Holiday rentals with a patio in Winchester

4.94 out of 5 average rating, 225 reviews

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

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.

4.97 out of 5 average rating, 188 reviews

An aerial view of Twin Oaks reveals the tiny house surrounded by a winding pathway lined with warm outdoor lights. A cozy fire pit area is set with stone seating, inviting relaxation in the tranquil wooded setting.

Tiny home in Tracy City

Twin Oaks tiny house at The Retreat at Waters Edge

Nestled among the oak trees on Monteagle mountain with amazing views of the Fiery Gizzard reservoir, Twin Oaks tiny house is the perfect getaway! Explore the outdoors on hiking trails that lead to waterfalls, see concerts and enjoy eateries, and it's all so easy to get to! Lots of glass that brings the outdoors in if you just want to relax. Each season brings its own unique perspective. Twin Oaks is truly a one-of-a-kind experience. Stay one night or stay a month, you'll love your time here!

4.99 out of 5 average rating, 153 reviews

A spacious king bed is featured in the foreground, adorned with neutral-toned linens. The tent's large mesh window showcases expansive views of rolling hills and a serene sky, creating a connection to the surrounding nature.

Tent in Altamont

Luxury Safari Tent | 15 Mins to Waterfalls & Hikes

Soak in sweeping mountain and valley views from your private hot tub at this remote, luxury safari tent. Unwind on a plush king bed, sip wine beside the glowing fire feature, and bask in unforgettable sunrises and sunsets. Surrounded by nature, peace, and starry skies, this hidden gem is the perfect escape. Just minutes from waterfalls and hiking, it’s glamping at its most magical—serene, stylish, and tucked far away from it all. Reconnect with what matters: nature, stillness, and yourself.

4.99 out of 5 average rating, 73 reviews

A modern tiny home is surrounded by open grass fields, featuring a welcoming porch with wooden steps. Large windows provide natural light, while the exterior showcases a black siding and a gable roof. A gravel path leads to the entrance, enhancing accessibility.

Tiny home in Winchester

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.

4.94 out of 5 average rating, 102 reviews

The exterior of the cabin is shown, featuring a contemporary design with dark grey siding and large windows. A covered porch extends from the front, offering a view of the surrounding landscaping with shrubs and small trees. The tranquil lake is visible in the background.

Cabin in Tracy City

Highpoint Hideaway A | Lakefront Home | WatersEdge

Set upon one of the largest waterfront lots in the community, this tiny home offers a unique experience that's perfect for couples, friends, or family. You'll be enchanted by the tranquility of the lake as it stretches out before you, providing a serene backdrop to your stay. The heart of this property is its outdoor living spaces (2 large decks, complete with outdoor seating and a grill) as evening falls, gather around the fire pit to roast marshmallows, share stories, and make memories.

4.96 out of 5 average rating, 135 reviews

An A-frame cabin is nestled among tall trees, showcasing a modern design with large glass windows. A wooden deck surrounds the entrance, featuring a seating area with chairs and a fire pit. The outdoor area is partially landscaped with natural ground cover.

Cabin in Monteagle

Modern Monteagle A-frame with Hot Tub

Welcome to Camp Mae, a Scandinavian inspired A-Frame stay in Monteagle, TN. Minimalist designed yet elegant, offering the perfect escape- minutes from the Fiery Gizzard hiking trail and Monteagle. Relax in the hot tub or gather around the fire pit. For eco-conscious travelers, we provide an electric car charger. Experience seclusion of the mountains while only minutes from world class hiking, local restaurants and shops. This retreat harmonizes luxury with nature in a serene setting.

4.98 out of 5 average rating, 166 reviews

The tiny home sits nestled by the waterfront, surrounded by trees. A large deck features two lounge chairs and a hot tub, with string lights illuminating the area. A fire pit and seating are positioned near the water, enhancing the serene outdoor environment.

Tiny home in Coalmont

The Coalmont Cove - Romantic Lakefront Escape

The Coalmont is a 4 acre waterfront retreat on top of the South Cumberland Mountains of Tennessee, between Nashville and Chattanooga. The Coalmont Cove is a tiny home that sits in the cove of a private lake. The definition of relaxation with adventure only minutes away, you'll find elevated decor, an inviting outdoor space, and beautiful scenery. The perfect retreat if you’re looking for a romantic getaway or a quiet place to disconnect or work remotely (1 GB fiber optic internet).

4.93 out of 5 average rating, 105 reviews

A quaint off-grid cabin is surrounded by trees, featuring an inviting porch with string lights and a wooden deck. A dining table is positioned beside a covered outdoor kitchen, complete with essential amenities. Two chairs are placed near the entrance, setting a comfortable atmosphere.

