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Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A charming two-story house features a blue and white exterior with a welcoming front porch. Two wooden rocking chairs sit invitingly on the porch. Lush greenery surrounds the property, complemented by a broad driveway leading up to the entrance.
Home in Tullahoma
5 out of 5 average rating, 8 reviews

Tennessee Whiskey -Cozy Screened Porch + Fireplace

Peaceful lake retreat with marina access and a screened porch featuring a gas fireplace. 3 comfy bedrooms, 2.5 baths, a well equipped kitchen, movie room with 75" TV, & thoughtful touches make it ideal for families, couples, or small groups. Quiet, cozy, & made for making memories ,Tennessee Whiskey is your escape-from-it-all home away from home. We are a short drive to the iconic distilleries of Jack Daniels, Nearest Green, and George Dickle. Book your stay & experience the perfect getaway!

Guest favourite
A spacious living area features two black leather sofas facing each other, inviting relaxation. A decorative coffee table sits in the center on a patterned rug. Exposed brick walls and large windows provide ample natural light, while modern lighting fixtures enhance the room's ambiance.
Flat in Winchester
4.86 out of 5 average rating, 66 reviews

Winchester's Premier Downtown Loft!

Escape to The Heritage Lofts, just off of the thriving Winchester square. Only minutes from Tims Ford Lake, this fabulously-renovated apartment has all of the comfort and amenities you need to feel right at home during your stay in Winchester. See the local scene in style with one of our bike or paddle board rentals, and shop til you drop on our thriving downtown square. Then grab a meal before relaxing in the comfortable confines of your spacious loft. There isn't a better spot to stay in town!

Guest favourite
A comfortable living area is observed, featuring a light-colored sectional sofa and a dark wooden coffee table. Large windows provide natural light, while a rustic dining table and chairs are visible in the background. Decorative wall art and assorted accents highlight the cozy atmosphere.
Cabin in Winchester
4.85 out of 5 average rating, 204 reviews

Private Dock - Best Cabin Tims Ford Lake

Great cabin located directly on Tims Ford Lake. Cabin has been updated and includes nice, well stocked kitchen as well as a deck (with grill). Enjoy our dock - fish, swim and use our two kayaks, paddle board and a canoe. Plenty of space to tie your boat up to our dock in a mostly private cove. Please read the guest access section for more details on lake access. Close to some great attractions - Jack Daniels Distillery (19 mi), Bonnaroo (25 mi), Univ. of the South (19 mi), Winchester (5 mi)

Guest favourite
A modern tiny home is surrounded by open grass fields, featuring a welcoming porch with wooden steps. Large windows provide natural light, while the exterior showcases a black siding and a gable roof. A gravel path leads to the entrance, enhancing accessibility.
Tiny home in Winchester
4.99 out of 5 average rating, 73 reviews

Tiny House

You will feel right at home in this adorable Tiny Home with RV Hookups! This picture-perfect little cottage has a bedroom with queen size bed, full bath with tile walk-in shower, full kitchen with all of the amenities, and living room with queen size sleeper sofa. The back porch offers peace, quiet, and spectacular mountain views. This property is super convenient to Tims Ford Lake, The Caverns music venue, Jack Daniels Distillery, University of the South, and historic downtown Winchester.

Top guest favourite
A welcoming porch area features vibrant red flooring, complemented by a metal table and chairs. A vintage mailbox stands prominently, while a grill and a chiminea add to the rustic charm. Potted plants are placed nearby, enhancing the outdoor living space.
Cabin in Estill Springs
4.94 out of 5 average rating, 281 reviews

Holliday Hide Away

1200 sq. ft. very rustic converted pole barn. The floors are stained concrete and the walls are rough saw mill hewn poplar boards. Located on 3 acres of beautiful well kept property. It does not border the lake but is surrounded by Tims Ford Lake and less than 5 minute drive to 3 boat docks and launches. Close to restaurants, shopping venues, hiking trails, water falls and golfing. Pool table, cornhole set, board games & cards in cabin. Visit historic Franklin County and surrounding areas.

