Pet-friendly holiday rentals in Winchester

4.98 out of 5 average rating, 141 reviews

The Gipson House, established in 1930, features a charming white exterior and welcoming porch. Lush green plants hang by the entryway, while two bicycles are parked on the lawn, reflecting a peaceful rural setting bathed in sunlight.

Cottage in Pelham

The Historic Gipson House Caverns Friendly !

140 guests, 140 five star reviews! This is an historic house. Completely remodeled with modern convenances. Book now for 2026 caverns dates ! Top shelf accommodations ?You’ve found them ! See our reviews ! Guests love the Gipson House ! Private home and property ! Caverns 4 miles/10 mins away. Circa 1930, beautifully appointed Gipson House in scenic Pelham Valley between Chattanooga/Nashville, area has world class hiking , also near Sewanee Recognized super host and guest favorite

5.0 out of 5 average rating, 109 reviews

A shipping container home is surrounded by lush trees, featuring large windows that offer views of the forest. Natural light filters in, illuminating the interior space, which is thoughtfully designed to blend with the outdoor scenery.

Treehouse in Sewanee

Private Treehouse Retreat! Sauna|Hot Tub|Pool

Imagine sipping your coffee while watching the deer pass through 5 acres of forest from our steam sauna. Imagine enjoying a private marked path on property or hopping in your car to hike a 9 mile, 5 hour trail just 15 min from home, then recovering in the hot tub. If you want a private city escape, our shipping container treehouse is for you! PRIVACY NOTE: There are ZERO shared spaces, no on else on property. While we live in a 'neighborhood' you cannot see another home from our treehouse.

4.94 out of 5 average rating, 294 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.

4.97 out of 5 average rating, 128 reviews

Home in Monteagle

Stayframe: a designer getaway with mountain views

Welcome to my custom-built Aframe in the forest just 90 mins from Nashville. This quiet retreat perched on the Cumberland Plateau was recently featured in Travel + Leisure and gives you access to the hikes and waterfalls the area is known for, while offering an elevated experience. Enjoy the soaking tub, gas fireplace, fast wifi, Smart TV, well-appointed kitchen, and bluff views. Sewanee University, Cumberland Caverns, Fiery Gizzard, and Sweetens Cove are all within a short drive.

Cabin in Lynchburg, Moore County

A view from the porch reveals the serene waters of Tims Ford Lake, bordered by lush greenery. The railing is partially visible, with sunlight filtering through the trees, creating dappled shadows on the deck. A bird feeder hangs nearby, inviting wildlife.

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.

4.97 out of 5 average rating, 237 reviews

5.0 out of 5 average rating, 109 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

Beautiful lakeside home on Tim's Ford Lake! Short Walk or Golf Cart ride to Blue Gill Grill & Holiday Landing Marina. Boat Parking on the Driveway during your stay! First Floor: Master Bed with Full Bath, Dining Room, Living Room, Kitchen (Fully stocked with basic spices and cooking utensils). Outside Patio with Fire Place and seating. Second Floor: BR 2- King Bed. BR 3 Queen Bed, Loft Space, Sectional Couch, Pull out Queen. *No Smoking *Max 10 Guest *Front Door Security Cam*

4.98 out of 5 average rating, 245 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.

4.9 out of 5 average rating, 134 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.

Home in Lynchburg, Moore County

A welcoming front porch features multiple wooden rocking chairs arranged neatly along the covered area, with a central entryway leading to the home. The porch is framed by wooden beams and offers a view of the expansive lawn and nearby structures.

TN Fire 3 bedroom 2 bath beautiful new home

Beautiful 3BR/2bath new barndominium. Walking distance to Historic Lynchburg town square & Jack Daniel's distillery. BR1 Queen bed/private bath, BR2 Queen bed, BR 3 Queen bed, Queen sofa sleeper in LR. 2 Full Baths in home with walk in showers. Full kitchen and washer/dryer. Free/fast wifi & Smart TV. Nice comfortable stay for up to 8 people. Pavilion with barbecue, picnic tables, fire pit. Large side yard, pets must be approved (limit 2, 25 lbs. maximum, $30 pet fee).

4.96 out of 5 average rating, 230 reviews

4.89 out of 5 average rating, 495 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. Hot tub and Tuft & Needle mattresses. Basic amenities provided. Includes Wi-Fi and DVD player.

4.95 out of 5 average rating, 225 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.

4.99 out of 5 average rating, 115 reviews

Tiny home in Tracy City

Nature lovers dream retreat/the Square Root

Discover, modern comfort and convenience at the Square Root. Situated in a prime location, this short-term, rental property offers a stylish retreat with all the essential amenities. Experience the perfect blend of relaxation and adventure, surrounded by restaurants, shops, and attractions. Unwind in our well-appointed rooms, enjoy the on-site amenities, and indulge in the vibrant local scene. Your ideal getaway awaits you at the Square Root.

