
Pet-friendly vacation 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

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*

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.

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 Wool Attic at Summer Fields
This farm stay is in half of a renovated garage on our working sheep farm. Enjoy the sheep, livestock guardian dogs, and slower pace, while still being close to area attractions. It has an open downstairs with a full kitchen, bathroom, dining area, pool table, and porch. Sleeping areas, upstairs in the attic, or in our sleeping loft are too short for standing but otherwise cozy for sleeping. Farm workers will be doing chores and interacting with the animals during your stay.

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.
Popular amenities for Winchester pet-friendly home rentals
Pet-friendly house rentals

Sunset Ridge | Historic Monteagle Hiking

Paddle Inn

Whitetail Creek Lodge Close to Campus

Lake Life

Spacious 4 bedroom 2 bath house king bed in master

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

Rooster's Roost of Bells Cove - 15 Minutes from th

Stay ON a Waterfall—13 acres! Bluffs, deck, views!
Pet-friendly home rentals with a pool

Barefoot Breeze

Lakefront, 3 Boats + Pizza Oven, Gorgeous!

Pool, Huge Backyard - Near Hiking & The Caverns

Basecamp Retreat TimsFordLake

Luxury lake home with amenities near Sewanee

Forest Retreat: Poolside Bliss Close to Campus

The Modern Mainstay at Barefoot Bay

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

Bluebird Rest- Peaceful Lake Retreat

Historic Farmhouse, convenient location!

Tims Ford Lake Retreat - The Got-Away

Waterfront Cottage #7 - PET Friendly & Free Boat!

Tranquility @ The Reserve-Holiday Landing

Happy Campers

Nature lovers dream retreat/the Square Root

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 | ﺩ.ﺇ654 | ﺩ.ﺇ690 | ﺩ.ﺇ701 | ﺩ.ﺇ698 | ﺩ.ﺇ992 | ﺩ.ﺇ951 | ﺩ.ﺇ940 | ﺩ.ﺇ936 | ﺩ.ﺇ735 | ﺩ.ﺇ727 | ﺩ.ﺇ643 | ﺩ.ﺇ632 |
| 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 vacation rentals that are pet-friendly in Winchester

Total vacation rentals
Explore 40 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

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

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Winchester vacation rentals include wi-fi 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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- 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
- Rock City
- Chattanooga Choo Choo
- Hunter Museum of American Art
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- Chattanooga Zoo
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