Top guest favourite
A covered porch features comfortable seating arrangements, with two cushioned chairs positioned around a circular wooden table. A spacious grassy yard extends beyond the porch, framed by lush greenery and trees. The tranquil waters of Tims Ford Lake can be glimpsed in the background.
Home in Winchester
5 out of 5 average rating, 22 reviews

Sunset Cottage +Dock on Tims Ford Sleeps 12

Welcome to Sunset Cottage, a spacious and serene lakeside escape nestled in the heart of Winchester. Located less than a mile from the town square, this charming cottage offers both the tranquility of lakefront living and the convenience of nearby dining and shopping. Relax as you take in breathtaking sunset views from the back covered porch. With a private boat dock, you can easily set out for a day on the water. Designed for comfort and relaxation, Sunset Cottage is the ideal getaway.

Guest favourite
An outdoor seating area features blue and white lounge chairs arranged around a central fire pit. The shaded porch swing offers a serene view of the lake, framed by lush greenery. The dock and numerous boats can be seen in the background.
Home in Winchester
4.96 out of 5 average rating, 123 reviews

Private dock/gazebo on quiet cove. Tims Ford Lake!

Indulge in the tranquility of Tims Ford Lake, TN! Our exquisite 5-star cottage, just 6 miles from Tims Ford State Park/Marina, beckons you to unwind. Conveniently situated 18 miles from Tullahoma and 8 miles from Winchester, our boat-friendly haven features a private dock and a circular drive. Minimum rental age: 25. Ensure a seamless stay by signing our legal Rental Agreement and presenting a government-issued ID. Book now for a worry-free lakeside escape – your perfect retreat awaits!

Top guest favourite
A modern guesthouse is set against a backdrop of lush greenery and a serene pond. The building features dark siding with wooden accents, while a well-maintained lawn leads to a gravel path. Bright blue skies and scattered clouds provide a peaceful atmosphere.
Home in Winchester
4.97 out of 5 average rating, 64 reviews

Meadow View Retreat

Enjoy your stay at Meadow View Retreat with a beautiful view of the farm. We have a 72 acre farm and a family business located walking distance from the airbnb. We are a 10 minute drive to Tim’s Ford Lake, Twin Creeks Marina & historic downtown Winchester + 15 minutes from University of the South. This 2 bedroom guesthouse is the perfect stay for you and your loved ones. Enjoy the private, quiet back porch with a view of the pond and the farm. Beautiful sunrise + sunset views too!

Guest favourite
A wooden dock extends over the tranquil water, featuring kayaks and paddleboards secured alongside. An upper deck with several chairs offers a relaxing space, while views of the lush surroundings create a calming atmosphere. The water sparkles under clear blue skies.
Home in Winchester
4.98 out of 5 average rating, 108 reviews

Lake Home, Dock, Theatre, Hot Tub, FirePit, Kayaks

Take it easy at this unique and tranquil getaway. This beautiful lake home is one of it's kind at Tim's Ford. The house is nestled in a quiet rural neighborhood with woods in the backyard. The dock is only a small golf cart ride away. Enjoy beautiful lake views at your own private dock! This house is equipped with an amazing home theatre system, game room, hot tub, fire pit, kayaks and plenty more amenities! Tim's Ford Dam is only one mile away and has a public boat launch for you :)

Top guest favourite
A contemporary two-story home showcases a light-colored exterior with a gabled roof and a covered front porch. A balcony extends from the upper level, complemented by a ceiling fan. The landscaped area features low shrubbery and a paved pathway leading to the entrance.
Home in Winchester
5 out of 5 average rating, 37 reviews

The Modern Mainstay at Barefoot Bay

Welcome to The Modern Mainstay, your stylish retreat by the shores of Tims Ford Lake! This pet friendly contemporary home is just 1/2 mile from the historic downtown square where you can enjoy doing a bit of shopping or dining. Or sit on the front porch with lake views, and take in the serene surroundings. Take a dip in our lakefront community pool. Enjoy access to the lakefront common area for fishing, swimming in the lake, and relaxing by the fire pit with a glass of wine.

