Kid-friendly holiday rentals in Winchester

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Top-rated family-friendly rentals in Winchester

Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.

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Superhost

Home in Winchester

4.82 out of 5 average rating, 130 reviews

Beautiful And Spacious Fully Renovated Farmhouse

Beautifully renovated 4 bedroom, 3 bathroom, spacious home. Roku TV, fast internet, large yard where you can see the sunrise in the back of the home and the sunset in the front of the home. Very close to the lake (less than 10 minute drive), close to many great nature spots, and University of the South, Downtown Winchester area, and the famous Jack Daniels Distillery. 8 people can be comfortably accommodated, and if extra sleeping arrangements are needed, we have a comfy couch! W

Superhost

Cabin in Winchester

4.85 out of 5 average rating, 194 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)

Top guest favourite

Home in Manchester

4.94 out of 5 average rating, 155 reviews

Chalet 638 - state park, golf & The Caverns

Short walk to a state park with golfing. This first floor living space has a kitchen, walk-in closet, large wood fireplace, workout equipment, washer/dryer, grill, fire pit and lots of space. Old Stone Fort Archeological Park with multiple hiking trails, fishing, canoeing and a $9 a round golf course are seconds away. Close to I-24 this centrally located Tennessee property gives equal access from Nashville to Chattanooga. Explore parks, vineyards, distilleries and Tennessee history from here.

Top guest favourite

Tiny home in Winchester

5 out of 5 average rating, 44 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

Cabin in Estill Springs

4.96 out of 5 average rating, 268 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.

Top guest favourite

Home in Winchester

4.96 out of 5 average rating, 119 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 Coalmont

4.98 out of 5 average rating, 294 reviews

The Coalmont Cabin - Waterfront Retreat w/ HOT TUB

The Coalmont is a 4 acre waterfront retreat on top of the South Cumberland Mountains of Tennessee, between Nashville and Chattanooga. This 460 sq ft "tiny" cabin sleeps up to 4. Amenities abound with boats, hot tub, fishing, zip line, lawn games, large decks for gathering, fire pit, and beautiful scenery. Perfect retreat for couples looking for a romantic getaway, families wanting to unplug and reconnect with quality time, or anyone looking for a quiet place to work remotely.

Superhost

Cabin in Winchester

4.82 out of 5 average rating, 157 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.

Guest favourite

Home in Winchester

4.93 out of 5 average rating, 122 reviews

Lovely Lake View Home at Twin Creeks Marina

This Craftsman-style, lake-view house is located in the private, gated lakeside community of Twin Creeks Village at scenic Tim's Ford Lake in Winchester, TN. It features an open floor plan with 4 bedrooms, 3 baths, game room, screened porch and huge deck overlooking the lake. Use the included golf cart to go to the swimming pools, marina, bar & grill or on-site convenience store. Information on boat & jet ski rentals are available at the marina shop.

Guest favourite

Home in Chattanooga

4.98 out of 5 average rating, 181 reviews

Our Catty Shack

Oliver and Lacey (the cats) would love to welcome you to Our Catty Shack! ***NOTE: Our Catty Shack comes WITH CATS and WITHOUT TV!*** This spiritual retreat is nestled between imposing ridgelines, abuts a state forest, and faces the powerful Tennessee river. Enjoy dramatic sun and moon rises. Luxuriate in the hot tub. Feast your eyes on the views. Only 15 minutes to downtown Chattanooga - with the peace of the country - have it all here.

Top guest favourite

Barn in Tullahoma

4.98 out of 5 average rating, 178 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

Campervan/Motorhome in Sewanee

4.93 out of 5 average rating, 197 reviews

Airstream #97 at The Grove

Sleep in a vintage 1997 Airstream! Fully updated with modern comforts, #97 is nestled in our forest campground, the perfect spot for your laid back Mountain getaway. The Grove at Natural Bridge features 3 vintage Airstreams, a shared well appointed bathhouse and restrooms. Located just a short drive (2.2 miles) from The University of the South and walking distance to Natural Bridge State Park.