
Pet-friendly holiday rentals in Winchester
Find and book unique pet-friendly homes on Airbnb
Quick stats about holiday rentals that are pet-friendly in Winchester

Total holiday rentals
Explore 30 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $17 NZD per night before taxes and fees

Verified guest reviews
Over 1,530 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Winchester holiday 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!
Top-rated pet-friendly home rentals in Winchester
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

The Historic Gipson House Caverns Fav !
135 guests, 135 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

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)

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.

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).

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.

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.

Tennessee Mountain House
This one bedroom remote cabin is located on the Cumberland Plateau between Monteagle & McMinnville in the National historic district of Beersheba Springs. Three acres of wooded bluff property overlooks Savage Gulf & provides a secluded, quiet getaway. sleeps 4 but suitable for mostly 2 guest. Also, as you will note: this is the guest house which FACES the SIDE of the main house, so please use the main house porch for sitting and enjoying the view as well.
Popular amenities for Winchester pet-friendly home rentals
Pet-friendly house rentals

Sunset Cottage +Dock on Tims Ford Sleeps 12

Fireside House 2

The Sewanee House: Main House + Guest Wing

Whitetail Creek Lodge Close to Campus

Little Green Cottage

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

“The Country” Lake House w/ Private Dock

A-Frame on Tims Ford Lake Private Boat Dock w/slip
Pet-friendly home rentals with a pool

Barefoot Breeze

Lakefront, 3 Boats + Pizza Oven, Gorgeous!

Pool, Huge Backyard - Near Hiking & The Caverns

Exquisite TN Farmland Getaway

Basecamp Retreat TimsFordLake

Forest Retreat: Poolside Bliss Close to Campus

The Modern Mainstay at Barefoot Bay

4-bedroom Lake house in Twin Creeks Winchester TN
Private, pet-friendly home rentals

Spring Sewanee Lakehouse

Lake Life

Tims Ford Lake Retreat - The Got-Away

Waterfront Cottage #7 - PET Friendly & Free Boat!

Tranquility @ The Reserve-Holiday Landing

Lakeside Cottage Retreat at Tim's Ford Lake

The Cottage at Tim's Ford Lake (Sleeps 10)

Lakefront Tiny Home/Pet Friendly/ Private Dock
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $309 NZD | $291 NZD | $271 NZD | $330 NZD | $468 NZD | $449 NZD | $444 NZD | $442 NZD | $347 NZD | $344 NZD | $304 NZD | $298 NZD |
| 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 |
Destinations to explore
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- Rentals with lake access Winchester
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- Cabin rentals Winchester
- Rentals with a kayak Winchester
- Rentals with a washing machine and dryer Winchester
- Family-friendly rentals Winchester
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- Rentals with pools Winchester
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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
- Rock City
- Chattanooga Choo Choo
- Coolidge Park
- South Cumberland State Park
- Point Park
- Hunter Museum of American Art
- Von Braun Center, North Hall
- Raccoon Mountain Caverns & Campground
- Chattanooga Zoo
- Old Stone Fort State Archaeological Park
- Creative Discovery Museum
- U.S. Space & Rocket Center
- Huntsville Botanical Garden
- Lowe Mill Arts And Entertainment
- Cumberland Caverns
- Cathedral Caverns State Park
- Short Mountain Distillery
- Burritt on the Mountain
- Discovery Center
- Chattanooga Whiskey Experimental Distillery
- Barfield Crescent Park





