
Pet-friendly holiday rentals in Winchester
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Top-rated pet-friendly home rentals in Winchester
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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.

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.

Waterfall Log Cabin
Cozy Log Cabin just feet away from the top of our 2 magnificent private waterfalls. The Falls at Sewanee Creek is located in America’s most biodiverse area on Tennessee's Eco-Rich Cumberland Plateau. Walk to the observation bench at the top of the biggest 50 ft waterfall. Follow the trail behind the falls. Adventure awaits on a rugged, bouldering hike, past cascades and the second big waterfall to two private caves. Disclaimer: Flow of all Waterfalls is subject to weather fluctuations.

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.

Little Green Cottage
Relax & unwind where mother nature meets modern nature at the Little Green Cottage. Each space is thoughtfully designed for a comfortable & luxurious stay. Enjoy an open layout w/ vaulted ceilings & natural earth-tone features, a full functioning kitchen & dining area, bedrooms w/ king size beds that each come with their own attached bathroom & a large screen porch w/ a view that will take your breath away. All the fun, recreational activities are right outside your door! Dog friendly!

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.

Mac's Lodge Tiny Home
FEATURES A HOT TUB! Relax in style at Mac's Lodge (formerly listed as The Seashore), 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

Come Stay & Play at the farm
10% discount for stays 3+ days, no cleaning fees, no pet deposit. Escape to the peaceful hills of Little Tail Farms! This pet-friendly, one-bedroom apartment sits above a detached garage and offers sweeping views of our barnyards—home to goats, sheep, alpacas, mini horses, and livestock guardian dogs. Wander the pastures, enjoy animal interactions (treats fed outside the fence, please!), and experience a cozy stay rooted in nature, charm, and a touch of farm magic.

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.

Lovely Lake View Home at Twin Creeks Marina
This Craftsman-style, lake-view house is located in the private, gated lakeside community of Twin Creeks Village at scenic Tim's Ford Lake in Winchester, TN. It features an open floor plan with 4 bedrooms, 3 baths, game room, screened porch and huge deck overlooking the lake. Use the included golf cart to go to the swimming pools, marina, bar & grill or on-site convenience store. Information on boat & jet ski rentals are available at the marina shop.
Popular amenities for Winchester pet-friendly home rentals
Pet-friendly house rentals

Summer Sewanee Lakehouse

The Sewanee House: Serene Oasis close to Campus

Whitetail Creek Lodge Close to Campus

Mama Bear’s Woodland Escape

Riverfront Oasis 15 Min to Downtown Chattanooga

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

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

Lakeside Serenity: Cove Retreat
Pet-friendly home rentals with a pool

Barefoot Breeze

Twin Creeks Getaway, Pet Friendly!

Lakefront, 3 Fireplaces + Pizza Oven, Gorgeous!

Basecamp Retreat TimsFordLake

Forest Retreat: Poolside Bliss Close to Campus

The Modern Mainstay at Barefoot Bay

5 Acres! Cozy Nature Retreat

Gorgeous lake home in Twin Creeks with Lake View
Private, pet-friendly home rentals

Fireside Cabin on the Bluff

Endless View - Crisp & Cozy Lower Cottage

Sweet Retreat-across from Twin Creeks Marina

Tims Ford Lake Retreat - The Got-Away

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 | $312 NZD | $329 NZD | $335 NZD | $333 NZD | $473 NZD | $454 NZD | $447 NZD | $415 NZD | $324 NZD | $350 NZD | $350 NZD | $361 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 | 
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 $123 NZD per night before taxes and fees

Verified guest reviews
Over 1,350 verified reviews to help you choose

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

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Winchester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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 kayak Winchester
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 - Pet-friendly rentals Franklin County
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 - Pet-friendly rentals United States
 
- Tennessee Aquarium
 - Cloudland Canyon State Park
 - Monte Sano State Park
 - Sweetens Cove Golf Club
 - Black Creek Club
 - The Ledges
 - Coolidge Park
 - The Lookout Mountain Club
 - Chattanooga Golf and Country Club
 - Chattanooga Choo Choo
 - Old Fort Golf Course
 - Creative Discovery Museum
 - Hunter Museum of American Art
 - National Medal of Honor Heritage Center