Home Vacation Rentals By Owner In Winchester, TN

Showing 40 Of 149 Vacation Rentals
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Exceptional(53)

$405.79

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Private Vacation Home

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

Winchester, Tennessee, United States

Your dream lakefront getaway begins at this 3-bedroom, 2.5-bath vacation rental situated in the gated community of Barefoot Bay. Featuring a modern interior with picturesque lake views from almost every room and an outdoor oasis complete with a furnished patio and a flat lot with direct lake access right from the backyard this luxurious home will suit all your needs. Rent a boat or stay for a bite and live entertainment at Twin Creeks Marina or shop for souvenirs in downtown historic Winchester.brbr-- THE PROPERTY --brbrFour-Season Sunroom | Situated Directly on Tims Ford Lake | Furnished Patio | Modern Decor | Community Pool (Open Now)brbrBring your family of lake lovers to this stunning waterfront retreat, brimming with entertainment, direct lake access, and all the modern comforts of home as well as close proximity to the area's best lake amenities, downtown Winchester, and outdoor recreation.brbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Queen Beds | Additional Sleeping: Air Mattress, Twin Rollaway BedbrbrCOMMUNITY AMENITIES: Kayak/jet ski ramp, clubhouse, outdoor seasonal poolbrOUTDOOR LIVING: Patio w/ Adirondack chairs, gas grill, side porch w/ 3 piece bistro set, large yard, kayak launch, portable fire pit, swimming floats, solo stove fire pit, swimming floats, beach towelsbrINDOOR LIVING: 5 Smart TVs w/ 125+ cable channels, gas fireplace, dining table, furnished sunroom, interior lake views, open floor plan, large bedroom closets, Amazon Alexa'sbrKITCHEN: Fully equipped, stainless steel appliances, dishwasher, microwave, Keurig + drip coffee maker combo, coffee + tea provided, toaster, crockpot, dishware/flatware, breakfast bar w/ seating, paper goodbrGENERAL: Free high-speed Xfinity WiFi (200 Mbps), washer/dryer, laundry detergent, linens/towels, A/C, complimentary toiletries, ceiling fans, beach towels, WiFi thermostats, central A/C & heating, keyless entry, cards/gamesbrSUITABILITY: Bedrooms + full baths on 2nd floor, use caution with young children (no fence, directly on lake)brFAQ: Quiet hours (10:00 PM - 7:00 AM), Ring doorbell + exterior security camerabrPARKING: Driveway (3 vehicles max), trailer parking allowed (owner approval needed)brbr-- THE LOCATION --brbrTIMS FORD LAKE (on-site): Swimming, boating, fishing, water sports, kayaking, Winchester City Park public boat ramp (0.9 miles), Dry Creek Beach (1.8 miles), Twin Creeks Marina - boat/kayak/paddle board + boat slip rentals, live entertainment + concerts, Drafts & Watercrafts restaurant (2.0 miles), Tim's Ford Lake Devil's Step Boat Launch (4.8 miles), Tims Ford State Park (11.1 miles)brHISTORIC WINCHESTER (~1 mile): Restaurants, distilleries, specialty gift shops, museums, garden, The Oldham movie theater, festivalsbrGOLF: Scenic View Golf Course (7.5 miles), Jack Nicklaus Bear Trace At Tims Ford State Park (11.9 miles), The Course at Sewanee (15.0 miles)brAIRPORT: Nashville International Airport (83.6 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- The maximum occupancy of 8 guests is strictly enforced at all timesbr- Please observe quiet hours from 10:00 PM - 7:00 AMbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Please use caution with children as this property is directly on the lake with no fencebr- NOTE: All bedrooms and full bathrooms are located on the 2nd floor and require stairs. This property might not be suitable for guests with limited mobility br- NOTE: If you plan to bring a trailer with you for boats and jet skis, please let the owner know after booking so they can approve, as there is limited parking space on-sitebr- NOTE: Your safety matters. There is a Ring doorbell security camera, located next to the front door facing out and an exterior camera located on the backside of the house facing out. They do not look into any interior spacesbr- NOTE: Grilling is only permitted on the back patio; guests may not grill anywhere else on-sitebr- NOTE: Pool is seasonal, opening and closing dates are determined by the HOA and may vary; for the 2026 season, the pool is scheduled to open on May 15, 2026.
Bed 3