Top guest favourite
A modern kitchen area features light wooden cabinets and stainless steel appliances. A round dining table with black chairs is set with a decorative centerpiece. Natural light filters through a window, enhancing the neutral color palette of the space.
Flat in Winchester
4.96 out of 5 average rating, 24 reviews

Clean Lines and Simple Comfort

This 2 bed, 2 bath apartment duplex is located just two miles from Tims Ford Lake. Whether you’re in town for a weekend or an extended stay, this space offers everything you need for a relaxing and comfortable visit. Each room features a comfortable queen bed, fresh linens and ample closet space. The kitchen is stocked with cookware, stainless steel appliances, and a coffee maker for your morning brew. Book your stay and enjoy an experience that’s clean with a blend of style.

Top guest favourite
A modern structure features a sleek black exterior with wooden shutters. A covered porch is highlighted by two chairs and a potted plant, inviting relaxation. Lush greenery surrounds the home, providing a serene outdoor environment.
Home in Winchester
5 out of 5 average rating, 45 reviews

The Hangout on Heath Lane

Enjoy a peaceful experience at this centrally-located home. The Hangout is half a mile from the beautiful Twin Creeks Marina and 1 mile to historic downtown Winchester! Other local attractions include: -Grab a coffee and enjoy a tasty breakfast or lunch at Walnut Hill Coffee Shop -For a delicious, upscale dinner, be sure to visit Filo's Tavern -Head out for a tour and tasting at Jack Daniels Distillery -Grab some tickets to the Cavern's for a memorable concert experience.

Popular amenities for Winchester holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Winchester

Guest favourite
A modern house exterior is depicted, featuring a gable roof and a mix of vertical and horizontal siding. Black window frames and decorative wood accents provide contrast against the light-colored façade. A paved driveway leads to a single-car garage, with a white vehicle parked nearby.
Home in Winchester
4.88 out of 5 average rating, 34 reviews

Luxury 3BR lakeside escape

Top guest favourite
The exterior of a two-story house is displayed, featuring a covered balcony with ceiling fans and outdoor seating. The structure is painted in a deep blue, complemented by white trim. A stone veneer base supports the house, and a well-maintained lawn extends in front.
Home in Winchester
5 out of 5 average rating, 31 reviews

Hydrotherapy Haven

Top guest favourite
Home in Winchester
5 out of 5 average rating, 12 reviews

Lakeside Manor Retreat

Top guest favourite
An inviting living room features contemporary furnishings, including a plush sectional sofa accented with decorative pillows. A light fixture hangs from the ceiling, and large windows allow natural light to brighten the space. A door leads to the outdoor area, enhancing accessibility.
Home in Estill Springs
5 out of 5 average rating, 28 reviews

Tailored for Tranquility

Guest favourite
The front entrance of the cottage features a welcoming green door framed by white siding and a covered porch. A potted plant adds a touch of greenery beside the entrance, and a stone pathway leads to the door, inviting guests inside.
Home in Winchester
4.95 out of 5 average rating, 37 reviews

Cottage on Cedar

A two-story home showcases warm exterior tones with light blue shutters and a welcoming front porch. Soft sunset colors illuminate the sky, while a paved driveway leads to a one-car garage, bordered by manicured landscaping and trees in the background.
Home in Winchester
4.85 out of 5 average rating, 47 reviews

Gorgeous lake home in Twin Creeks with Lake View

A functional kitchen features teal cabinetry and a black stove. A wooden bowl sits at the center of a dark table adorned with a floral yellow tablecloth. Wall art and decorative tiles add character, while natural light brightens the workspace.
Flat in Winchester
4.83 out of 5 average rating, 58 reviews

Just Around the Corner

A spacious two-story brick house is framed by green lawns and neatly trimmed bushes. Large windows with black shutters line the front, and a covered entrance is visible on the left. A clear blue sky serves as the backdrop, enhancing the home's inviting presence.
Home in Winchester
4.88 out of 5 average rating, 8 reviews

The Perfect Getaway

When is the best time to visit Winchester?

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Avg. price£143£142£145£144£194£235£234£211£161£166£162£136
Avg. temp5°C8°C12°C17°C21°C25°C27°C27°C23°C17°C11°C7°C

Frequently Asked Questions

  • What are the best places to stay in Winchester?

    Vacation rentals around Winchester’s downtown neighborhoods and near the lakeside provide relaxed settings. Areas close to parks, shops, and community spaces are frequently favored by visitors.

