Winchester vacation rentals

We found 262 vacation rentals — enter your dates for availability

Select from 111 homes, 10 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:Apr 3 - Apr 10

Image gallery for The Sewanee House: Serene Oasis 5 minutes from Campus

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10 out of 10, Exceptional, (34 reviews)
Exceptional
(34 reviews)

The Sewanee House: Serene Oasis 5 minutes from Campus

Sewanee

9% off
Price is $1,327
$9,287 for 7 nights
All fees included
The Sewanee House: Serene Oasis 5 minutes from Campus

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Find out more about Winchester

Why visit Winchester

  • Outdoor Adventures: Winchester is perfect for hiking, boating, and exploring its scenic marinas and parks.
  • Charming Accommodations: Choose from cozy cabins, quaint cottages, or spacious homes, many of which are pet-friendly.
  • Family-Friendly Activities: Enjoy a variety of fun activities suitable for families and couples alike.
  • Inviting Neighborhoods: Discover vibrant neighborhoods that blend urban culture with recreational fun.
  • Scenic Views: Experience breathtaking landscapes, making it an ideal romantic getaway or relaxing retreat.

Popular types of accommodation in Winchester

Discover the charm of Winchester with our diverse selection of vacation rentals. Whether you’re looking for a cozy cabin, a quaint cottage, or a spacious private vacation home, we have options to suit every traveler. Many of our rentals are pet-friendly and feature outdoor seating for relaxation. Plus, if you’re seeking a splash of fun, you’ll find rentals with pools as well. Explore Winchester's unique accommodations and find your perfect getaway.

  • Houses: The top choice for travelers in Winchester, offering spacious and comfortable settings ideal for families or groups.
  • Cabins: A popular option for those seeking a rustic experience, surrounded by nature and tranquility.
  • Cottages: Charming and cozy, these accommodations provide a homey feel for couples or small families.
  • Apartments: Convenient and often centrally located, perfect for solo travelers or those wanting a more urban stay.
  • Chalets: A delightful choice for those looking for a unique mountain-style retreat with character.**

Top attractions in Winchester

Winchester, Tennessee, is the perfect destination for those seeking outdoor adventures and scenic views. With its charming marinas, beautiful islands, and inviting marine parks, the area offers a variety of attractions ideal for families, couples, and beach lovers alike. Whether you're looking for a romantic getaway or fun family activities, Winchester has something to make your vacation unforgettable.

  • Tim's Ford Marina: Experience the great outdoors at Tim's Ford Marina, where you can enjoy water activities, beach vibes, and adventure amidst stunning lake views. Perfect for boating, fishing, and relaxing in nature.
  • Twin Creeks Marina: A family-friendly destination, Twin Creeks Marina offers exciting adventures on the water. Enjoy boating, fishing, and picnicking while surrounded by beautiful scenery, making it an ideal spot for family outings.
  • Bear Trace Golf Course: This beautiful golf course combines challenging play with picturesque landscapes. Designed by Jack Nicklaus, Bear Trace offers a premier golfing experience amid lush greenery and serene surroundings.

Things to do recommended for couples

Planning a romantic getaway in Winchester? Explore the serene beauty of Tims Ford Lake, where you can enjoy a peaceful picnic or rent a boat for a sunset cruise. Don't forget to stroll through the charming downtown area, filled with unique shops and cozy cafes perfect for couples.

Things to do recommended for families

During your family vacation in Winchester, Tennessee, enjoy a day at Hank Weddington Park for outdoor fun, visit the City of Decherd Babe Ruth Ball Park for some recreational activities, and relax at the Pleasant Grove Public Use Area, perfect for wellness and family bonding.

Things to do recommended for groups

Explore the charm of Winchester by visiting the Jack Daniel's Distillery for a taste of local spirits, shop at Hammers for unique finds, or enjoy family fun at the County Plaza Shopping Center, all while soaking in the vibrant atmosphere of the area.

*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, as a family, bringing your pets along, or planning an extended stay, be sure to filter your search based on your top priorities. Here are some helpful tips for booking on Vrbo.

