Pet-friendly holiday rentals in Winchester

A cozy bedroom features a spacious bed with soft, patterned bedding. Above the bed, a framed artwork adds a touch of color. A closet with neatly arranged shelves and a blue dresser is visible, providing ample storage. Soft lighting enhances the room's atmosphere.

4.93 out of 5 average rating, 126 reviews

Relax & Unwind in Cozy Farm Stay 7 mins from I-24

Come enjoy a cozy getaway in Sewanee! You’ll love this space because of the location, amenities, and cleanliness. This home is best suited for couples, small families and those traveling with pets. This mobile home has an open layout. It’s 700 square feet and sits near the woods, off a back road, bordering a horse pasture and trees. It has a spacious fenced-in yard. Located 7 minutes off I-24 for those driving thru, and a short walk or drive from Mountain Goat Trail if you want to walk or jog.

4.89 out of 5 average rating, 468 reviews

A rustic log cabin is set within a spacious green yard, surrounded by trees. A gravel path leads to the entrance, with stairs ascending to the front porch. Windows provide views of the natural landscape, reflecting a serene outdoor environment.

Home in South Pittsburg

Martin Springs Cabin.

This country cabin is a great base for exploring the nearby South Cumberland Park and surrounding area. Convenient to Sweetons Cove Gulf, The Caverns, Adventure Offroad Park, Sewanee, Monteagle, South Pittsburg/Cornbread Festival, Jasper Highlands. right next to I-24. You can't see any other homes from the cabin and adjacent meadow. Year round creek in the property. Meadow trail. New Hot Tub and all new Tuft & Needle mattresses for 2022! Basic amenities provided. Includes Wi-Fi and DVD player.

4.92 out of 5 average rating, 407 reviews

Cabin in Tracy City

Waterfall Log Cabin

Cozy Log Cabin just feet away from the top of our 2 magnificent private waterfalls. The Falls at Sewanee Creek is located in America’s most biodiverse area on Tennessee's Eco-Rich Cumberland Plateau. Walk to the observation bench at the top of the biggest 50 ft waterfall. Follow the trail behind the falls. Adventure awaits on a rugged, bouldering hike, past cascades and the second big waterfall to two private caves. Disclaimer: Flow of all Waterfalls is subject to weather fluctuations.

4.95 out of 5 average rating, 278 reviews

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

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.

4.9 out of 5 average rating, 288 reviews

A charming cottage is nestled among tall trees in a wooded area. The building features large windows that invite natural light, while a gravel pathway leads to the entrance. Dense greenery surrounds the cottage, creating a tranquil atmosphere.

Tiny home in Monteagle

The Nest at The Retreat @ Deer Lick Falls

The Retreat offers a cozy cottage for down time & you have the option to hike trails down to falls area, socialize with other guests or sit and have your own Fire in our fire pit on the property and just relax! Local Restaurants minutes away, lake access 10 minutes away with beautiful woodsy setting perfect for getting away from the hustle of everyday life! Covered patio for relaxing and you can eat outdoors with a grill guests can use and a fully equipped kitchen if you choose to cook.

4.88 out of 5 average rating, 137 reviews

The tiny home features a modern exterior with dark siding and a metal roof, set among trees. A covered porch with seating is visible, along with outdoor lighting that highlights the natural landscape. The surrounding area is partially covered in leaves, emphasizing the woodland setting.

Tiny home in Monteagle

Sweet Dee's Tiny Home

FEATURES A HOT TUB! Relax in style at Sweet Dee's (formerly listed as The Alexander), a luxury tiny home in the Retreat at Deer Lick Falls. Serene, tranquil, rustic, wooded setting with relaxation stations throughout the community. The Retreat at Deer Lick Falls is a gated luxury tiny home community in southeast Tennessee. The community is only 15 minutes from the University of the South in Sewanee. Guests of the Retreat also have access to Retreat at Waters Edge and it's lake.

4.99 out of 5 average rating, 203 reviews

A charming black cottage nestled among tall trees is visible. The entrance features a small deck with steps leading to the door. A kayak rests on the ground nearby, and seating areas can be seen on the gravel pathway, surrounded by lush greenery.

