
Pet-friendly holiday rentals in Winchester
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Winchester
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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)

The Historic Gipson House Caverns Friendly!
127 guests, 127 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

Charming Retreat 5 Min to Tims Ford Lake; Sleeps 8
Welcome to your beautifully renovated 1940s historic home in Winchester, Tennessee, just 5 minutes from Tims Ford Lake. This spacious 4-bedroom, 3-bath vacation home comfortably sleeps 8. Guests will appreciate fast Wi-Fi, a Roku Smart TV, and large comfortable bedrooms. Perfect for: • Family vacations and reunions • Boating and fishing trips at Tims Ford Lake • Couples or friends’ weekend getaways • Exploring historic Winchester • Quiet countryside retreats with beautiful sunrises and sunsets

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.

Stayframe: a designer getaway with mountain views
Welcome to our custom-built Aframe in the woods just 90 minutes from Nashville. This quiet retreat perched on the Cumberland Plateau gives you access to the hikes and waterfalls the area is known for, while offering an elevated guest 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. Sorry, no parties, events, or photoshoots.

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.

Sunrise Mountain Cabin
Welcome to Sunrise Mt. Cabin is located on top of the Cumberland Plateau with a great view of the valley check out our 2 other cabins Patriot's Retreat & Sunrise Mtn Treeshouse. The cabin has approximately 1400 square feet and is fully furnished with full kitchen and more. Hiking trails and fishing pond only a short walk away. Several major state parks with hikes within a few miles of the cabin. The cabin has fiber optic WiFi which is not shared. Pet cats not allowed; we are allergic.

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.

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*

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

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.

The Mockingbird Tiny Home - Fire Pit Pet Friendly!
Welcome to The Mockingbird - your cozy retreat in the peaceful Water’s Edge community of Tracy City, TN, just minutes from Monteagle and Sewanee. Perfectly tucked into the South Cumberland Plateau, this area offers the best of both worlds: endless outdoor adventure and small-town charm with great restaurants and unique shopping nearby. Inside, The Mockingbird invites you to slow down and savor Southern charm with high ceilings, abundant natural light, and classic decor.
Popular amenities for Winchester pet-friendly home rentals
Pet-friendly house rentals

Sunset Ridge | Historic Monteagle Hiking

The Sewanee House: Main House + Guest Wing

Whitetail Creek Lodge Close to Campus

Lake Life

Riverfront Oasis 15 Min to Downtown Chattanooga

Spacious 4 bedroom 2 bath house king bed in master

2-Acre Tim's Ford Lake House (11 Beds + Full Gym)

Relax & Unwind in Cozy Farm Stay 7 mins from I-24
Pet-friendly home rentals with a pool

Barefoot Breeze

Lakefront, 3 Boats + Pizza Oven, Gorgeous!

Firefly Mountain- Newly Remodeled

Pool, Spa, 2 Kitchens, 5 Baths, 15m to Chatt!

Basecamp Retreat TimsFordLake

Forest Retreat: Poolside Bliss Close to Campus

The Modern Mainstay at Barefoot Bay

5 Acres! Cozy Nature Retreat
Private, pet-friendly home rentals

Historic Farmhouse, convenient location!

Endless View - Crisp & Cozy Lower Cottage

Tims Ford Lake Retreat - The Got-Away

Happy Campers

Lakefront Tiny Home/Pet Friendly/ Private Dock

Nature lovers dream retreat/the Square Root

Flat Branch Lodge - Tracy City, TN

AquaHallics Retreat 2
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £134 | £141 | £144 | £143 | £203 | £195 | £192 | £192 | £150 | £149 | £132 | £129 |
| Avg. temp | 5°C | 8°C | 12°C | 17°C | 21°C | 25°C | 27°C | 27°C | 23°C | 17°C | 11°C | 7°C |
Quick stats about holiday rentals that are pet-friendly in Winchester

Total holiday rentals
Explore 40 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at £38 per night before taxes and fees

Verified guest reviews
Over 1,410 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Winchester holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winchester rentals

4.9 Average rating
Winchester stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a firepit Winchester
- Rentals with a patio Winchester
- Rentals with lake access Winchester
- Family-friendly rentals Winchester
- Rentals with pools Winchester
- Cabin rentals Winchester
- Rentals with a fireplace Winchester
- Rentals with a kayak Winchester
- Rentals with outdoor seating Winchester
- Rentals with a washing machine and dryer Winchester
- House rentals Winchester
- Pet-friendly rentals Franklin County
- Pet-friendly rentals Tennessee
- Pet-friendly rentals United States
- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Coolidge Park
- Chattanooga Choo Choo
- Rock City
- Hunter Museum of American Art
- Creative Discovery Museum
- South Cumberland State Park
- Raccoon Mountain Caverns & Campground
- Dublin Park
- Point Park
- Chattanooga Zoo
- Cathedral Caverns State Park
- U.S. Space & Rocket Center
- Cumberland Caverns
- Chattanooga Whiskey Experimental Distillery
- Old Stone Fort State Archaeological Park
- Huntsville Botanical Garden
- Burritt on the Mountain
- Finley Stadium
- Short Mountain Distillery
- Discovery Center
- Lowe Mill Arts And Entertainment




