Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favourite

Home in Winchester

5.0 out of 5 average rating, 22 reviews

Cozy Lake Cottage W/ Kayaks, SUPs, Pool & Firepit

Enjoy lake living at one of the newest lakefront neighborhoods on Tim's Ford Lake. This cozy cottage is in a beautiful gated community and has lake views from the front porch. It is only a 1 min walk to the community pool overlooking the lake and direct lake access for kayaks and paddleboards that we include for you! This beautiful home also boasts a hot tub, fire pit, and game room for your family to enjoy! You are also centrally located and only 5 min from Twin Creeks Marina and downtown!

Nov. 8 – 15

$275 CAD per night

Guest favourite

Cabin in Estill Springs

4.95 out of 5 average rating, 239 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.

Oct. 26 – Nov. 2

$182 CAD per night

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!

Feb. 20 – 27

$747 CAD per night

Guest favourite

Cabin in Lynchburg

4.95 out of 5 average rating, 146 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.

May 6 – 13

$248 CAD per night

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.

Feb. 1 – 8

$271 CAD per night

Guest favourite

Home in Winchester

5.0 out of 5 average rating, 13 reviews

Walk to Downtown Winchester! Renovated Cottage

Totally renovated cottage, just completed and ready for guests! This home is just one block from downtown Winchester but our little pocket is very calm and peaceful. It has 2 bedrooms and 1 bathroom and is around 1,000 sq feet. Original hardwood in living room and bedrooms have been refinished. An oversized kitchen with brand new cabinets, appliances, and countertops is the perfect place to relax and have coffee. Washer and dryer are supplied for guests’ convenience.

Apr. 19 – 26

$214 CAD per night

Guest favourite

Apartment in Hillsboro

4.94 out of 5 average rating, 156 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.

Dec. 19 – 26

$97 CAD per night

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.

Jun. 24 – Jul. 1

$172 CAD per night

Guest favourite

Barn in Tullahoma

4.97 out of 5 average rating, 123 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.

Oct. 4 – 11

$176 CAD per night

Guest favourite

Guesthouse in Lynchburg

4.96 out of 5 average rating, 219 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.

May 18 – 25

$131 CAD per night

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.

May 1 – 8

$279 CAD per night

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.

Nov. 23 – 30

$193 CAD per night