  • Traveling to Winchester with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with little ones can be a bit tricky. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you'll be to attractions that are family-friendly.
  • Taking your pets with you to Winchester: For many families, a vacation wouldn’t feel complete without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Winchester: If you're in search of vacation rentals that offer 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 include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Winchester

Winchester, Tennessee, is the perfect getaway for those seeking outdoor adventures and romantic scenery. Nestled in Franklin County, this charming city offers a friendly atmosphere ideal for families and couples alike. Explore the beautiful properties and vibrant neighborhoods nearby, where urban culture meets recreational fun. Whether you're hiking in nature or enjoying local attractions, Winchester promises a delightful experience for every traveler.

  • Sewanee: Nestled 11 miles from Winchester, Sewanee is known for its breathtaking outdoor scenery and romantic atmosphere. The town is home to the historic Sewanee: The University of the South, which boasts stunning architecture and beautifully landscaped grounds. Adventurers will enjoy the nearby hiking trails and the serene lake, offering ample opportunities for recreation. Additionally, the expansive South Cumberland State Park provides a perfect backdrop for outdoor activities, making it an ideal destination for nature lovers and those seeking a peaceful retreat.
  • Tullahoma: Located 13 miles from Winchester, Tullahoma is another charming city that captivates visitors with its scenic vistas and outdoor experiences. The town features inviting recreational areas and campgrounds, perfect for family outings and weekend getaways. Outdoor enthusiasts can explore the local hiking trails that wind through the picturesque landscape. Tullahoma is also home to a beautiful lake and a national state park, along with a local museum that provides a glimpse into the region's history and culture, making it a well-rounded stop on your vacation.
  • Decherd: Just 2 miles away from Winchester, Decherd offers a quaint and welcoming atmosphere with a focus on outdoor enjoyment. Visitors can explore local educational venues and recreational areas while enjoying the scenic beauty of the nearby lake and historic college university. The national state park is also within reach, providing opportunities for hiking and camping. Decherd's combination of natural beauty and community spirit makes it a delightful destination for anyone looking to unwind and connect with nature.

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 save on your upcoming trip? Being flexible with your travel dates can help, as prices often vary. Additionally, planning for a longer stay typically leads to significant savings. To discover the perfect Vrbo rental that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you'll receive OneKeyCash on the full booking amount. Being the organizer certainly has its benefits. Enroll in our One Key rewards program to unlock exclusive savings for members and start earning OneKeyCash on qualifying stays. Sign up today and begin your earning journey.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new vacations, pick up where you left off, and manage your travel arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using 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)
  • Sewanee Golf and Tennis Club (11.3 mi / 18.2 km)
  • Short Springs Natural Area (15.4 mi / 24.8 km)
  • Bigfoot Adventure TN Zipline (20.8 mi / 33.4 km)
  • Hammers (0.1 mi / 0.1 km)
  • Lakewood Golf & Country Club (15.1 mi / 24.3 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 (10.4 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)

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 when booking a vacation rental?
When considering a vacation rental in Winchester, Tennessee, a popular area to stay is near the historic downtown district. This charming neighborhood offers a delightful mix of quaint shops, local eateries, and cultural experiences, making it an ideal spot for visitors who want to immerse themselves in the local vibe. Here, you can easily explore the beautifully preserved architecture and enjoy the vibrant community atmosphere.

A highlight of staying in downtown Winchester is the proximity to the Old Jail Museum, where you can delve into the area's history and learn about its intriguing past. Additionally, the nearby Winchester City Park provides a lovely outdoor space for relaxation and recreation, featuring walking trails, picnic areas, and scenic views.

Another great option is the area surrounding Tims Ford Lake, which is great for those who enjoy outdoor activities. This picturesque location offers ample opportunities for fishing, boating, and hiking, making it a haven for nature enthusiasts. The lake is a significant attraction that draws visitors for its stunning beauty and recreational options.
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 a popular destination for water activities and relaxation. The neighborhoods along the lake, such as those near Tims Ford State Park, offer a variety of vacation rentals that provide beautiful lake views and direct access to the water. Many properties in this region come with amenities such as private docks, spacious decks for outdoor entertaining, and fully equipped kitchens, making them ideal for families or groups looking to enjoy a lakeside getaway.

Additionally, the Tims Ford State Park area features cabins and homes that allow guests to immerse themselves in nature while still being close to recreational activities. These rentals often include features like fire pits, picnic areas, and access to hiking trails, providing plenty of opportunities for outdoor adventures. Find your rental near the beach in Winchester.
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 104 available throughout the area. These homes are often situated in peaceful neighborhoods, providing a comfortable base for travelers looking to explore local attractions such as the historic downtown and nearby parks. Most vacation houses come equipped with multiple bedrooms, fully stocked kitchens, and spacious living areas, making them great for families or groups.

