Best Vacation Homes in Winchester
House
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
R5,190/Night
7 Nights - R36,336
House
10.0(5 Reviews)
4 Bedrooms
3 Baths
8 Guests
2400.35 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
Air Conditioner
R9,352/Night
7 Nights - R65,463
House
2 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R2,997/Night
7 Nights - R20,977
Cottage
10.0(9 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R2,991/Night
7 Nights - R20,944
Villa
10.0(4 Reviews)
4 Bedrooms
3 Baths
10 Guests
2798.62 ft²
Oceanfront
Hot Tub
Pool
Ocean View
R5,845/Night
7 Nights - R40,914
Cabin
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
Internet
Child Friendly
Designated Smoking Area
R2,823/Night
7 Nights - R19,759
Cabin
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
Pet Friendly- Air Conditioner
- Internet
R3,331/Night
7 Nights - R23,315
Cabin
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pet Friendly
- Internet
- Child Friendly
- Designated Smoking Area
R2,978/Night
7 Nights - R20,847
Winchester Luxury Rentals
House
10 Bedrooms
6 Baths
34 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R36,736/Night
7 Nights - R257,160
R32,118/Night
7 Nights - R224,819
House
5 Bedrooms
4 Baths
16 Guests
39826.47 ft²
- Hot Tub
- Fireplace/Heating
- Air Conditioner
- Internet
R25,074/Night
7 Nights - R175,510
House
10.0(15 Reviews)
6 Bedrooms
5 Baths
22 Guests
6200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R23,187/Night
7 Nights - R162,310
House
10.0(5 Reviews)
3 Bedrooms
2 Baths
14 Guests
75347 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R18,447/Night
7 Nights - R129,124
House
10.0(8 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R18,394/Night
7 Nights - R128,767
House
10.0(52 Reviews)
5 Bedrooms
3 Baths
16 Guests
30677 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R18,073/Night
7 Nights - R126,510
House
10.0(34 Reviews)
5 Bedrooms
4 Baths
16 Guests
3650 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R17,769/Night
7 Nights - R124,383
Winchester Pet Friendly Vacation Rentals
Apartment
9.8(15 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R3,096/Night
7 Nights - R21,675
Apartment
9.6(11 Reviews)
1 Bedroom
1 Bath
2 Guests
398.26 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
R1,969/Night
7 Nights - R13,784
House
9.6(81 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,730/Night
7 Nights - R40,103
House
9.6(7 Reviews)
3 Bedrooms
2 Baths
8 Guests
1797.57 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
R6,467/Night
7 Nights - R45,266
Cabin
9.6(4 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,803/Night
7 Nights - R26,627
Cabin
9.4(21 Reviews)
2 Bedrooms
1 Bath
4 Guests
608 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,593/Night
7 Nights - R39,145
Cabin
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,355/Night
7 Nights - R23,477
House
10.0(84 Reviews)
3 Bedrooms
2 Baths
8 Guests
2200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
R5,899/Night
7 Nights - R41,288
Winchester Large Vacation Homes
House
9.8(18 Reviews)
2 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
R4,182/Night
7 Nights - R29,273
House
10.0(3 Reviews)
1 Bedroom
3 Baths
10 Guests
3003.13 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R6,964/Night
7 Nights - R48,740
New
House
4 Bedrooms
3 Baths
13 Guests
27986 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R16,080/Night
7 Nights - R112,563
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
12 Guests
2992.37 ft²
- Pool
- Balcony/Terrace
- Parking
- Air Conditioner
R6,170/Night
7 Nights - R43,187
New
House
5 Bedrooms
5 Baths
12 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R6,103/Night
7 Nights - R42,717
Cottage
10.0(163 Reviews)
4 Bedrooms
3 Baths
12 Guests
2550 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R7,739/Night
7 Nights - R54,163
House
10.0(90 Reviews)
4 Bedrooms
4 Baths
10 Guests
1798 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R8,379/Night
7 Nights - R58,660
House
10.0(88 Reviews)
4 Bedrooms
3 Baths
12 Guests
1887 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
R6,400/Night
7 Nights - R44,795
Why Choose Rent By Owner for your Winchester Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Winchester
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, allowing you to enjoy the region’s pleasant climate and local events that make Winchester, Tennessee, USA a memorable destination for your next getaway.
