Holiday houses in Winchester

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Top-rated holiday rentals in Winchester

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

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Guest favourite

Cabin in Estill Springs

4.95 out of 5 average rating, 240 reviews

Holliday Hide Away

1200 sq. ft. very rustic converted pole barn. The floors are stained concrete and the walls are rough saw mill hewn poplar boards. Located on 3 acres of beautiful well kept property. It does not border the lake but is surrounded by Tims Ford Lake and less than 5 minute drive to 3 boat docks and launches. Close to restaurants, shopping venues, hiking trails, water falls and golfing. Pool table, cornhole set, board games & cards in cabin. Visit historic Franklin County and surrounding areas.

28 Mar – 4 Apr

$1,430 AUD total

Guest favourite

Home in Winchester

4.96 out of 5 average rating, 106 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!

25 June – 2 July

$5,154 AUD total

Guest favourite

Cabin in Lynchburg

4.95 out of 5 average rating, 147 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.

7 – 14 May

$1,909 AUD total

Guest favourite

Cottage in Pelham

5.0 out of 5 average rating, 388 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.

25 Oct – 1 Nov

$1,850 AUD total

Superhost

Cabin in Winchester

4.81 out of 5 average rating, 151 reviews

VACATION CABIN - Sunday Morning Rentals

We are in Winchester, TN, and are located within a SHORT 5 MINUTE WALKING DISTANCE to Tims Ford Lake and Devil Step Boat Launch. Sunday Mornings Rentals is a completely equipped cabin that ensures a relaxing getaway. Perfect for all of your boating, fishing, and hiking recreations. The charming town square is approximately 5 miles from the rental - offering unique shops, a quaint theatre, and restaurants that are sure to provide enjoyment for everyone. PETS NOT ALLOWED.

25 Dec – 1 Jan

$2,098 AUD total

Guest favourite

Cottage in Hillsboro

4.86 out of 5 average rating, 255 reviews

Eva’s Country Cottage

Our little cottage is halfway between Nashville and Chattanooga. It is only an hour to either city. The Caverns, Bluegrass Underground, is just 15 minutes away. Bonnaroo is just 7 miles up the road and Jack Daniels Distillery and Lynchburg are only 30-45 minutes away. Large lakes and winding rivers are not far away. A quaint older building that was originally built as a church, it was converted into a home in 1964 and has recently been updated and remodeled.

25 Nov – 2 Dec

$1,040 AUD total

Guest favourite

Home in Winchester

5.0 out of 5 average rating, 78 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.

10 – 17 Mar

$1,996 AUD total

Guest favourite

Cottage in Winchester

4.9 out of 5 average rating, 41 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.

8 – 15 July

$1,308 AUD total

Guest favourite

Guesthouse in Tullahoma

4.99 out of 5 average rating, 81 reviews

Woodland Ct. Cottage

This one bedroom guesthouse is the perfect stay for you and your loved ones! Conveniently located in the heart of Tullahoma! Within walking distance of just about everything you need from grocery stores, restaurants, local coffee shops, and more! We are located just 20min from the famous Jack Daniels Distillery and 15 min from George Dickle! If you are interested in some nearby hiking be sure and check out Short Springs and Rutledge falls!

7 – 14 July

$1,506 AUD total

Guest favourite

Barn in Tullahoma

4.97 out of 5 average rating, 124 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.

29 Mar – 5 Apr

$1,381 AUD total

Guest favourite

Cabin in Winchester

5.0 out of 5 average rating, 17 reviews

The Cabins At Rivers Edge

Tucked in the hills of Tennessee, we are located on the beautiful Elk River. Come enjoy over a 1/2 mile of private access river frontage. Whether you're looking for a guided fishing trip, a 10 minute drive to downtown Lynchburg to visit Jack Daniels Distillery, a day on the water at Tim's Ford Lake, or a peaceful weekend to unplug, you can find it all At Rivers Edge.

13 – 20 May

$2,047 AUD total

Guest favourite

Guest suite in Manchester

4.98 out of 5 average rating, 349 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.

17 – 24 Sept

$1,497 AUD total