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Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favourite
Apartment in Winchester
4.91 out of 5 average rating, 53 reviews

Unbeatable Charm & Convenience On The Square!

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!

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)

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

Top guest favourite
The exterior of a modern two-story home is displayed, featuring a light-colored facade with black accents. A garage door complements the structure, while a decorative blue door offers an inviting entrance. The manicured lawn extends towards the serene lake visible in the background.
Home in Winchester
5 out of 5 average rating, 47 reviews

Lakefront Haven | Hot Tub | Kayaks, Firepit

Welcome to Lakefront Haven! This home offers a seamless blend of comfort and luxury, providing a retreat for a lakefront getaway. • Lakefront property + beautiful views • Hot Tub • Fantastic community pool for the hot summer days • Screened in, heated porch with TV and sound system • Kayak, 2 Paddleboards and Peleton provided • Deck with gas Weber grill • Backyard firepit with chairs • Well equipped kitchen • Less than two miles from Twin Creeks Marina • Walkable to the downtown Square

Top 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 homes in Winchester
4.99 out of 5 average rating, 74 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.

Guest favourite
A spacious living area features a large sectional sofa with cozy throw blankets placed upon it. Tall windows provide natural light and views of the surrounding trees. A wooden dining table is visible in the background, accommodating multiple guests.
Home in Winchester
4.93 out of 5 average rating, 59 reviews

Tim’s Ford Lake 6BR private dock near Twin Creeks

A little piece of Heaven on Tims Ford Lake! Our waterfront home is a 5,000 sqft woodsy retreat with beautiful views. Close to Twin Creeks Marina. Beautiful vaulted ceiling’s and floor to celing windows. This house can accommodate several families, with 6 bedrooms and a spacious basement game room that truly has it all! Large covered patio, two decks off the main level overlooking the lake with cozy seating and spectacular views. Large covered dock with one slip, kayak launch, and sun deck.

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!

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 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*

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.
Apartment in Winchester
4.96 out of 5 average rating, 27 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 vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation 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

Top guest favourite
A fire pit made of stone is situated by the water, surrounded by two outdoor chairs. The view reveals a serene lake bordered by lush greenery under a bright blue sky with soft clouds.
Home in Winchester
5 out of 5 average rating, 31 reviews

Barefoot Bliss w/Stunning Waterfront Lot & Pool

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

Guest favourite
The exterior of the historic home is shown, featuring a large front yard with manicured grass and a stone pathway leading to the entrance. The two-story structure has a gray metal roof and a charming porch with chairs, framed by trees against a twilight sky.
Home in Winchester
5 out of 5 average rating, 21 reviews

Sweet Retreat-across from Twin Creeks Marina

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

A three-level home is set against a backdrop of greenery, featuring a spacious deck with outdoor seating. Large windows illuminate the brick facade, which is complemented by blue planters. The surrounding lawn is well-kept, enhancing the inviting exterior of this peaceful retreat.
Townhouse in Winchester
4.74 out of 5 average rating, 23 reviews

Lakeview Luxe Life 2 decks with views & Large dock

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.
Apartment in Winchester
4.87 out of 5 average rating, 68 reviews

Winchester's Premier Downtown Loft!

When is the best time to visit Winchester?

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Avg. price$262 CAD$260 CAD$265 CAD$263 CAD$355 CAD$429 CAD$428 CAD$387 CAD$295 CAD$303 CAD$296 CAD$249 CAD
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 vacation rentals in Winchester

  • Total vacation rentals

    Explore 130 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at $42 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,850 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space and 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

  • Wifi availability

    120 of Winchester vacation 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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  5. Winchester