  • What are the best things to do in Winchester with kids?

    Kids can explore playgrounds, enjoy lakeside parks, and participate in fishing or boating. Attending seasonal events and visiting small museums around the town square is also popular with families.

  • What are some of the best things to do in Winchester?

    Explore the historic town square, enjoy water activities at area lakes, and visit small museums or local shops. Outdoor recreation, seasonal festivals, and community gatherings are frequently suggested.

  • How is the weather in Winchester?

    Winchester has cooler winters around 32–51°F (0–11°C), and warmer summers near 71–91°F (22–33°C), with rainfall throughout the year. Spring and fall bring comfortable temperatures and are popular seasons for outdoor activities.

  • When is the best time to visit Winchester?

    Late spring and early fall are often recommended, with milder temperatures between 50–84°F (10–29°C) and less rainfall. Summer draws visitors for outdoor recreation and community festivals near the lake.

  • What are the best places to visit in Winchester?

    Explore Winchester’s historic town square, lakeside parks, and small museums that share local heritage. Antique shops and public green spaces frequently attract visitors year-round.

  • What are some hiking trails in Winchester?

    Winchester has easy nature walks and longer trails around local parks and the lake area. Trailheads frequently include shaded paths, water views, and spaces for birdwatching.

  • What are some family activities we can do in Winchester?

    Families can enjoy lakeside parks, fishing, playgrounds, and small museums around Winchester. Seasonal events on the town square and water activities at area lakes are often favorite outings.

  • What are some of the best day trip ideas from Winchester?

    Consider exploring natural areas, state parks, or neighboring small towns with distinct local culture and shops. Regional wineries, historic sites, and hiking trails are frequently suggested for day outings.

  • Are there any pet friendly accommodations available in Winchester?

    Winchester has pet friendly vacation rentals in neighborhoods near parks and the lake. Some hosts also provide outdoor spaces or walking trails for guests traveling with pets.

  • What are some local tips for visiting Winchester?

    Locals suggest exploring both downtown shops and the lake area, especially for outdoor recreation. Arrive early for community events, and enjoy regional foods at neighborhood diners for an authentic experience.

  • What is Winchester known for?

    Winchester is known for its historic town square, nearby lakes, and regional traditions rooted in Southern culture. The area often draws visitors for fishing, boating, and community celebrations.

  • What are the best hidden gems to explore in Winchester?

    Explore local antique shops, small-town museums, and quiet nature trails around Winchester. Some visitors discover riverside parks and scenic spots just outside the main town area.

  • What are the best foods to try in Winchester?

    Winchester has locally rooted Southern dishes, including barbecue, fried catfish, and seasonal produce. Bakeries and cafes frequently suggest homemade pies and country breakfasts as regional specialties.

  • What should I bring for a trip to Winchester?

    Pack comfortable clothing suitable for outdoor activities, as local weather varies from 32–91°F (0–33°C) through the year. Include sturdy shoes for hiking, sun protection, and light rain gear, especially in spring and summer.

  • What is the nightlife in Winchester like?

    Winchester’s nightlife centers around casual gathering spots, including locally run cafes, laid-back bars, and venues with live music. Social evenings often take place near the town square or around lakeside restaurants.

  • What are the most popular events or festivals in Winchester?

    Winchester frequently hosts community fairs, seasonal festivals, and locally rooted celebrations around the town square. Summer often features events near public parks and lakefront areas, drawing both residents and visitors.

  • Are there family friendly vacation rentals in Winchester?

    Winchester has a selection of vacation rentals that welcome families, with some homes featuring spacious layouts, yards, and access to nearby parks. Look for stays around peaceful neighborhoods or near recreational lakes.

Quick stats about holiday rentals in Winchester

  • Total holiday rentals

    Explore 130 holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at £23 per night before taxes and fees

  • Verified guest reviews

    Over 3,850 verified reviews to help you choose

  • Family-friendly holiday rentals

    120 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    120 of Winchester holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winchester rentals

  • 4.9 Average rating

    Winchester stays are highly rated by guests – averaging 4.9 out of 5!

Destinations to explore

  1. Airbnb
  2. United States
  3. Tennessee
  4. Franklin County
  5. Winchester