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Bath 2

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Sleep 100

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Exceptional(14)

$475.61

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Private Vacation Home

Breathtaking Lake Views w/Mesmerizing Sunsets

Winchester, Tennessee, United States

Welcome to Sunset Shores! Nestled on the shores of the beautiful Tims Ford Lake, your retreat offers breathtaking views and unforgettable sunsets. Enjoy morning coffee on the deck, water adventures, and cozy evenings by the fire pit. With modern amenities and a serene atmosphere, this is your perfect escape from the everyday hustle. Store your boat and jet skis in the covered slips. Experience nature’s beauty and create lasting memories at your lakeside paradise.brbrThe garage is not available for guest use.brbrAll bedrooms have a beautiful view of the lake and the master has a walk out to the balcony. The property includes a private dock with a slip, ideal for boating enthusiasts. Explore the lake with our provided kayaks, or unwind by the fire pit as you watch the beautiful sunsets. Inside, you`ll find fun for all ages with a pacman arcade game, digital pinball machine, and cozy bunk beds for the kids. This is your perfect escape for relaxation and adventure.brbr-Only 7 min to Tims Ford Marina and Tims Ford State Parkbr-Take a tour at nearby Jack Daniels, Uncle Nearest, or George Dickel distilleriesbr-Home has year around water, but note that water levels will drop November-Mid March and the gangway may be at an incline during that time. The dock is accessible throughout the year. brbrThere are 3 bathrooms with 2 showers in the home, 1 bathroom off one of the downtairs bedrooms has a tub only in it. brbrGuests have full access to the entire lake house and its amenities. Enjoy the spacious deck, private dock, fire pit, and kayaks. The fully equipped kitchen, cozy living area, and all bedrooms are yours to use. You can fit 5-6 vehicles in the driveway and you`ll have Wi-Fi throughout the home. Make yourself at home and take full advantage of this peaceful lakeside retreat.brbrThis home is in a quiet neighborhood with neighbors on both sides. Please follow all speed limit signs as posted. brbr-The property has steps going down to the dock, approximately 60 steps. br-The fireplace in the living room is not functionalbr-There is also a steep dropoff at the edge of the backyard so children should be supervised at all times. br-Must be 25yrs or older to book the propertybr-No Petsbr-No partiesbr-Please be mindful of noise so you do not disturb neighborsbrNo PartiesbrNo PetsbrNo Smoking in the homebrMust be 25yrs of age or older to book the property
Bed 3

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Bath 3

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Sleep 14

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Exceptional(53)

$460.67

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Private Vacation Home

New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

Winchester, Tennessee, United States

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 :). The home theatre is an amazing home theatre projector, not a theatre room. brbrThis is a beautiful quiet neighborhood in rural Winchester that is located on the lake!brbrGolf Cart Is not available to rent December-February. Golf cart is an additional fee of $89 per night if you would like to use it. brbrProperty has seasonal water. TVA will begin reducing water levels in November and will return to normal levels in Mid-March. During this time the dock will not be accessible with a boat.brbrThis home is not a good fit if you are expecting to do a lot of partying. Our home is in a very quiet rural neighborhood that allows short term rentals but we want to respect our neighbors and our home. Also, a new luxury 6 person golf cart is available for rental to make going back and forth to the dock easy and fun! Our dock is toward the top of a cove so you get beautiful views of the main channel but you can also tie your boat off here since there is not much wake.brThis beautiful lake home is in a very nice, quiet, and rural neighborhood so please be respectful to our neighbors and keep the noise down while outside especially after 10:00 or so. :) Also, 4 TOTAL vehicles are allowed in the driveway/garage. Please do not park in the grass or the road. Also, only one vehicle is allowed to parked at the cull de sac where the dock is located. With the lake, dock, stairs and hot tub, clearly, young children MUST BE CLOSELY SUPERVISED AT ALL TIMES for their safety. We have a very friendly neighborhood with an active neighborhood watch. The HOA welcomes renters but bylaws do encourage them to notify owners of inappropriate behavior. Must be 25yrs of age to book the property
Bed 4

