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Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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Superhost
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, 205 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)

Top guest favourite
The cottage exterior features a welcoming red facade with white trim, complemented by a covered porch. A rocking chair is positioned on the porch, adding a cozy touch. Lush green landscaping frames the entrance, providing an inviting approach to the home.
Cottage in Tullahoma
4.98 out of 5 average rating, 125 reviews

Cottage at The Reserve sleeps 10

Perfect family friendly get-away at Tims Ford Lake. The cottage is located on a beautiful, completely wooded lot. You have access to Holiday Landing Marina via a subdivision golf cart path. Whether you want to go boating on the lake, hike at the nearby Tims Ford State Park, or just get together with family and friends, look no further! This large open concept, cozy, spacious, 3-level home is all you will need. Brand new furnishings and mattresses! Our space also includes 5 large 4K ROKU TVs.

Superhost
Home in Winchester
4.81 out of 5 average rating, 140 reviews

Charming Retreat 5 Min to Tims Ford Lake; Sleeps 8

Welcome to your beautifully renovated 1940s historic home in Winchester, Tennessee, just 5 minutes from Tims Ford Lake. This spacious 4-bedroom, 3-bath vacation home comfortably sleeps 8. Guests will appreciate fast Wi-Fi, a Roku Smart TV, and large comfortable bedrooms. Perfect for: • Family vacations and reunions • Boating and fishing trips at Tims Ford Lake • Couples or friends’ weekend getaways • Exploring historic Winchester • Quiet countryside retreats with beautiful sunrises and sunsets

Guest favourite
A close-up view features a stylish light fixture beside a dark, round table. The background showcases a textured wallpaper with bold, black plant motifs. A soft white bed is highlighted, accompanied by a decorative pillow with black and white fringe.
Home in Winchester
5 out of 5 average rating, 20 reviews

Location, location, location!

No detail has been left undone when it comes to cleanliness, decor, or amenities. Tims Ford Boat Launch <1/4 mile, walk to Twin Creeks, Walk to historic Winchester square (< 1mile) where you can enjoy several dining/shopping options. Hike the mountains, tour Sewanee, Jack Daniels or Dickel, boat at Tims Ford, float the Elk, or just relax at this oh so quaint home. The location is also convenient for concerting at The Caverns. If you are tired of boring and unclean rentals, look no further!

Top guest favourite
A screened porch is furnished with a comfortable sofa and chairs, arranged around a sturdy coffee table. A ceiling fan is installed for airflow, and a wall-mounted TV provides entertainment. Large windows allow natural light to fill the space while offering views of the surroundings.
Townhouse in Winchester
5 out of 5 average rating, 34 reviews

Lovin Lake Life

Relax and unwind at this spacious 5BR/7-bed townhome just 1-2 minutes from Twin Creeks Marina & Dry Creek Beach! Take the complimentary golf cart and relax by the pool or head to the marina to rent a boat, shop at the store, or eat/drink at Drafts & Watercrafts Bar & Grill. Enjoy cozy furnishings, relax on the screened in porch, or challenge your group to a game of ping pong. This home is perfect for families, groups, and lake lovers looking for a fun and easy getaway in Winchester, TN.

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, 67 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!

Top guest favourite
A view from the porch reveals the serene waters of Tims Ford Lake, bordered by lush greenery. The railing is partially visible, with sunlight filtering through the trees, creating dappled shadows on the deck. A bird feeder hangs nearby, inviting wildlife.
Cabin in Lynchburg
4.96 out of 5 average rating, 217 reviews

Cozy Cabin on Tims Ford Lake

Come stay at a hand built log cabin nestled right on Tims Ford Lake. Enjoy a cup of coffee and watch birds fly in a rocking chair on the front porch. Relax in the porch swing as you see fish jump from the water. Grill out on the back porch while watching the sun set. There is a dock available for fishing. The cabin is five miles from Tims Ford State Park, eight miles from Jack Daniels Distillery and downtown Lynchburg, eleven miles from Tullahoma, and fifteen miles from Winchester.

Top guest favourite
A modern two-story house features a green exterior with white trim and a welcoming porch. An American flag hangs from the porch, and soft outdoor lighting illuminates the entrance. A driveway leads to a garage, with trees providing a natural backdrop.
Home in Tullahoma
5 out of 5 average rating, 104 reviews

Lakeside Retreat at The Reserve w/ Golf Cart

Beautiful lakeside home on Tim's Ford Lake! Short Walk or Golf Cart ride to Blue Gill Grill & Holiday Landing Marina. Boat Parking on the Driveway during your stay! First Floor: Master Bed with Full Bath, Dining Room, Living Room, Kitchen (Fully stocked with basic spices and cooking utensils). Outside Patio with Fire Place and seating. Second Floor: BR 2- King Bed. BR 3 Queen Bed, Loft Space, Sectional Couch, Pull out Queen. *No Smoking *Max 10 Guest *Front Door Security Cam*

Guest favourite
Cabin in Coalmont
4.98 out of 5 average rating, 358 reviews

The Coalmont Cabin - Romantic Lakefront Escape

The Coalmont is a 4 acre waterfront retreat on top of the South Cumberland Mountains of Tennessee, between Nashville and Chattanooga. This 460 sq ft "tiny" cabin sleeps up to 4. Amenities abound with boats, hot tub, fishing, zip line, lawn games, large decks for gathering, fire pit, and beautiful scenery. Perfect retreat for couples looking for a romantic getaway, families wanting to unplug and reconnect with quality time, or anyone looking for a quiet place to work remotely.

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, 26 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.

Popular amenities for Winchester holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Winchester

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

Guest favourite
A contemporary white house with a stylish facade features a covered entrance. A golf cart is parked on the driveway, adjacent to a well-maintained lawn. Two large windows flank the door, contributing to the home's inviting appearance.
Home in Winchester
5 out of 5 average rating, 17 reviews

Lake House in Winchester, Tn w/Golf Cart

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

Dome in Tracy City
5 out of 5 average rating, 3 reviews

Highland Bluff Dome

Top guest favourite
A bright sunroom with panoramic lake views features large windows allowing natural light to fill the space. A comfortable white sofa is accompanied by two rattan chairs, creating a relaxing atmosphere. A ceiling fan maintains airflow, and light wood flooring enhances the openness.
Home in Winchester
4.97 out of 5 average rating, 72 reviews

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

Guest favourite
A screened-in porch features a cozy seating area with two rattan chairs and a coffee table. A modern fireplace is centrally located, with a television mounted above it. Light enters through large windows, complementing the warm wooden ceiling.
Cottage in Tullahoma
4.94 out of 5 average rating, 87 reviews

Cozy Designer Cottage at the Lake with Hot Tub

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
4.89 out of 5 average rating, 38 reviews

Cottage on Cedar

Top guest favourite
A modern two-story house features a blend of black and white exterior with a spacious driveway and manicured lawn. Balconies adorned with black railings overlook the landscaped yard. A connected garage and an outdoor seating area enhance the inviting atmosphere of this lakeside home.
Home in Winchester
5 out of 5 average rating, 8 reviews

Peaceful Getaway on Kayak Way – Winchester

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price€ 163€ 163€ 165€ 164€ 221€ 268€ 267€ 241€ 184€ 189€ 185€ 156
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 € 26 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

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