Additionally, there are around 18 cabins and 12 cottages available, offering a rustic charm that appeals to those seeking a more nature-oriented experience. These properties typically feature outdoor spaces and proximity to natural settings, ideal for activities like hiking or fishing. While there are several apartments and chalets, they are less common compared to the abundance of vacation houses.
Are there any family house rentals in Winchester?
In Winchester, Tennessee, there are numerous family-friendly house rentals available, with around 103 options to choose from. This charming town offers a variety of accommodations suitable for families, often featuring spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for children to play.

Visitors can explore local attractions such as the beautiful Tims Ford Lake, known for its recreational activities like fishing, boating, and hiking. Many properties come with amenities like Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable and convenient stay for all family members. See all family-friendly rentals in Winchester.
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 peaceful atmosphere, superb for relaxation. Many of these properties come equipped with private pools, hot tubs, and spacious outdoor areas, ideal for enjoying the beautiful Tennessee weather. Inside, travelers can expect amenities such as fully equipped kitchens, comfortable living spaces, and often multiple bedrooms, making them suitable for families or groups. Find your rental in Winchester with a pool or a hot tub.
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 numerous pet-friendly house rentals available, with around 42 options for travelers to choose from. Many of these properties feature spacious living areas, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups traveling with pets. Some rentals may offer amenities such as fenced yards, which provide a safe space for pets to roam and play.

The area surrounding Winchester is rich in natural beauty, with nearby parks and recreational areas superb for outdoor activities. The Tims Ford State Park is a popular destination, offering scenic trails, fishing spots, and picnic areas where pets are welcome, allowing for enjoyable outings with your furry companions. See all pet-friendly rentals in Winchester.
Are there any remote work vacation rentals in Winchester?
In Winchester, Tennessee, there are numerous vacation rentals suitable for remote work, with around 127 options available. Travelers can expect properties equipped with essential amenities for productivity, including high-speed Wi-Fi, dedicated workspaces such as desks and comfortable chairs, and even features like computer monitors in some rentals. Many homes also provide a safe for securing personal belongings, creating a conducive environment for both work and relaxation.

The area is known for its scenic beauty, with nearby attractions like Tims Ford Lake offering opportunities for outdoor activities after work hours. Rentals in this region often come with additional comforts such as fully equipped kitchens, spacious living areas, and outdoor spaces, allowing guests to unwind in a peaceful setting while maintaining their work commitments. 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 include WiFi, kitchens, and coffee/tea makers, making it convenient for guests to stay connected and prepare their own meals. Many rentals also feature patios, offering a space to relax outdoors, and blenders for those looking to whip up smoothies or other beverages.
When is the best time to visit Winchester for a vacation rental?
The best time to visit Winchester for a vacation rental is during the peak season from May to July. This lively period attracts travelers looking to enjoy the warm Southern sunshine and partake in various outdoor activities, including hiking and exploring the stunning landscapes of the area. With temperatures typically ranging from the mid-60s to the high 80s Fahrenheit, visitors can comfortably enjoy sightseeing and local attractions.

July stands out as the most popular month, bringing a vibrant energy to Winchester. Visitors can engage in the local culture, attend seasonal events, and participate in outdoor festivals that showcase the region's charm. Whether you're wandering through the picturesque downtown or indulging in local cuisine, there's no shortage of experiences to savor.

For those looking for a more budget-friendly option, November is a wonderful time to visit. This month offers a quieter atmosphere, allowing for a more relaxed exploration of Winchester and its surrounding areas.
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?
In Winchester, Tennessee, visitors can enjoy a variety of attractions that showcase the area's natural beauty and cultural heritage. The scenic Tims Ford Lake is a major highlight, offering opportunities for fishing, boating, and hiking along its picturesque shores. Nearby, Tims Ford State Park features numerous trails and picnic areas, great for outdoor enthusiasts looking to explore the Tennessee landscape.

In the downtown area, travelers can experience local history at the Winchester Depot, which provides insights into the region's past. The annual Southern Middle Tennessee Fair also attracts visitors, featuring rides, games, and local agricultural exhibits. For those interested in music, the area often hosts live performances and events, reflecting the rich musical heritage of Tennessee.
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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