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Bath 2

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Sleep 14

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Exceptional(88)

$394.17

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Private Vacation Home

Beautiful Lake Townhouse at Twin Creeks Resort

Winchester, Tennessee, United States

This 4-bedroom townhouse is new and located at the wonderful Twin Creeks Village. This rental offers a golf cart to carry you around the private gated community to the brand-new Marina or one of the swimming pools. The upscale kitchen is fully equipped and complemented by a stainless Saber infrared grill. brbrDownstairs master bedroom has a King-sized bed, 55” tv, and private bathroom. Downstairs also has a spacious family room, screened porch, outdoor patio, bedroom with a 2 Twin trundle, and full bathroom. Upstairs has 2 bedrooms and a full bathroom, one bedroom has King-sized bed and the other boasts of 2 Queen-sized beds, a Full-size trundle, and a pull-out sofa bed. brbrTwin Creeks Village offers three community pools, clubhouse, private event space, Tims Ford Lake’s newest restaurant and marina. The new Twin Creeks Marina and Resort has a floating Ship Store stocked with basic amenities for enjoying one the most scenic lakes in Tennessee, Tims Ford Lake. Also found at the Marina is a public bar and eatery, Drafts & Watercrafts; this on the water restaurant and marina offer lake-flare food, boat rental, spectacular views, and more. The townhome is also within walking distance to the Dry Creek Public Beach. brbrLocated nearby is Bear Trace championship golf course designed by Jack Nicklaus and the University of the south has a pristine 9-hole facility with truly spectacular views. Also, the Jack Daniels Distillery, Monteagle Mountain, and historic downtown Winchester, TN are all just minutes away.
Bed 4

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Bath 3

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Sleep 12

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Exceptional(5)

$418.58

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Private Vacation Home

Lakefront Haven on Tims Ford – Hot Tub, Firepit, Screened Porch & Kayak

Winchester, Tennessee, United States

Welcome to Lakefront Haven! This home offers a seamless blend of comfort and luxury, providing a retreat for a lakefront getaway. brbr• Lakefront property + beautiful viewsbr• Hot Tubbr• Fantastic community pool for the hot summer daysbr• Screened in, heated porch with TV and sound system br• Kayak, 2 Paddleboards and Peleton providedbr• Deck with gas Weber grill br• Backyard firepit with chairs br• Well equipped kitchenbr• Less than two miles from Twin Creeks Marinabr• Walkable to the downtown SquarebrbrFirst Floor:br• Inviting open concept living area with a cozy fireplace and Smart TV + free WiFibr•FULLY EQUIPED KITCHEN and dining area boasting breathtaking lake viewsbr•Powder bathroombr•SCREENED IN PORCH: Glass doors to open up to the screened in porchbr•LAUNDRY ROOM with washer and dryerbr•Dining table for 10 and additional seating available with counter height bar stoolsbrbrUpstairs:br•4 bedrooms and 3 full bathroomsbr•Luxurious master suite with a spa-like bathroombr•Charming queen BUNK ROOM and two additional bedrooms with plush queen bedsbrbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Murphy Bed | Bedroom 4: Queen bunk bed + double Futon brbrAMENITIES: brbr•HOT TUB: 7 seats & lakefront br•PADDLEBOARD & KAYAK: Two stand-up paddleboards and one kayak with SUP accessories providedbr•SPA OPTIONS: We partner with Mountain Mobile Events who will bring the spa day to you! If this is of interest to you, we can send a discount code for you to book your treatment with them. br•KITCHEN: A fully stocked kitchen for culinary adventuresbr•WEBER GRILL: Grill for lakeside BBQsbr•GAMES: Variety of family gamesbr•PELETON and weights br•COMMUNITY POOL & clubhouse open late spring-early fallbr•WALKING DISTANCE to Winchester downtown square—savor meals at Filo’s or grab coffee at Walnut Hill Coffeebr•Just 2 miles from Twin Creeks Marina & Resort for thrilling boat rentals, fishing, tubing, and skiing adventuresbrbrFALL EVENTS: br•Grandaddy’s Farm (Estill Springs, TN) – ~6 miles (about 10 minutes)br•Cove Creek Pumpkin Patch (Monteagle, TN) – ~16 miles (about 20 minutes)brbrEscape to our lakefront haven on Tims Ford Lake for an unforgettable getaway!brbr• Absolutely no smoking of any kind. This includes marijuana. No pot in any form. No vaping.brbr• Please do not wear shoes throughout the house. There is a shoe tray to the left of the door when you enter. brbr• Please close and lock all windows and exterior door when you leave.brbr• No candles. brbr• Please, nothing but toilet paper should go in the toilet. There’s a little trash bin for everything else.brbr• Please turn off all lights when leaving the house. brbrNOTE: There is new construction taking place and this community is zero lot lines so homes are close together in this gated community. brbrNOTE: The paddleboard and Kayak are available for use and you are responsible for your own safety while using them.
Bed 4

