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Vacation rentals in Winchester

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Quick stats about vacation rentals in Winchester

  • Total vacation rentals

    Explore 130 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at G$2,088 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,020 verified reviews to help you choose

  • Family-friendly vacation rentals

    130 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Winchester vacation rentals include wi-fi 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!

Top-rated vacation rentals in Winchester

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

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Guest favorite
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.
Apartment in Winchester
4.89 out of 5 average rating, 82 reviews

Winchester's Premier Downtown Loft! Near The Lake!

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!

Top guest favorite
A spacious covered dock extends over the tranquil waters, featuring two large swings for relaxation. Kayaks are positioned nearby, surrounded by lush greenery. Steps lead up from the dock to the home situated among the trees, creating a serene lakeside setting.
Home in Winchester
5 out of 5 average rating, 26 reviews

Lakeside Serenity: Cove Retreat

Escape to the heart of Tims Ford Lake with this beautifully remodeled lakefront home boasting a full-glass sunroom and a private dock situated in a peaceful wide cove, providing an unparalleled setting for swimming, boating, and fishing. The seclusion created by its location in a cove has the same advantages of a neighborhood cul-de-sac. What sets our home apart is the tranquility provided by a lack of passing boat traffic, a ‘cabin in the woods’ feel, and its proximity to area attractions.

Guest favorite
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, 23 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!

Guest favorite
A modern two-story home features clean lines and a light-colored exterior. Large windows are present on the upper level, complemented by a stylish black garage door. Minimal landscaping includes a small tree near the front entrance, and a paved driveway offers access to the home.
Home in Winchester
4.81 out of 5 average rating, 27 reviews

Dry Jack Tim-Hot Tub, Water Views, Marina

Escape to this beautiful lake home in the sought-after Twin Creeks community on Tims Ford Lake! Enjoy water views, a relaxing hot tub, complimentary golf cart, and community pool just steps away. Bring your boat and launch from Twin Creeks Marina or rent pontoons, kayaks, and paddleboards onsite. Grab drinks, snacks, and fuel at the marina store, then unwind with lakeside dining and live weekend music at Drafts & Watercrafts Bar and Grill at the Marina. Also, 5 min from downtown Winchester.

Top guest favorite
Home in Winchester
5 out of 5 average rating, 60 reviews

The Hangout on Heath Lane

Welcome to The Hangout on Heath Lane! Just 1/2 mile from Twin Creeks Marina and 1 mile from historic downtown Winchester, our new 2-bedroom retreat is the perfect home base for lake weekends, concerts at The Caverns, Jack Daniel's tours, and family getaways. Enjoy modern comforts, sparkling cleanliness, and the small-town charm that keeps guest coming back! We also suggest: -Coffee & breakfast or lunch at Walnut Hill Coffee Shop -For a delicious, upscale dinner, go visit Filo's Tavern

Guest favorite
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, 128 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 favorite
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
4.98 out of 5 average rating, 80 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 favorite
The kitchen features modern stainless steel appliances, including an oven and microwave, set against green cabinets. A spacious granite countertop with a farmhouse sink is complemented by decorative floating shelves displaying dishware and plants, while a patterned backsplash adds visual interest.
Home in Winchester
4.86 out of 5 average rating, 51 reviews

1940 Renovated Cottage Near Square/Lake Summer Fun

WELCOME to this beautiful, newly renovated COTTAGE near the Winchester Square and Tim's Ford Lake. This Historic Home, built in 1948 is full of CHARACTER but yet modern and stylishly furnished. Within walking distance to the Winchester Square and just 1 mile from Twin Creeks Marina this beautiful home is convenient, comfortable, and welcoming for all guests. This is the home that you have been looking for that is BUDGET friendly but also packed with AMENITIES in the perfect location!

Top guest favorite
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, 43 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.

Guest favorite
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.
Apartment in Winchester
4.97 out of 5 average rating, 31 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 favorite
Home in Winchester
5 out of 5 average rating, 21 reviews

Lakeside Manor Retreat

Enjoy your stay at this gorgeous modern style sanctuary, nestled on 2 acres near Tim’s Ford Lake. A private oasis, only 2 blocks from Twin Creeks Community & 6 blocks from Historic Downtown. Featuring gorgeous kitchen w/bar, wine fridge, ice machine, granite islands ,2 master suits with XL soaking tubs, 4 bedrooms, 3.5 baths, 7 TVs, air hockey & more! Sleeps 12. Plenty of parking. Message us with any questions. Thank you for your interest in Lakeside Manor.

Top guest favorite
The exterior view showcases a Craftsman-style house bordered by a spacious deck. A wooden pergola arches over part of the deck, enhancing the outdoor living space. The yard features manicured grass and is enclosed by a black fence for added privacy.
Home in Winchester
4.93 out of 5 average rating, 138 reviews

Lovely Lake View Home at Twin Creeks Marina

This Craftsman-style, lake-view house is located in the private, gated lakeside community of Twin Creeks Village at scenic Tim's Ford Lake in Winchester, TN. It features an open floor plan with 4 bedrooms, 3 baths, game room, screened porch and huge deck overlooking the lake. Use the included golf cart to go to the swimming pools, marina, bar & grill or on-site convenience store. Information on boat & jet ski rentals are available at the marina shop.

Popular amenities for Winchester vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Winchester

Guest favorite
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
4.87 out of 5 average rating, 39 reviews

Luxury 3BR lakeside escape

Superhost
The entryway features a welcoming porch with two comfortable seating areas, one composed of wooden rocking chairs and another wicker chair. A decorative welcome mat greets guests, while a handcrafted wreath adorns the door, inviting all into the cozy interior beyond.
Home in Winchester
4.76 out of 5 average rating, 25 reviews

Lakeside Luxe | Lake + Pool Access

Guest favorite
Vacation home in Winchester
5 out of 5 average rating, 7 reviews

HideAway @ Tim's Ford Lake 4BR/3BA - Private Dock

Home in Winchester
4.81 out of 5 average rating, 144 reviews

Charming Retreat 5 Min to Tims Ford Lake; Sleeps 8

Top guest favorite
Home in Winchester
4.97 out of 5 average rating, 79 reviews

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

Home in Winchester
5 out of 5 average rating, 4 reviews

4-bedroom Lake house in Twin Creeks Winchester TN

Top guest favorite
Guesthouse in Tullahoma
5 out of 5 average rating, 13 reviews

Tennessee Barrel House

Guest favorite
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
4.91 out of 5 average rating, 47 reviews

Cottage on Cedar

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$37,174 GYDG$33,624 GYDG$39,053 GYDG$39,680 GYDG$53,464 GYDG$64,741 GYDG$64,532 GYDG$58,267 GYDG$44,483 GYDG$45,736 GYDG$44,692 GYDG$37,592 GYD
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.

Destinations to explore

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