
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.

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)
WalkabilityPetsCleanliness

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.
Outdoor spacesPetsIndoor spaces

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.
PetsOutdoor spacesHospitality

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.
WalkabilityOutdoor spacesCondition

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.
PetsOutdoor spacesNearby

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.
Outdoor spacesGetting aroundHospitality

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.
PetsWalkabilityHiking

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*
PetsWalkabilityGetting around

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
PetsWalkabilityComfort

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.
PetsOutdoor spacesKitchen

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).
WalkabilityOutdoor spacesHospitality

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

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

Little Green Cottage
Outdoor spacesPetsCleanliness

Mulberry Cottage Guest House
WalkabilityPetsCheck-in

Fireside House 1
Outdoor spacesWalkabilityDecor

1900 Farmhouse, Spa Bath, 2 King Masters, Firepit
PetsOutdoor spacesCondition

Sunset Cottage +Dock on Tims Ford Sleeps 12
PetsOutdoor spacesCleanliness

A quiet getaway.
Outdoor spacesPetsBathroom

On Water w/ Private Dock, Entire Home, sleeps 14
Outdoor spacesWalkabilityBathroom
Pet-friendly home rentals with a pool

Cozy Cabin in the Clouds
PetsOutdoor spacesValue

Basecamp Retreat TimsFordLake
Outdoor spacesWalkabilityValue

The Modern Mainstay at Barefoot Bay
PetsWalkabilityAmenities

Luxurious New Build LakeHouse Tim’s Ford 4BR4Bath
Outdoor spacesLocationCondition

Barefoot Breeze
Outdoor spacesPetsLayout

Forest Retreat: Poolside Bliss Close to Campus
WalkabilityOutdoor spacesAmenities

By the pool
Outdoor spacesFamilyLocation

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

The Historic Gipson House Caverns Favorite
PetsOutdoor spacesView

Waterfront Cottage #7 PET & Wheelchair Friendly!
PetsViewBarbecue

Tranquility @ The Reserve-Holiday Landing
WalkabilityPetsAccuracy

A-Frame on Tims Ford Lake Private Boat Dock w/slip
Outdoor spacesPetsBarbecue

Lakeside Serenity: Cove Retreat
Outdoor spacesSleep qualityAmenities

Cozy Cottage on Tim's Ford Lake- The Holiday House
WalkabilityPetsLayout

Long Weekend
WalkabilityOutdoor spacesLocation

2-Acre Tim's Ford Lake House (11 Beds + Full Gym)
WalkabilityPetsLocation
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $299 NZD | $282 NZD | $262 NZD | $289 NZD | $413 NZD | $410 NZD | $430 NZD | $428 NZD | $336 NZD | $333 NZD | $294 NZD | $289 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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- 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
- Raccoon Mountain Caverns & Campground
- Chattanooga Zoo
- Von Braun Center, North Hall
- Old Stone Fort State Archaeological Park
- Creative Discovery Museum
- U.S. Space & Rocket Center
- Huntsville Botanical Garden
- Cumberland Caverns
- Cathedral Caverns State Park
- Lowe Mill Arts And Entertainment
- Burritt on the Mountain
- Discovery Center
- Chattanooga Whiskey Experimental Distillery
- Henry Horton State Park
- Barfield Crescent Park