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Bath 3

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Sleep 10

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Exceptional(6)

$486.15

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Private Vacation Home

Modern Charm with Rare Flat Lot, Dock, Game Area

Winchester, Tennessee, United States

Welcome to your perfect lakeside escape! This spacious and beautifully decorated home is designed for comfort, fun, and unforgettable memories. With shuffleboard, ping pong, and plenty of room to spread out, it’s the ideal spot for families, groups, or couples` getaways. Soak up the sun on the double decker dock, cast a line, or enjoy your morning coffee with panoramic lake views. Whether you`re boating, lounging, or exploring the area, this home is your front-row seat to lake life.brbr-Shufflebaord and Ping Pong table ready for you to play in the sunroombr-Fire pit and porch seating where you can sit back and relax while taking in the beautiful water viewsbr-Outdoor enthusiasts will appreciate the dock access with a slip. Fish off the dock, kayak, swim, or just relax by the water.brbrIndoor Comforts:brStep into relaxation as you enter with a stocked kitchen, spacious seating, and fireplace. 4 bedrooms and 3 bathrooms, there`s ample space for everyone, ensuring a comfortable stay. The master suite, located on the main level, features a king-sized bed for comfort. brbr ️ Marinas & Waterfront Diningbr1. Twin Creeks Marina & Resortbr• Location: 91 Slip-A Way, Winchester, TNbr• Features: Boat slips, rentals, waterfront dining, and resort accommodations.br• Contact: (931) 201-4003br• Website: twincreekstfl.com/playhere (Twin Creeks Marina & Resort in Winchester, TN 37398 - 931-201...)br2. Tims Ford Marina & Resortbr• Location: 175 Marina Lane, Winchester, TNbr• Features: Pontoon rentals, RV park, lakeview cabins, fuel dock, and the Hard Dock Café with live music.br• Contact: (800) 722-1164br• Website: timsfordmarina.com (Tims Ford Marina & Resort - Tims Ford Lake Visitors Guide | Winchester, TN)br3. Lakeview Marina & Restaurantbr• Location: 1439 Tims Ford Drive, Winchester, TNbr• Features: Boat, kayak, and paddleboard rentals; fuel dock; quick eats; and an ice cream shop.br• Contact: (931) 967-6711br• Website: lakeviewmarinatimsford.com (Lakeview Marina - Winchester, Tennessee, Lakeview Restaurant & Boat Dock - Tims Ford Lake Visitors Guide | Winchester, TN, Lakeview Restaurant Marina - Winchester, TN (Address, Phone, and Hours))br4. Holiday Landing Marina & Blue Gill Grillbr• Location: 912 Old Awalt Road, Tullahoma, TNbr• Features: Pontoon rentals, covered slips, lakeside cabins, motel, and the floating Blue Gill Grill restaurant.br• Contact: (931) 455-3151br• Website: holidaylanding.com (Holiday Landing Marina - Tims Ford Lake Visitors Guide | Winchester, TN)br________________________________________br Distilleries Within 30 Minutesbr1. Branchwater Distillerybr• Location: 115 2nd Ave NW, Winchester, TNbr• Highlights: Locally crafted moonshines, tastings, and live music in a cozy downtown setting.br• Contact: (931) 636-7556 (10 Best Things to Do in Winchester, TN (for 2025))br2. Jack Daniel’s Distillerybr• Location: 182 Lynchburg Hwy, Lynchburg, TNbr• Highlights: Historic distillery offering guided tours, tastings, and a visitor center.br• Contact: (931) 759-6357br• Website: jackdaniels.com (Twin Creeks Marina & Resort in Winchester, TN 37398 - 931-201...)br3. Cascade Hollow Distilling Co. (George Dickel)br• Location: 1950 Cascade Hollow Rd, Tullahoma, TNbr• Highlights: Scenic distillery tours, tastings, and insights into Tennessee whisky production.br• Contact: (931) 408-2410br• Website: georgedickel.combr________________________________________br Outdoor Recreation & AttractionsbrTims Ford State Parkbr• Features: 3,546 acres of natural beauty with hiking and biking trails, Bear Trace Golf Course designed by Jack Nicklaus, camping sites, and lake access.br• Website: tnstateparks.com/parks/tims-ford (Tims Ford State Park)brOldham Theaterbr• Location: 115 1st Ave NE, Winchester, TNbr• Highlights: Historic theater showcasing movies in a vintage setting.br• Contact: (931) 967-2516 (10 Best Things to Do in Winchester, TN (for 2025))brJail Museumbr• Location: 400 Dinah Shore Blvd, Winchester, TNbr• Highlights: Historic jail turned museum featuring exhibits on local history.br• Contact: (931) 967-0524 (10 Best Things to Do in Winchester, TN (for 2025))brNo parking on grass or roadbrNo petsbrNo smoking in the homebrNo parties or eventsbrMust be 25yrs of age or older to book the property
Bed 4

