Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favourite

Home in Winchester

4.96 out of 5 average rating, 108 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!

Guest favourite

Cabin in Lynchburg

4.95 out of 5 average rating, 151 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.

Guest favourite

Cottage in Pelham

5.0 out of 5 average rating, 394 reviews

The Milk Barn Cottage

Built in the late 1940's as a working milk barn, the Milk Barn Cottage is 800 sq. ft of cozy comfort. The cottage is near the foot of Monteagle Mountain in the beautiful Pelham Valley. We are half-way between Nashville and Chattanooga, about 2 miles off exit 127 on I-24. The Caverns is about 8 minutes away. Pelham has a coffee shop and quaint restaurants to visit plus all of the natural beauty in our area. We are also just 13 miles from Sewanee and the University of the South.

Guest favourite

Tiny homes in Tullahoma

5.0 out of 5 average rating, 22 reviews

Whiskey Woods Retreat-Hot Tub

Need a Reset? Unwind to the sounds of nature and relax in the hot tub! This romantic getaway is the ultimate couples retreat and is equipped with everything you need including a 55 inch flat screen with Netflix and fiber internet. Surrounded by 230 acres of farmland and wildlife! Experience a unique escape like no other for privacy and nature! Nearby cities: Lynchburg, Tullahoma, Winchester Nearby attractions: whiskey tours, waterfalls, mountains, Tim's Ford Lake

Guest favourite

Guesthouse in Manchester

5.0 out of 5 average rating, 19 reviews

1 Bed 1 Bath Carriage House

The carriage house is located behind the main house with its own entrance and its own private balcony. This spacious one bedroom carriage house has a queen size bed and separate living room with sleeper sofa and kitchenette with a table. You are welcome to enjoy the park-like setting grounds as well as a gazebo with swing chairs and picnic table area. For stays over one week, there is a washer and dryer on the bottom level. You will have to ask hosts prior for access.

Guest favourite

Apartment in Hillsboro

4.94 out of 5 average rating, 164 reviews

The Wright Place Apartment

Precious, cozy efficiency apartment with a queen size Serta sofa bed and a full size 8” foam loft bed. Full kitchen with large bar for eating. All dishes and pots and pans supplied. Nice big shower. Private entrance with pergola and fire pit. One hour from Chattanooga and one hour from Nashville, with hiking and nature sites within 20-30 minutes. If you are arriving late in the evening, you may make a request for the sofa bed to be made prior to your arrival.

Guest favourite

Home in Winchester

5.0 out of 5 average rating, 80 reviews

Historic Home - Walk to Downtown Winchester TN!

Welcome to our beautifully renovated historic home just three blocks from the downtown Winchester square. Walk to see a movie at our historic two-screen theater, grab pizza at Piezan, coffee at Walnut Hill, or dinner and drinks at our new upscale Tavern - Filo's. Of course, we are so close to Tim's Ford Lake and all that has to offer: fishing, boating, water sports. We restored this home from the ground up to create the perfect Airbnb experience.

Guest favourite

Cottage in Winchester

4.91 out of 5 average rating, 45 reviews

Peaceful 3 Bedroom Modern Cottage

Relax with the whole family at this peaceful retreat. Conveniently located in Winchester adjacent to Twin Creeks Village. Less than a mile to boat ramp, marina, Drafts and Water Crafts restaurant, Walnut Hill Coffee shop, Piezan Pizzeria, Orange Blossom restaurant, and public beach. Plenty of space for boat parking or rent one at the marina. Less than a half hour to Sewanne/ Monteagle community. Approximately 20 min to Jack Daniels Distillery.

Guest favourite

Home in Winchester

5.0 out of 5 average rating, 5 reviews

Lakeside Retreat Marina/Pool, Golf Cart, Game Room

Discover luxury living at your lakeside retreat in the prestigious Twin Creeks Marina subdivision on Tims Ford Lake. This exquisite home features indoor and outdoor fireplaces, a game area with foosball and arcade, plus a 6-seater golf cart for exploring. Just minutes away, enjoy a pool and the convenience of Twin Creeks Marina's amenities, including a restaurant, boat rentals, snacks, and gas. Your ultimate vacation experience awaits!

Guest favourite

Barn in Tullahoma

4.97 out of 5 average rating, 127 reviews

The Barn @ Dreamcatcher Farm

Make sure to “heart” our listing so you can find us when you are ready to book. Did someone say baby goats?!?! Live the farming dream in Middle Tennessee on Dreamcatcher Farm. Our 13 acre farm is home to Nigerian Dwarf goats, Santa Gerturdus cattle, a couple of horses, and the Labs and barn cats that run the operation. Come enjoy some down time in a quiet country setting with friendly farm animals.

Guest favourite

Guesthouse in Lynchburg

4.96 out of 5 average rating, 221 reviews

Country Guest House

My Guest house is located in TN. just 5 miles south of the Lynchburg town square. Local attractions include: Distillery tours, an aviation museum, boating, shopping and dining. Please look at my Guidebook. You can find it by scrolling down this listing to "Where you'll be", then click on the "show more" link. The link to the guidebook is there. It will give you lots of things to eat see and do.

Guest favourite

Guest suite in Manchester

4.98 out of 5 average rating, 352 reviews

Creekside at Rutledge Falls

Cozy nest right on the creek. Lots of privacy. Hiking trails and Waterfalls nearby. Listen to the water from a porch swing overlooking the creek. We have a double recliner for movies and popcorn. This efficiency apartment has a private entrance with private covered porch and a full kitchen. Work area with Wi-Fi. Pets are welcome - must be free of fleas and ticks.