Popular amenities for Winchester pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.98 out of 5 average rating, 130 reviews

Home in Tracy City

Little Green Cottage

4.93 out of 5 average rating, 144 reviews

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.

Home in Sewanee

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

Home in Lynchburg, Moore County

A comfortable living room is presented, featuring a light-colored leather sectional sofa. A textured blue and gray area rug anchors the space. A decorative ottoman with a small plant on top adds a touch of nature. Natural light enters through window treatments, enhancing the room's warmth.

Sunshine’s house, walk to JD, pets welcome

4.98 out of 5 average rating, 100 reviews

4.89 out of 5 average rating, 102 reviews

The exterior of a Victorian farmhouse is showcased, featuring a white facade with green shutters and a distinctive red metal roof. A white picket fence surrounds the house, complemented by a gravel driveway and well-maintained landscaping, with trees in the background.

Home in Whitwell

1900 Farmhouse, Spa Bath, 2 King Masters, Firepit

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.

5.0 out of 5 average rating, 42 reviews

Sunset Cottage +Dock on Tims Ford Sleeps 12

The entrance features a wooden door with multiple glass panels, complemented by a dark brown welcome mat and a tall, rustic sign that reads 'WELCOME.' The porch is framed by vertical siding and surrounded by greenery.

4.98 out of 5 average rating, 43 reviews

A quiet getaway.

5.0 out of 5 average rating, 61 reviews

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

The front entrance of the cottage features a welcoming green door framed by white siding and a covered porch. A potted plant adds a touch of greenery beside the entrance, and a stone pathway leads to the door, inviting guests inside.

4.88 out of 5 average rating, 52 reviews

Cottage on Cedar

Pet-friendly home rentals with a pool

4.99 out of 5 average rating, 105 reviews

A spacious timber frame home is situated on a hillside overlooking a lush valley, with mist rising from the trees. A pool is positioned near the house, surrounded by a manicured lawn. The outdoor area includes a fire pit, enhancing the tranquil atmosphere.

Home in South Pittsburg

Cozy Cabin in the Clouds

4.95 out of 5 average rating, 74 reviews

Basecamp Retreat TimsFordLake

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.

5.0 out of 5 average rating, 51 reviews

The Modern Mainstay at Barefoot Bay

Two kayaks in vibrant orange and blue are positioned on a concrete patio, adjacent to a green lawn. Trees with budding leaves and flowering branches frame the serene lakeside view. A covered deck above provides shade, enhancing the inviting outdoor space.

4.88 out of 5 average rating, 50 reviews

Luxurious New Build LakeHouse Tim’s Ford 4BR4Bath

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.

5.0 out of 5 average rating, 25 reviews

Barefoot Breeze

4.82 out of 5 average rating, 62 reviews

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.

Home in Sewanee

Forest Retreat: Poolside Bliss Close to Campus

4.86 out of 5 average rating, 14 reviews

By the pool

5.0 out of 5 average rating, 7 reviews

4-bedroom Lake house in Twin Creeks Winchester TN

Private, pet-friendly home rentals

Guest house in Lynchburg, Moore County

The exterior of the guest house is visible, featuring a covered porch with two chairs positioned on a stone patio. The grey siding contrasts with the wooden beams and red metal roof, while a driveway and a fenced yard can be seen in the background.

Country Guest House

4.96 out of 5 average rating, 327 reviews

4.97 out of 5 average rating, 631 reviews

A charming cabin with a green metal roof is situated on a grassy hillside. Surrounding trees frame the view, while steps lead from the driveway to the entrance. The cabin overlooks the valley, providing a scenic backdrop of rolling hills in the distance.

Cabin in Altamont

Sunrise Mountain Cabin

4.88 out of 5 average rating, 317 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

4.94 out of 5 average rating, 16 reviews

The modern kitchen is equipped with stainless steel appliances, including an oven and microwave. Black cabinetry contrasts with white countertops, while decorative wall art and plants add character. Natural light filters through a window, illuminating the space's unique backsplash design.

Cottage in Winchester

Waterside Cottage #12 Pet-Friendly & Marina Slip

5.0 out of 5 average rating, 32 reviews

An inviting entryway features a blue door leading to an open living space illuminated by natural light. A ceiling fan hangs above a spacious seating area with a light-colored sectional couch and a coffee table. Greenery is displayed in modern wall-mounted planters.

Cottage in Tullahoma

Tranquility @ The Reserve-Holiday Landing

4.99 out of 5 average rating, 90 reviews

A charming house features a light-colored exterior with dark shutters and a welcoming front porch. The surrounding landscape includes bare trees and gentle foliage, highlighting the home’s spacious driveway leading up to the entrance.

Cottage in Tullahoma

Tims Ford Lake Retreat - The Got-Away

4.98 out of 5 average rating, 59 reviews

Home in Sewanee

Whitetail Creek Lodge Close to Campus