Tiny home in Tracy City

2BR Nature Getaway in Tiny Home w/ Lake access

Nature's Nook is a charming two-bedroom cottage. Combining nature with cutting-edge design draws inspiration from all over. Providing a fairytale experience with a cozy interior amidst towering trees. Nature's Nook embraces the beauty of nature with the inside scent of a campfire-lit night to birds singing good morning. This provides the ideal getaway to relax but still includes hiking and adventure. Nature is calling you at the Nook. . . Follow us on our socials @NaturesNookTN

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.

4.89 out of 5 average rating, 123 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.

4.94 out of 5 average rating, 184 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.

A charming farmhouse is set against a backdrop of open green space, featuring a covered front porch and large windows that provide natural light. The exterior is highlighted by a green metal roof and white siding, creating a welcoming presence in a serene rural setting.

4.81 out of 5 average rating, 135 reviews

Spacious 4BR/3BA Home Near Tims Ford Lake

Welcome to your beautifully renovated 1940s 4-bedroom, 3-bathroom vacation home near Tims Ford Lake! This spacious historic retreat comfortably sleeps 8 and offers everything you need for a relaxing getaway in Winchester, TN. Enjoy fast Wi-Fi, a Roku Smart TV, and a large private yard perfect for watching the sunrise from the back porch and sunset from the front. Large bedrooms, a cozy reading nook, and a spacious kitchen and living area awaits you!

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.

4.93 out of 5 average rating, 133 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.

4.98 out of 5 average rating, 219 reviews

The exterior of a modern cabin is showcased at sunset, featuring a metal roof and large windows. The structure is surrounded by greenery and dramatic rock formations, with warm lights illuminating the porch area, creating a welcoming ambiance facing the Tennessee River and mountain views.

Home in Chattanooga

Our Catty Shack

Oliver and Lacey (the cats) would love to welcome you to Our Catty Shack! ***NOTE: Our Catty Shack comes WITH CATS*** 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.

Popular amenities for Winchester pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

5 out of 5 average rating, 99 reviews

A modern two-story house features a green exterior with white trim and a welcoming porch. An American flag hangs from the porch, and soft outdoor lighting illuminates the entrance. A driveway leads to a garage, with trees providing a natural backdrop.

Home in Tullahoma

Lakeside Retreat at The Reserve w/ Golf Cart

A serene view of a house positioned beside a still pond, surrounded by tall, bare trees. The wooden structure features a sloping roof and large covered porches. The reflection of the house and trees in the water creates a peaceful scene, showcasing the natural setting.

5 out of 5 average rating, 28 reviews

Whitetail Creek Lodge Close to Campus

4.79 out of 5 average rating, 166 reviews

The home features a welcoming facade with a covered front porch and a rocking chair. Warm light emanates from the windows, highlighting the inviting space. A grassy area surrounds the home, providing a serene outdoor setting.

Home in Dunlap

The Cozy Little House

4.99 out of 5 average rating, 137 reviews

The dining area features a spacious table with elegant white chairs, set for six. Above, a sparkling chandelier illuminates the space, complementing the dark blue curtains. The open kitchen is visible in the background, showcasing modern appliances and ample counter space.

Home in Lookout Mountain

Dog/Family Friendly Mountain Gem near Attractions

4.96 out of 5 average rating, 337 reviews

The exterior of the home displays modern house numbers in black, affixed beside a pale blue front door. A potted plant with colorful flowers adds a welcoming touch to the entryway, while a light fixture hangs above.

Home in Lookout Valley

Chattanooga - The Isbill House

A spacious living area features large windows that let in natural light and provide views of the surrounding trees. A comfortable dark leather sofa is arranged with a rustic wooden coffee table. A wooden rocking chair adds to the cozy atmosphere, beside a staircase made of light-colored wood.

4.9 out of 5 average rating, 191 reviews

Return Guest House and Writers’ Retreat

4.95 out of 5 average rating, 474 reviews

A charming modern-rustic home is shown with a vibrant green front door. The exterior features a combination of dark blue and gray siding. A porch with two chairs and a walkway leads to the entrance. Surrounding greenery adds to the inviting atmosphere.

Home in Lookout Valley

Star Cottage 2

4.99 out of 5 average rating, 68 reviews

A modern blue cottage features a gabled roof and crisp white trim. The entryway is framed by two hanging planters, with an American flag displayed at the front. A well-maintained lawn surrounds the pathway leading to the door.