Peak Season Highlights
Spring (March to May)
During spring, this destination experiences pleasant weather that is ideal for exploring the scenic beauty and local events in the area.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Fall (September to November)
Autumn offers comfortable temperatures and vibrant foliage, making it a popular time for outdoor activities and enjoying the region’s natural charm.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (December to February)
In winter, the area sees fewer visitors, providing a quieter environment for relaxing stays and exploring local culture without crowds.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
Summer (June to August)
While summer brings warmer weather, it is also the off-peak period when fewer travelers are here, offering more privacy and affordability.
Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F
Weekly Weather Forecast for Winchester
How to Book Your Winchester Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Winchester
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor grilling amenities to host a barbecue in the region’s pleasant weather.
- Relax in a private backyard or patio area perfect for unwinding after exploring here.
- Take advantage of spacious gardens or lawns ideal for outdoor activities and games.
- Make use of a swimming pool or hot tub, common features for outdoor relaxation in this destination.
- Benefit from outdoor furniture that allows you to dine al fresco while enjoying the scenery.
- Discover hiking or walking trails accessible directly from your rental property location.
- Utilize a fire pit or outdoor fireplace to gather with family and friends during cool evenings here.
Top Attractions Around Winchester
What attractions are nearby?
While here, you can enjoy a variety of outdoor activities and local attractions that showcase the charm and natural beauty of the region surrounding Winchester, Tennessee.
Family Activities
- Winchester City Park: Enjoy a day outdoors at this spacious park, perfect for picnics, playground fun, and family-friendly hikes through scenic trails.
- Hampton Station: Explore historic charm with train rides and train-themed activities that delight children and give families a glimpse into the region’s rail history.
- Big Springs Park: Discover this serene park featuring a spring-fed pond, offering fishing, paddle boating, and peaceful picnic spots for memorable family outings.
- Musick’s Campground and Marina: Engage in water-based adventures with boat rentals and lakeside relaxation, ideal for active families seeking outdoor fun near here.
Adult Activities
- Winchester City Park: Spend your day outdoors at the scenic city park, perfect for picnicking, walking, and enjoying local events in this inviting part of the area.
- Apple Barn Winery & Cider House: Experience a taste of the region’s agricultural charm by sampling handcrafted wines and ciders at this celebrated Tennessee winery.
- Johnnie M. Walker Memorial Museum: Dive into local history and culture through engaging exhibits that highlight Winchester’s rich heritage and community stories.
- Multi-Use Sports Complex: Stay active or cheer on local teams at this modern facility offering a range of sports activities perfect for adult enthusiasts visiting here.
Other Places to Stay in Winchester, TN
Franklin County
Expressions
Hammers
Tim's Ford Marina
Tims Ford State Park
Tims Ford Lake
Winchester Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take time to discover the nearby historical sites and scenic spots that highlight the charm of this destination.
- Plan Your Dining Experiences: Savor the regional cuisine at local eateries to truly immerse yourself in the area's culinary culture.
- Choose a Prime Location for Your Vacation Rentals: Opt for accommodations close to key attractions to maximize your sightseeing and relaxation time.
- Experience Seasonal Activities: Engage in outdoor activities or festivals depending on the time of year to make the most of your visit here.
Transportation Options
- Winchester Municipal Airport: You can access regional flights and private aviation services conveniently located near here, making travel to the area straightforward.
- Interstate 24: This major highway runs through the region, providing easy road connectivity for travelers driving from nearby cities and states.
- Local Bus Services: Public transportation options are available within the area, offering an affordable and practical way to navigate locally.
- Taxi and Rideshare Services: Reliable taxi companies and rideshare apps serve here, ensuring convenient transportation for day trips or airport transfers.
