
Pet-friendly vacation rentals in Winchester
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Top-rated pet-friendly home rentals in Winchester
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Popular amenities for Winchester pet-friendly home rentals
Pet-friendly house rentals

Dog/Family Friendly Mountain Gem near Attractions
We had such a great stay here. Easily the most responsive and helpful hosts we’ve ever encountered. Highly recommend!

Mountain Dale Retreat
We stayed here for my son’s graduation and it was perfect! We were able to bring our dogs and the home was perfect for hosting family and relaxing with a cup of coffee and taking in the beautiful Mountain view. The home has everything you could possibly ask for- the kitchen is fully stocked with literally everything you could want and more. We will book this home again for our next son’s graduation! Perfect stay!

Chattanooga - The Isbill House
Really cute house, super clean, cozy bed. Had everything covered for a comfortable stay, and we enjoyed it! Also very convenient to some great options for food.

Return Guest House and Writers’ Retreat
This is a lovely, peaceful place. Our group was two adult couples. We had a couple of birders and they were excited about the visit. We all enjoyed being close to Sewanee, local restaurants, and Mooney's Emporium.

Relax & Unwind in Cozy Farm Stay 7 mins from I-24
Thank you so much to Emily. We had a great week, a delightfully comfortable stay, quiet and safe surroundings. We felt right at home. Emily even went out of the way to order a coffee grinder before we arrived.

Stay ON a Waterfall—13 acres! Bluffs, deck, views!
Excellent host and home! Absolutely beautiful inside and out! My main love was the swinging bed! 2 nights spent and it was the best sleep ever!! Only thing I wish this property had was a hottub! The back decks are incredible, they would be even better with a hottub. Overall, a 5 out of 5 stars!!

Star Cottage 2
The house was within 15-20min to all activities including the zoo, aquarium, looking out mountain, rock city, and several hiking opportunities. All kitchen essentials seemed to be provided, and the house was well kept. April was also very responsive and checked in on us during a big storm that came through.

Beautiful cottage next to Tims Ford Lake
Great place to stay, good location and beautiful house.
Pet-friendly home rentals with a pool

Barefoot Breeze
Beautiful place we enjoyed our stay would love to come back if we are back in town.

Twin Creeks Getaway, Pet Friendly!
We have stayed here twice and it was great both times. We feel right at home. We love sitting on the front upstairs porch in the mornings and evenings. The inside is very nice and comfortable and has everything we need. It's a great location to walk down to the marina for lunch or dinner and to rent a boat. However, it is far enough away that you don't feel crowded by the busyness of the marina.

Heaven’s View Lodge, Pool, Pet Friendly
Heaven’s View Lodge is a beautiful cabin. The views are absolutely stunning. The cabin is well stocked, clean, modern and beautiful. The pool and hot tub were a wonderful addition, as was the fire pit. Nicely accommodates multi families traveling together. It was conveniently close to town but felt remote and private which was great. The hosts were wonderful. Definitely would recommend a stay at Heaven’s View!

Pool, Huge Backyard - Near Hiking & The Caverns
House was beautiful! Kevin was super accommodating & quick in responding to any questions we had. Would definitely recommend!

Basecamp Retreat TimsFordLake
This home was beautiful and comfortable. Perfectly fitted with everything you need and more! The greened in back porch was heaven. The only tiny thing- I wish I had read closer bc while the house was on the lake, you don’t have direct access to walk to the water from the yard as I originally thought. By no means did it ruin the stay, that would have just made it absolutely perfect. Wonderful house, very easy to deal with and helpful owner, definitely recommend!!

Quail Run Farm: Pool Home, 15 Mins to Chattanooga
Great stay near Chattanooga! We arrived at night then in the morning loved getting to look around the beautiful property. Would definitely recommend!

Forest Retreat: Poolside Bliss Close to Campus
A lovely stay, beautiful, peaceful, perfect

The Modern Mainstay at Barefoot Bay
We really enjoyed Korina’s place. It was spotlessly clean and stocked with everything you may need. Beautiful private neighborhood sitting on the lake. Korina was a great accommodating host. Recommend it highly!
Private, pet-friendly home rentals

Summer Sewanee Lake House
This location is very private and quiet. Exactly what I was seeking. The home provides a cozy yet pleasing respite from City, Enviromental and Human distractions. The is a GEM and you will be blessed if you are called to experience the stillness of this unique space and place. I look forward to returning.

Bluebird Rest- Peaceful Lake Retreat
Bluebird was a little slice of heaven. The amazing screen porch was our favorite place. We loved relaxing, listening to the sounds of nature and looking at the lake. We slept like a baby on the comfortable beds. The shower was great too, never ran out of hot water and great water pressure. We will definitely be back to this little gem. Shellia was a great host!

Fireside Cabin on the Bluff
Fiancé an I wanted a private get away, had eveything we needed, amazing view, nice to wake up to the birds chirping.

Tims Ford Lake Retreat - The Got-Away
Cynthia’s place was spotless, with comfy beds and plenty of room for our group of eight, including five teens. It was perfect for relaxing during our two-day golf tourney at Bear Trace in Tim Ford Park. We especially loved the Colorado room for morning coffee. Great space to unwind and hang out!

The Cottage at Tim's Ford Lake (Sleeps 10)
Beautiful, cozy home in a nice, safe and well-kept neighborhood. Beautiful surroundings, that brings such a sense of peace! Kim was an amazing host. She was very friendly, accommodating and quick to respond. We will definitely be back on our next vacation!

Clementine Cottage
The Clementine Cottage was perfect. It was cute, quaint, CLEAN, well outfitted with lots of nice extras. She had brochures on all the nearby activities. We fished, we kayaked, we sat around the fire pit, we enjoyed the screened porch. My only complaint would be that I mistakenly thought the cabin would be a little more secluded but even with that being said, it was quiet, it was serene, we enjoyed our long weekend very much and are talking about another trip there. And Gloria is a great hostess. We were pleasantly surprised at how nice everything was.

“The Country” Lake House w/ Private Dock
This home was fantastic. We really appreciated the baby gear including safety gates, and the air hockey and football tables downstairs. The kitchen was well-equipped to cook for our crew of 7

AquaHallics Retreat 2
Veronica was great to work with, quick to respond and helpful with any questions. They have thought of everything in the house. From extra flip flops and a first aid kit to bath robes and bug spray they had it all covered. Would definitely stay there again.
Quick stats about vacation rentals that are pet-friendly in Winchester
Total rentals
30 properties
Nightly prices starting at
G$12,548 GYD before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
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- Tennessee Aquarium
- Cloudland Canyon State Park
- Monte Sano State Park
- Sweetens Cove Golf Club
- Black Creek Club
- Chattanooga Golf and Country Club
- Chattanooga Choo Choo
- The Ledges
- Coolidge Park
- Creative Discovery Museum
- The Lookout Mountain Club
- Old Fort Golf Course
- Kyujo-mae Station
- Hunter Museum of American Art
- National Medal of Honor Heritage Center