Home in Tullahoma

Beautiful cottage next to Tims Ford Lake

Pet-friendly home rentals with a pool

The exterior of a modern two-story cottage is presented, featuring a blue wooden facade and stone accents. A well-maintained lawn leads to the front door, while a two-car garage is visible. Clear skies and neighboring homes are seen in the background.

5 out of 5 average rating, 8 reviews

Barefoot Breeze

4.96 out of 5 average rating, 24 reviews

An infinity pool is visible on a wooden deck, offering expansive views of lush greenery and rolling hills under a colorful sky. The scene evokes a sense of serenity with trees surrounding the area, complementing the natural landscape.

Home in Trenton

Firefly Mountain- Newly Remodeled

5 out of 5 average rating, 11 reviews

A warm and inviting living area is highlighted by a stone fireplace, crackling with fire. Two plush armchairs and a spacious sectional sofa surround a textured coffee table. A festive Christmas tree adds a holiday touch, while large windows allow natural light to fill the space.

Home in Monteagle

Lakefront, 3 Fireplaces + Pizza Oven, Gorgeous!

4.97 out of 5 average rating, 118 reviews

An outdoor area features a large swimming pool surrounded by a spacious wooden deck, complemented by a five-person hot tub nearby. Lush greenery and flowering plants enhance the serene mountain views in the background.

Cabin in Dunlap

Heaven’s View Lodge, Pool, Pet Friendly

A modern house with a striking dark exterior stands against a colorful sunset. The façade features large windows framed by light trim, with a prominent gabled entrance. The surrounding yard is well-maintained, and a glimpse of the lake is visible in the background.

4.93 out of 5 average rating, 61 reviews

Basecamp Retreat TimsFordLake

4.85 out of 5 average rating, 123 reviews

An open-concept main floor features wooden walls and ceiling, creating a warm ambiance. A seating area with a brown sofa and coffee table is visible, alongside a dining space with a light-colored table and chairs. A staircase leads to the upper level, while a kitchen area includes stainless steel appliances.

Cabin in Bryant

Cloud 9 Cabin with an indoor pool, hot tub, & fire

A charming home with a light-colored exterior is set amidst lush greenery. A spacious deck with seating options faces a stone patio surrounded by vibrant foliage, creating an inviting outdoor area. Large windows provide ample natural light, enhancing the connection to the surrounding nature.

4.86 out of 5 average rating, 36 reviews

Forest Retreat: Poolside Bliss Close to Campus

A contemporary two-story home showcases a light-colored exterior with a gabled roof and a covered front porch. A balcony extends from the upper level, complemented by a ceiling fan. The landscaped area features low shrubbery and a paved pathway leading to the entrance.

5 out of 5 average rating, 35 reviews

The Modern Mainstay at Barefoot Bay

Private, pet-friendly home rentals

A metal dock extends over the calm water, leading to a covered boat slip with seating options. Surrounding greenery is visible in the distance, contributing to the tranquil lakeside setting. The sky appears clear and blue, enhancing the serene atmosphere.

5 out of 5 average rating, 18 reviews

Sunset Cottage +Dock on Tims Ford Sleeps 12

4.9 out of 5 average rating, 10 reviews

Cabin in Monteagle

Everly House in Deer Lick Falls

4.75 out of 5 average rating, 28 reviews

A spacious studio suite is showcased, combining modern and rustic elements. A large king-sized bed is positioned against a neutral wall, complemented by a leather sofa and a wooden dining table. Natural light floods the area, enhanced by soft lighting fixtures.

Flat in Monteagle

Studio in Monteagle - Mins from the Caverns

4.98 out of 5 average rating, 252 reviews

The exterior of the recently remodeled farmhouse is presented, featuring a blue color scheme and a covered porch. Lush greenery surrounds the home, with flower beds accentuating the landscape. A small tree with vibrant red leaves is visible near the entrance.

Cottage in Fayetteville

Country Cottage Hideaway near Lynchburg

Campervan/Motorhome in Winchester

An RV is parked on a gravel site in a wooded area, surrounded by trees. A picnic table and two chairs are positioned nearby on a concrete surface. Additional RV units are visible in the background, offering a sense of community.

4.8 out of 5 average rating, 10 reviews

Happy Campers

5 out of 5 average rating, 46 reviews

On Water w/ Private Dock, Entire Home, sleeps 14

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.

5 out of 5 average rating, 23 reviews

Lakeside Serenity: Cove Retreat