Winchester vacation rentals

We found 254 vacation rentals — enter your dates for availability

Select from 115 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.

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Find out more about Winchester

Why visit Winchester

  1. Outdoor Adventures: Winchester is perfect for nature lovers with local parks, scenic lakes, and nearby national parks.
  2. Unique Distillery Tours: Experience local flavors with engaging distillery tours showcasing Tennessee's rich heritage.
  3. Picturesque Waterfalls: Discover stunning waterfalls that offer breathtaking views and great photo opportunities.
  4. Barefoot Beach Experience: Enjoy a relaxing day at a unique beach where you can walk barefoot and unwind.
  5. Charming Accommodations: Choose from cozy vacation homes, charming cottages, and rustic log cabins for a delightful stay.

Popular types of accommodation in Winchester

Planning a getaway to Winchester? You're in for a treat! Discover the charm of houses, cozy cabins, and quaint cottages that make this destination special. Whether you're seeking a rustic log cabin or a modern villa, Winchester offers a variety of vacation rentals to suit every taste. Start your adventure by exploring the inviting options available, including the unique Western Inn, and make your stay unforgettable!

  • Houses: The top choice for travelers in Winchester, offering spacious and comfortable accommodations perfect for families or groups.
  • Cabins: A popular option for those seeking a rustic experience, these charming retreats provide a cozy atmosphere surrounded by nature.
  • Cottages: Ideal for couples or small families, these quaint homes offer a homely feel with a touch of charm.
  • Apartments: A convenient choice for travelers wanting a modern living space with amenities, perfect for longer stays.
  • Caravan Parks: Great for outdoor enthusiasts, these parks provide a unique camping experience with various facilities.**

Top attractions in Winchester

Winchester, Tennessee, is a perfect destination for outdoor enthusiasts and those seeking romance. Explore local parks, scenic lakes, and the nearby national and state parks for a family-friendly eco-adventure. Don’t miss out on distillery tours, picturesque waterfalls, and a unique barefoot beach experience. Whether you're traveling solo or with loved ones, Winchester offers a delightful blend of nature and charm for an unforgettable getaway.

  1. Tim's Ford Marina: Experience adventure and outdoor fun at Tim's Ford Marina, where you can enjoy boating, fishing, and beach vibes in a picturesque setting right within Winchester.
  2. Tims Ford Lake: A romantic getaway awaits at Tims Ford Lake, located 9 miles away, offering stunning scenery, outdoor activities, and a serene beach atmosphere perfect for picnics and relaxation.
  3. Tims Ford State Park: Just 9 miles from Winchester, Tims Ford State Park invites you to explore its adventurous trails, breathtaking views, and abundant outdoor activities amidst nature’s beauty.

Things to do recommended for couples

For a romantic getaway in Winchester, consider visiting Great Stage Park, located 20 miles away. Enjoy a lively music concert that sets the perfect atmosphere for couples, filled with entertainment vibes and a chance to create lasting memories together.

Things to do recommended for families

In Winchester, Tennessee, families can explore the serene South Cumberland State Park, just 19 miles away, perfect for outdoor fun and relaxation. Additionally, the Short Springs Natural Area, located 15 miles from Winchester, offers beautiful scenery and a peaceful environment for a delightful family outing.

Things to do recommended for groups

Explore Hammers for unique finds, then venture to Jack Daniel's Distillery for a taste of local spirits and entertainment. Don't miss the Sewanee Golf and Tennis Club for outdoor sports fun with friends, just 11 miles away.

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

When planning your trip, whether you're traveling with a group, enjoying a family getaway, bringing along your pets, or seeking extended stays, it's important to prioritize your preferences. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winchester with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, thinking about your closeness to family-friendly attractions can be beneficial.
  • Taking your pets with you to Winchester: For many families, a vacation wouldn't feel complete without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winchester: If you're searching for vacation rentals that offer great deals 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 even a private pool in your search criteria.

Where to stay in Winchester

Winchester, Tennessee, is a delightful getaway that offers stunning views and a perfect blend of outdoor adventures and romantic scenery. Explore the family-friendly atmosphere and enjoy excursions in the heart of Middle Tennessee. Whether you're seeking a charming country escape or a recreational retreat, Winchester and its nearby regions promise a wonderful experience filled with friendly locals and rich history.

  • Monteagle: Located 16 miles from Winchester, Monteagle is a charming city that invites travelers to immerse themselves in outdoor adventures and stunning natural scenery. Known for its recreational areas and hiking trails, Monteagle offers a perfect escape for nature lovers and adventure enthusiasts alike. Visitors can explore the nearby national state park and enjoy picturesque views around the local lake. With its tranquil parks and abundant opportunities for exploration, Monteagle is an ideal spot for those seeking both relaxation and activity.
  • Sewanee: Just 11 miles from Winchester, Sewanee is a picturesque city renowned for its romantic atmosphere and outdoor experiences. The historic college university adds a unique charm to the area, making it a great destination for education and cultural exploration. Visitors can take advantage of the hiking trails and scenic spots around the local lake and national state park, providing ample opportunities for breathtaking views and memorable outings. Sewanee is perfect for couples and families looking to enjoy the beauty of nature while indulging in the area's rich history.
  • Manchester: Situated 20 miles from Winchester, Manchester is a vibrant city known for its outdoor experiences and lively music scene. The area is filled with recreational opportunities, from exploring parks to attending music concerts. With its proximity to local lakes and a national state park, Manchester provides a wealth of activities for those looking to engage with nature. Whether you're hiking scenic trails or enjoying a community event, Manchester is a fantastic destination for travelers seeking adventure and memorable experiences.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 High
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 Low
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 LowSlightly High
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, booking a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the best options for your needs!