Local Customs Options
- Southern Hospitality: You will notice the warm and welcoming spirit that defines the region, making your stay here feel like a true local experience.
- Local Craftsmanship: Appreciate the region’s artisanal traditions, often showcased through handcrafted goods and community-centered markets.
- Traditional Cuisine: Sampling classic Southern dishes is a must, as culinary customs here emphasize hearty, home-cooked flavors rooted in local history.
Participate in seasonal festivals and gatherings that reflect the area's deep-rooted cultural heritage and sense of community.
Frequently Asked Questions About Winchester?
1. What are the top vacation rentals in Winchester?
There are a lot of options in Winchester. If you plan on staying in the Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winchester:
- Tim's Ford Lake Home. Private Boat Dock with Jet Ski Port & 2 Kayaks
- Hickory Hideaway on Tim`s Ford Lake, Boat rental available
- Beautiful Lake Townhouse at Twin Creeks Resort
- Enjoy fireside sunset & walk to movies, shops, restaurants!
- Big Lake Views Tims Ford Lake! Lots of space and great for family get togethers
- Easy Peasy -lakefront home Tim’s Ford Lake -golf cart seats 6, in Twin Creeks
- Beautiful Lake Views at Twin Creeks!
- Million Dollar Views + Luxury + Infinity Deck
- Waterfront Oasis On Tims Ford Lake: Pool/Kayak!
- "Tims Ford Bliss" amazing Lakefront views, private Dock, Beach, Firepit, Fun!
2. How many vacation rentals have private pools in Winchester?
There are 6 vacation rentals with private pools near Winchester. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Winchester are best for families?
If you are looking for a family-friendly vacation home in Winchester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winchester:
4. How many Rentbyowner vacation rentals are available in Winchester?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 288 in the Winchester area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winchester.
5. What is the cancellation policy for vacation rentals in Winchester, Tennessee?
The cancellation policy varies depending on the property owner. You should review the specific listing details or contact the host directly to understand the terms before booking.
6. Are there any additional fees I should be aware of when booking a vacation rental in this region?
Additional fees such as cleaning fees, service charges, or local taxes may apply and are typically detailed in the property listing. It's advisable to read the full description or ask the host for clarification.
7. How do I ensure my reservation at a vacation rental in Winchester, Tennessee, is secure?
Reservations are secured through the trusted booking platform, which offers secure payment options. Confirm the host's reviews and ratings to ensure a reliable stay.
8. What amenities can I expect from vacation rentals here?
Property amenities vary by listing but often include essentials like Wi-Fi, parking, and kitchen facilities. Specific amenities are detailed in each listing — be sure to review them thoroughly.
9. Is there a minimum stay requirement for vacation rentals in this area?
Minimum stay requirements depend on the individual property. You can verify this during the booking process or by contacting the host directly for more information.
Winchester Top Rated Vacation Rentals
House
10.0(73 Reviews)
4 Bedrooms
5 Baths
12 Guests
3039 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R10,815/Night
7 Nights - R75,708
House
10.0(56 Reviews)
3 Bedrooms
2 Baths
8 Guests
2050 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R5,410/Night
7 Nights - R37,878
House
10.0(52 Reviews)
3 Bedrooms
2 Baths
100 Guests
2001 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R6,728/Night
7 Nights - R47,100
House
10.0(32 Reviews)
4 Bedrooms
3 Baths
14 Guests
2500 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R7,843/Night
7 Nights - R54,910
House
10.0(19 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R8,885/Night
7 Nights - R62,200
Apartment
10.0(14 Reviews)
4 Bedrooms
2 Baths
13 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
R5,555/Night
7 Nights - R38,885
House
10.0(11 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R9,738/Night
7 Nights - R68,175
House
10.0(11 Reviews)
4 Bedrooms
3 Baths
12 Guests
26910 ft²
Private Pool- Fireplace/Heating
- Pool
- Kitchen
R7,756/Night
7 Nights - R54,293
