchester, Tennessee, there are several pet-friendly house rentals available, providing a welcoming environment for travelers with pets. Many of these rentals offer amenities such as spacious yards, fully equipped kitchens, and cozy living areas, allowing guests to relax comfortably with their furry companions. The properties often feature outdoor spaces where pets can play, and some may even come with pet-friendly furnishings and easy access to nearby parks or walking trails.

The surrounding area offers opportunities for outdoor activities, including hiking and exploring the scenic beauty of the region. Whether you're looking for a charming cottage or a spacious family home, Winchester's vacation rentals cater to a variety of needs, ensuring a pleasant stay for both you and your pets. See all pet-friendly rentals in Winchester.
Are there any remote work vacation rentals in Winchester?
In Winchester, Tennessee, there are a variety of remote work vacation rentals available, with around 124 options for travelers seeking a conducive environment for productivity. Many of these properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated office spaces, and comfortable work desks, allowing guests to seamlessly blend work and leisure.

Travelers can expect cozy homes with spacious living areas and well-stocked kitchens, ideal for longer stays. The city itself offers a charming small-town atmosphere, and nearby parks provide opportunities for outdoor breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winchester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winchester with parking available—perfect for families or travelers 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 vacation rental amenities typically include kitchens, allowing travelers to prepare their own meals during their stay. Many rentals also feature onsite parking for convenience, as well as decks or patios for enjoying the outdoors. A cozy fireplace is often a welcome addition, providing warmth and ambiance, especially during cooler months. Additionally, rentals frequently come equipped with coffee and tea makers, ensuring guests can enjoy their favorite hot beverages at any time.
When is the best time to visit Winchester for a vacation rental?
The peak season in Winchester runs from May to July, making it an ideal time for travelers seeking vibrant outdoor experiences. During these months, visitors can enjoy a variety of activities, including hiking and fishing in the beautiful landscapes that surround the area. July, in particular, stands out as the most popular month, drawing in crowds who want to savor the warm weather and partake in local festivities.

The climate during this time is typically warm, with temperatures ranging from the mid-60s to low 90s Fahrenheit, creating a pleasant atmosphere for outdoor adventures and sightseeing. Those keen on exploring Winchester's charming downtown or taking leisurely strolls around the picturesque parks will find plenty of opportunities to enjoy the scenery and interact with friendly locals.

However, if you're looking for a more budget-friendly option, consider visiting in November. This month offers a quieter ambiance that allows for a more relaxed experience of the area's natural beauty. Autumn in Winchester brings stunning fall foliage, great for scenic drives and picturesque hikes, without the crowds of peak season.

Ultimately, your choice of when to visit Winchester should reflect your preferences, whether you're drawn to the lively summer atmosphere or the serene beauty of the fall season.
How early should I book a Winchester vacation rental?
Book your Winchester vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winchester, Tennessee, United States of America?
In Winchester, Tennessee, visitors can explore several attractions that highlight the area's natural beauty and historical significance. The Tims Ford State Park is a popular destination, offering outdoor activities such as hiking, fishing, and boating on Tims Ford Lake. Vacation rentals near the park provide easy access to scenic views and recreational opportunities.

The historic downtown area features charming shops, local eateries, and the Franklin County Courthouse, which reflects the town's rich history. Nearby, the Old Jail Museum offers insights into the area's past and is a fun stop for history enthusiasts.

For those interested in aviation, the nearby Arnold Air Force Base has an interesting visitor center that showcases the history of the base and its contributions to aerospace.
Can I change or cancel my Winchester home rental booking on Vrbo?
To find Winchester vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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