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you’ll earn OneKeyCash™ on your entire booking. Being the organizer certainly has its perks! Enroll in our One Key rewards program to unlock exclusive savings for members and earn OneKeyCash™ on qualifying stays. Sign up today to start reaping the rewards!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers an easy-to-use platform for planning your travels. You can effortlessly create new trips, continue from where you last stopped, or organize your existing plans all in one place. Here, you’ll find your saved or booked properties neatly sorted into categories: Potential, Upcoming, or Current Trips. To begin using Trip Boards, just visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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)
  • Bear Trace Golf Course (8.5 mi / 13.7 km)
  • Lakewood Golf & Country Club (15.1 mi / 24.3 km)
  • May Prairie Natural Area (20.4 mi / 32.8 km)

Exploring the natural landscape of Winchester

Whether you're 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)
  • Sewanee Natural Bridge (10.9 mi / 17.5 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 most popular type of vacation rental accommodation in Winchester?
Cabins are the most popular style of vacation rental in Winchester, according to our data. Even if you have something bigger or smaller in mind, Vrbo has vacation homes in a variety of shapes and sizes. Browse our many options to find your perfect fit.
How much does it cost to rent a vacation rental in Winchester?
Season, property type and length of stay are some of the conditions that can affect the price of a vacation home. Simply enter your dates of travel to find your perfect match. From comfy cabins to expansive luxury villas, all Vrbo vacation rentals offer unbeatable value.
How much does it cost to rent a beach house in Winchester?
When you travel and the size and style of the property will determine the cost of your beachside stay. Type in your Winchester travel dates to view your available options on Vrbo. Did someone just say "private pool"? Use our filters to select the features and amenities you want in your rental.
Are there pet-friendly vacation rentals in Winchester?
Happily, yes. You can choose from 92 vacation rentals that allow pets in Winchester on Vrbo. Our cuddly best friends deserve a break too, so simply use our search function for pet-friendly vacation rentals to find a perfect property where your pooch can join in the fun.
Can I rent a house with a pool in Winchester?
Pack your swimwear and inflatable flamingo, because there are 29 houses with a private pool in Winchester. Book a stay at one of these terrific vacation homes and enjoy a pool day every day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Winchester?
The most popular rental amenities people search for in Winchester are a swimming pool, an electric car charging station and a lake view. Whether you're going on vacation with family, pals or even pets, Vrbo vacation rentals feature the best amenities for beginning new traditions with the people you love.
Are there large group vacation rentals in Winchester?
Pick from 46 properties in Winchester that can accommodate 10 or more guests. Whether you're planning time away with extended family or a special event, there's plenty of space to get your favorite people together under the same roof.
Are there vacation rentals in Winchester that welcome kids?
Winchester has 92 family-friendly vacation rentals to choose from. And tracking down a stay that welcomes children is a breeze with Vrbo's "Properties good for families" filter. On top of having the entire place to yourselves, you'll get perks and conveniences like bunk beds, kitchens and pools.
What are the top attractions for families in Winchester?
Have a day out with the family at Tim's Ford Marina. This major attraction is situated near the heart of Winchester.
Are there one-bedroom vacation rentals in Winchester?
Yes, there are five one-bedroom properties in Winchester to select from. A one-bedroom vacation rental is a wonderful choice if it's just two of you or if you're traveling alone. Toss in more privacy, space and convenience than a regular hotel, and you're sure to have a memorable trip.
Can I find two-bedroom vacation rentals in Winchester?
Choose from nine two-bedroom properties in Winchester. Give your little ones the second room or fill it with a couple of your nearest and dearest friends. There's a spot for whoever's fortunate enough to be joining your journey.
Are there vacation rentals with WiFi in Winchester?
Choose from 55 vacation rentals with WiFi in Winchester. If you want to disconnect from daily life during your trip, but still want to be connected to the web, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Winchester?
Winchester has 92 vacation rentals where you'll be able to unwind in air-conditioned comfort. To find a property on Vrbo featuring this perk, enter your preferred travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Winchester?
It's a good idea to check with the Winchester vacation rental you'd like on Vrbo as the age limit differs. However, it's generally 16, 18 or 21.
How long can I rent a vacation rental in Winchester for?
The amount of time you can rent a Winchester vacation rental for is down to the property. Simply tap in your travel dates to see available options that offer extended stays. They come with everything you need to make your extended vacation more comfortable and enjoyable, such as kitchens and laundries. Some vacation rentals may also offer discounted weekly or monthly prices, so you can stay longer for less money.
Does Vrbo offer discounts for vacation homes in Winchester?
Whether you're after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to find some fabulous deals and discounts on Vrbo. From weekend retreats to extended vacations, we've got the ideal space for your next Winchester escape.

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