Cabin in Sequatchie

Fireside Cabin on the Bluff

Welcome to your private off-grid cabin on a picturesque bluff in Sequatchie, TN. If you’re looking for solitude, stunning views, and a rustic but comfortable escape, this is the spot. The cabin offers a simple “glamping” experience—cozy, peaceful, and close to nature. It’s best suited for guests comfortable with outdoor-style stays who don’t need hotel-level amenities like a TV or indoor shower. If you prefer a more modern setup, please explore our other listings on the property.

A modern structure features a sleek black exterior with wooden shutters. A covered porch is highlighted by two chairs and a potted plant, inviting relaxation. Lush greenery surrounds the home, providing a serene outdoor environment.

5 out of 5 average rating, 46 reviews

The Hangout on Heath Lane

Enjoy a peaceful experience at this centrally-located home. The Hangout is half a mile from the beautiful Twin Creeks Marina and 1 mile to historic downtown Winchester! Other local attractions include: -Grab a coffee and enjoy a tasty breakfast or lunch at Walnut Hill Coffee Shop -For a delicious, upscale dinner, be sure to visit Filo's Tavern -Head out for a tour and tasting at Jack Daniels Distillery -Grab some tickets to the Cavern's for a memorable concert experience.

4.94 out of 5 average rating, 197 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.

5 out of 5 average rating, 18 reviews

Colorful Adirondack chairs in vibrant green, red, and blue are arranged around a stone fire pit, overlooking a serene lake. The view includes a dock and lush greenery, framed by trees and a pastel sky at sunset.

Apartment in Winchester

Hook, Wine, Sinker Unit B

Welcome to Hook, Wine, & Sinker, your lakeside retreat! This charming home is perfect for relaxation, fun, and a waterside fire pit for relaxing with friends and family. Challenge your guests to ping pong, foosball, or to one of the exciting arcade games. Swim off the dock or embark on lake adventures with your complimentary kayaks and paddleboards. Ideal for families and friends seeking both tranquility and excitement, this home promises a great escape!

4.97 out of 5 average rating, 156 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.

Popular amenities for Winchester Holiday Houses with Outdoor Verandahs

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.95 out of 5 average rating, 22 reviews

A narrow hallway features warm wooden flooring and neutral-colored walls. On one side, a kitchenette with counter space and modern appliances is visible. A round table with two cushioned stools is positioned nearby, alongside a wall-mounted television. Soft lighting enhances the cozy setting.

Apartment in Shelbyville

The Bedford @ Glass Hollow

4.9 out of 5 average rating, 21 reviews

A cozy living area features large windows that allow natural light to illuminate the space. An inviting seating arrangement includes a brown sofa and two metal tables. A dining table is positioned nearby, and a mounted television is visible against the textured wall.

Apartment in Shelbyville

The Whiskey Room @ Glass Hollow

4.76 out of 5 average rating, 37 reviews

A well-appointed sleeping area features a firm spacious bed neatly arranged with fresh linens and towels. Bedside tables are positioned on either side, accompanied by stylish table lamps. A clothing rack is available for guest convenience, and natural light enters through a nearby window.

Apartment in Monteagle

Adorable & Stylish Studio in Monteagle, TN!

Apartment in Village of Pelham

A modern two-story building is set against a natural backdrop of rolling hills. The exterior features a sleek grey finish, with large windows and a wooden deck accessible by stairs. An open area with gravel offers ample space for outdoor activities.

4.95 out of 5 average rating, 42 reviews

Mountain Retreat Overlook 7 min walk to Caverns

4.9 out of 5 average rating, 50 reviews

An inviting studio suite is presented with a spacious layout. A comfortable leather sofa is positioned in front of a sleek coffee table, with a firm bed featuring soft linens in the background. The kitchenette and dining area are visible, providing a functional and modern atmosphere.

Apartment in Monteagle

Studio with Kitchenette

4.83 out of 5 average rating, 58 reviews

Apartment in Shelbyville

Cute apartment on the river!

A functional kitchen features teal cabinetry and a black stove. A wooden bowl sits at the center of a dark table adorned with a floral yellow tablecloth. Wall art and decorative tiles add character, while natural light brightens the workspace.

Apartment in Winchester

Just Around the Corner

Apartment in Winchester

New place to stay

Winchester Basecamp -Near Square and Tims Ford

Holiday House Rentals with a Verandah

A covered porch features comfortable seating arrangements, with two cushioned chairs positioned around a circular wooden table. A spacious grassy yard extends beyond the porch, framed by lush greenery and trees. The tranquil waters of Tims Ford Lake can be glimpsed in the background.