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Bath 3

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Sleep 16

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Exceptional(6)

$397.58

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Private Vacation Home

Lucky Dozen Lakehouse-Dock, Slip, Kayaks, SUPs

Winchester, Tennessee, United States

Welcome to your lakefront escape, where vintage charm meets modern comfort. Enjoy your coffee as you soak in peaceful water views, then head out on the lake using the provided kayaks, paddleboards, and lilypad. Dock your boat in the slip or unwind on the spacious double-decker dock. When the sun sets, gather around the fire pit or keep the fun going with a game of foosball, test your skills on the arcade machine, or enjoy card games around the unique whiskey barrel card table.brbrHighlights of Your Stay:brDouble-Decker Dock: Soak in breathtaking lake views from the top deck or jump right into the water below.brWater Adventures: Enjoy complimentary paddleboards and kayaks to explore the serene lake at your leisure.brOutdoor Fun: Roast marshmallows around the fire pit, or challenge friends to a match of foosball.brIndoor Entertainment: Relive your favorite classics with the arcade game, or cozy up by the fireplace with a good book.brbrBeyond your retreat, a world of local attractions await just minutes away. Embark on a journey to the legendary Jack Daniel`s distillery immerse yourself in the natural beauty of Tim`s Ford State Park, and explore the scenic wonders of the Elk River. Also, in the area you`ll find Uncle Nearest Distillery and George Dickel distilleries where you can schedule tours and tastings. brbrThere are steps going down to the water with no handrail. There are also steps from the main level to the lower level. The first step down is larger than the other steps.brbrTheir is a trundle bed in the laundry room that someone can sleep on. It pulls out and can be used as 2 twins or put together and used as a king. This is listed as a bed option in the listing and is considered to allow the home to sleep up to 12 people.brbrProperty has seasonal water. TVA will begin reducing water levels in October and will return to normal levels in May. During this time the dock will not be accessible with a boat and no swimming off the dock during this timeframe. You will not be able to sit on the dock Late November-April.brMust be 25yrs of age or older to book the propertybrNo Parties or Events-This is a quiet neighborhood with neighbors close by, please be mindful of noisebrNo PetsbrNo Smoking in the Home
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Bath 2

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Sleep 12

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