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

Total vacation rentals
Explore 30 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at $14 CAD per night before taxes and fees

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

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

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Winchester vacation 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!
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 !
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

Relax & Unwind in Cozy Farm Stay 7 mins from I-24
Come enjoy a cozy getaway in Sewanee! You’ll love this space because of the location, amenities, and cleanliness. This home is best suited for couples, small families and those traveling with pets. This mobile home has an open layout. It’s 700 square feet and sits near the woods, off a back road, bordering a horse pasture and trees. It has a spacious fenced-in yard. Located 7 minutes off I-24 for those driving thru, and a short walk or drive from Mountain Goat Trail if you want to walk or jog.

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.

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.

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.

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

Mulberry Cottage Guest House

Little Green Cottage

Fireside House 1

1900 Farmhouse, Spa Bath, 2 King Masters, Firepit

Sunset Cottage +Dock on Tims Ford Sleeps 12

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

A quiet getaway.

Cottage on Cedar
Pet-friendly home rentals with a pool

Cozy Cabin in the Clouds

Basecamp Retreat TimsFordLake

The Modern Mainstay at Barefoot Bay

Luxurious New Build LakeHouse Tim’s Ford 4BR4Bath

Barefoot Breeze

Forest Retreat: Poolside Bliss Close to Campus

By the pool

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

The Nest at The Retreat @ Deer Lick Falls

Waterfront Cottage #7 PET & Wheelchair Friendly!

Tranquility @ The Reserve-Holiday Landing

“Family Traditions” Cottage - 4-bed lake retreat

Lakeside Serenity: Cove Retreat

Long Weekend

Cascade Hollow Lodge

2-Acre Tim's Ford Lake House (11 Beds + Full Gym)
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $245 CAD | $232 CAD | $215 CAD | $237 CAD | $339 CAD | $336 CAD | $353 CAD | $352 CAD | $276 CAD | $273 CAD | $241 CAD | $237 CAD |
| 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 |
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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
- Cumberland Caverns
- U.S. Space & Rocket Center
- Huntsville Botanical Garden
- 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