5 out of 5 average rating, 22 reviews

Sunset Cottage +Dock on Tims Ford Sleeps 12

A close-up view features a stylish light fixture beside a dark, round table. The background showcases a textured wallpaper with bold, black plant motifs. A soft white bed is highlighted, accompanied by a decorative pillow with black and white fringe.

5 out of 5 average rating, 19 reviews

Location, location, location!

4.96 out of 5 average rating, 132 reviews

A modern cabin is shown with a sleek design, featuring a covered porch with a rail and stone base. Large windows allow natural light to enter, surrounded by trees in autumn colors. A grassy area is visible in the foreground.

Home in Tracy City

Cozy Two Bedroom Cabin with Hot Tub in Waters Edge

5 out of 5 average rating, 17 reviews

The exterior of the property features a traditional single-story home with a welcoming porch and a spacious front yard. A covered carport is adjacent to the house, providing shelter. Lush green trees frame the scenic view, enhancing the overall appeal of the property.

Home in Estill Springs

Timberhill Home-Walk to the Lake!

5 out of 5 average rating, 61 reviews

An open-concept area is featured, showcasing a rustic wooden dining table surrounded by stools. Modern pendant lights hang above, illuminating the space. A cozy seating area with a large TV is visible in the background, complemented by light-colored walls and warm wooden flooring.

Home in Tullahoma

Whiskey Trails Cottage

The exterior of a modern custom home is displayed, featuring a combination of white and blue siding. A spacious green lawn surrounds the property, while a circular seating area with chairs is positioned in front of the home, inviting outdoor relaxation.

5 out of 5 average rating, 20 reviews

Barefoot Dreams

Home in Village of Pelham

The exterior of the home is showcased, framed by mature trees providing ample shade. The well-kept lawn features a grassy area leading to the entrance. A bench is visible in the distance, enhancing the tranquil outdoor setting.

4.99 out of 5 average rating, 77 reviews

Meme's Place- 6 miles from The Caverns!

4.96 out of 5 average rating, 102 reviews

A spacious living area features a large sectional couch and a wooden coffee table with two cups. Natural light fills the room through wide windows, and a mounted television displays a scenic landscape. A stone wall adds texture and warmth to the space.

Home in Guild

Nickajack Overlook

Other holiday rentals with a patio

The entryway features a welcoming porch with two comfortable seating areas, one composed of wooden rocking chairs and another wicker chair. A decorative welcome mat greets guests, while a handcrafted wreath adorns the door, inviting all into the cozy interior beyond.

4.73 out of 5 average rating, 22 reviews

Lakeside Luxe | Lake + Pool Access

4.98 out of 5 average rating, 61 reviews

A golf cart is parked in the driveway in front of a cottage, featuring a covered porch with two blue chairs. The cart is equipped with comfortable seating, black detailing, and all-terrain tires, designed for easy access to the nearby marina.

Home in Tullahoma

"Dock Holiday" Retreat on Tim's Ford Lake.

4.93 out of 5 average rating, 42 reviews

The exterior view displays a charming red and white cottage surrounded by greenery. A spacious front porch with black chairs invites relaxation. Kayaks are neatly arranged beneath the deck alongside a golf cart, offering easy access to nearby docks for boating.

Home in Tullahoma

Cottage Retreat @ Tims Ford

A gated entrance is presented, featuring sturdy metal gates flanked by stone pillars. A clear sky is visible above, with several houses lining the street beyond the gates. Lush greenery is situated near the entrance, providing a serene atmosphere.

4.88 out of 5 average rating, 8 reviews

Lake House Dreams

The exterior of a modern lakefront home is shown, featuring a clean design with light-colored siding and dark accents. A driveway leads to the entrance, while lush greenery surrounds the property, and the tranquil lake is visible in the background.

5 out of 5 average rating, 23 reviews

Lakeshore Modern- steps to water

4.9 out of 5 average rating, 52 reviews

An outdoor deck features a hot tub, surrounded by lush greenery and trees. Cozy seating areas with plush cushions are positioned nearby, alongside a circular dining table with wicker chairs. Sunlight filters through the trees, enhancing the tranquil atmosphere.

Home in Monteagle

Tiny Home Retreat w/ Hot Tub in Monteagle, TN!

4.98 out of 5 average rating, 53 reviews

The exterior of Stars Hollow House is framed by lush greenery, showcasing a charming two-story design with a covered porch. A tall stone chimney rises, contributing to the cozy aesthetic. A landscaped garden with smooth stones and flowering shrubs enhances the natural beauty surrounding the home.

Tiny home in Tracy City

3 Bed Nature Getaway in Tiny Home w/ Lake Access

A spacious covered dock extends over the tranquil waters, featuring two large swings for relaxation. Kayaks are positioned nearby, surrounded by lush greenery. Steps lead up from the dock to the home situated among the trees, creating a serene lakeside setting.