Vacation rentals with outdoor seating in Winchester

A spacious home is presented with a welcoming porch, surrounded by a large green lawn. The house features large windows and a distinctive green roof, complemented by trees in the background. The setting provides an open and inviting atmosphere.

4.82 out of 5 average rating, 127 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

4.85 out of 5 average rating, 194 reviews

A comfortable living area is observed, featuring a light-colored sectional sofa and a dark wooden coffee table. Large windows provide natural light, while a rustic dining table and chairs are visible in the background. Decorative wall art and assorted accents highlight the cozy atmosphere.

Cabin in Winchester

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)

4.93 out of 5 average rating, 266 reviews

The charming exterior of a tiny mountain cabin is framed by lush greenery and vibrant pink flowers. A wooden porch with a railing provides access to the cabin, featuring a gas grill and a few outdoor chairs for relaxation.

Cabin in Morrison

Little Mountain Cabin Extraordinary Secluded View!

Secluded, PRIVATE tiny mountain cabin offers solace for your soul! Altamont, TN. Expansive mountain views from private front porch. ESCAPE the world. 20 mn to State Parks, hike, waterfalls. An awesome slice of heaven tucked on a mountainside. 1,000 acres of wilderness surrounds your cabin with stunning South Cumberland Mountain views. Pristine PRIVATE setting. Mountain sunrises. stars, moonrises. Serenity, peace. Refresh, restore. Charming cabin w/kitchen, loftbed, full bath. Firepit, heat/ac.

Top guest favorite

The exterior of the property features a unique sloped roof with a combination of stone and wood materials. Surrounded by greenery, the entrance is approached via a paved path that leads to a welcoming entrance area. Outdoor seating is visible on the balcony, nestled among the trees.

Home in Manchester

4.93 out of 5 average rating, 148 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 favorite

A welcoming porch area features vibrant red flooring, complemented by a metal table and chairs. A vintage mailbox stands prominently, while a grill and a chiminea add to the rustic charm. Potted plants are placed nearby, enhancing the outdoor living space.

Cabin in Estill Springs

4.96 out of 5 average rating, 267 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 favorite

An outdoor seating area features blue and white lounge chairs arranged around a central fire pit. The shaded porch swing offers a serene view of the lake, framed by lush greenery. The dock and numerous boats can be seen in the background.

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!

A serene outdoor space features four red Adirondack chairs arranged around a circular stone fire pit. The scene is illuminated by the warm glow of the setting sun, casting soft light through the surrounding trees and reflecting on the tranquil lake in the background.

4.88 out of 5 average rating, 113 reviews

Dock on Lake! Walk to Downtown Shops/Rest/Movies!

Charming, *Pet Friendly* well-loved 1950s lake house on Tim’s Ford Lake. Walking distance to grocery and downtown movie theatre, boutiques, restaurants and library. Near Twin Creeks marina/restaurant where you can rent boats. While here, you can swim at the dock; play darts, checkers or fuse ball; go out on the lake; walk to the Oldham Theatre; go hiking in Tim’s Ford State Park or nearby Sewanee; go to the Tullahoma drive-in theatre; or visit nearby Jack Daniel’s distillery.

4.82 out of 5 average rating, 157 reviews

The exterior of a two-story cabin is seen, featuring a sloped roof and a welcoming front porch with two chairs. Surrounding the cabin, a well-maintained lawn and gravel pathway create an inviting atmosphere amidst a wooded landscape.

Cabin in Winchester

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.

4.98 out of 5 average rating, 289 reviews

A waterfront view showcases the cabin nestled among lush trees, reflected in the calm water. Soft evening hues illuminate the sky, creating a serene backdrop for the natural landscape.

Cabin in Coalmont

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, 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.

4.93 out of 5 average rating, 169 reviews

A spacious living room showcases wood-paneled walls and ceiling. Two comfortable sofas and an armchair are arranged around a wooden coffee table. Decorative pillows add color. Natural light filters through light-filtering shades on the windows, and a large framed photograph is displayed on the wall.

Cabin in Tullahoma

Cozy Cabin close to Tims Ford Lake & Jack Daniels

A cozy cabin awaits you located close to Tim's Ford Lake-1/2 mile from Holiday Landing Marina & Blue Gill Restaurant. Lynchburg, home to popular Jack Daniel's Distillery-only 12 miles away; Nashville-90 mins. Made from handcrafted red cedar, you will be met with a woodsy aroma when entering. Special touches can be found throughout including Jacuzzi tub! Truly a unique wooded cottage, equipped to ensure a relaxing getaway. Pet friendly with an additional pet fee.

4.98 out of 5 average rating, 105 reviews

A wooden bridge is seen leading toward a treehouse, surrounded by tall trees with thin branches. This pathway is elevated, providing a view of the forest floor blanketed in fallen leaves.

Treehouse in Tracy City

Owl’s Nest Treehouse Getaway w/ Hot Tub & Fire Pit

Reconnect with nature at this unforgettable treehouse escape. One of the few treehouse cabins in Tracy City, located on 2 acres of beautiful wooded land. We are less than 1 mile from South Cumberland State Park with access to hiking trails, creeks, and Mountain views. Enjoy the sounds of the woods on our elevated deck, or relax in the private hot tub down below. The newly renovated outdoor space includes a grill, fire pit, pond & hanging egg chairs.

The exterior view showcases a Craftsman-style house bordered by a spacious deck. A wooden pergola arches over part of the deck, enhancing the outdoor living space. The yard features manicured grass and is enclosed by a black fence for added privacy.