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Pet-friendly vacation rentals in Winchester

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Winchester pet-friendly home rentals

Pet-friendly house rentals

Top guest favorite
Home in Lookout Mountain
4.99 out of 5 average rating, 123 reviews

Dog/Family Friendly Mountain Gem near Attractions

ClaytonRating, 5 stars1 week ago
We had such a great stay here. Easily the most responsive and helpful hosts we’ve ever encountered. Highly recommend!
Guest favorite
Home in Trenton
4.96 out of 5 average rating, 159 reviews

Mountain Dale Retreat

ThereseRating, 5 stars4 weeks ago
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!
Guest favorite
Home in Lookout Valley
4.96 out of 5 average rating, 298 reviews

Chattanooga - The Isbill House

Mary ClaireRating, 5 stars3 days ago
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.
Guest favorite
Home in Sewanee
4.91 out of 5 average rating, 184 reviews

Return Guest House and Writers’ Retreat

SandraRating, 5 stars3 weeks ago
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.
Guest favorite
Home in Sewanee
4.92 out of 5 average rating, 118 reviews

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

ChristopherRating, 5 stars4 days ago
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.
Guest favorite
Home in Tracy City
4.95 out of 5 average rating, 20 reviews

Stay ON a Waterfall—13 acres! Bluffs, deck, views!

MarkRating, 5 stars1 month ago
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!!
Top guest favorite
Home in Lookout Valley
4.96 out of 5 average rating, 443 reviews

Star Cottage 2

KatelynRating, 5 stars2 weeks ago
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.
Top guest favorite
Home in Tullahoma
4.98 out of 5 average rating, 59 reviews

Beautiful cottage next to Tims Ford Lake

KellieRating, 5 stars3 weeks ago
Great place to stay, good location and beautiful house.

Pet-friendly home rentals with a pool

Superhost
Home in Winchester
5 out of 5 average rating, 3 reviews

Barefoot Breeze

AustinRating, 5 stars2 days ago
Beautiful place we enjoyed our stay would love to come back if we are back in town.
Guest favorite
Home in Winchester
5 out of 5 average rating, 9 reviews

Twin Creeks Getaway, Pet Friendly!

CharlotteRating, 5 stars1 month ago
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.
Top guest favorite
Cabin in Dunlap
4.98 out of 5 average rating, 104 reviews

Heaven’s View Lodge, Pool, Pet Friendly

LindaRating, 5 stars3 days ago
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!
Guest favorite
Home in Gruetli-Laager
4.95 out of 5 average rating, 20 reviews

Pool, Huge Backyard - Near Hiking & The Caverns

CariRating, 5 stars5 months ago
House was beautiful! Kevin was super accommodating & quick in responding to any questions we had. Would definitely recommend!
Guest favorite
Home in Winchester
4.93 out of 5 average rating, 54 reviews

Basecamp Retreat TimsFordLake

SharonRating, 5 stars1 week ago
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!!
Superhost
Home in Chattanooga
4.71 out of 5 average rating, 7 reviews

Quail Run Farm: Pool Home, 15 Mins to Chattanooga

MollyRating, 5 stars1 month ago
Great stay near Chattanooga! We arrived at night then in the morning loved getting to look around the beautiful property. Would definitely recommend!
Superhost
Home in Sewanee
4.79 out of 5 average rating, 19 reviews

Forest Retreat: Poolside Bliss Close to Campus

SamanthaRating, 5 stars1 month ago
A lovely stay, beautiful, peaceful, perfect
Top guest favorite
Home in Winchester
5 out of 5 average rating, 22 reviews

The Modern Mainstay at Barefoot Bay

PatrickRating, 5 stars1 month ago
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

Superhost
Home in Sewanee
4.86 out of 5 average rating, 22 reviews

Summer Sewanee Lake House

RayvinRating, 5 stars1 month ago
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.
Guest favorite
Cottage in Kelso
4.97 out of 5 average rating, 77 reviews

Bluebird Rest- Peaceful Lake Retreat

ShannonRating, 5 stars4 weeks ago
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!
Guest favorite
Cabin in Sequatchie
4.96 out of 5 average rating, 71 reviews

Fireside Cabin on the Bluff

RobbyRating, 5 stars4 weeks ago
Fiancé an I wanted a private get away, had eveything we needed, amazing view, nice to wake up to the birds chirping.
Top guest favorite
Cottage in Tullahoma
4.98 out of 5 average rating, 64 reviews

Tims Ford Lake Retreat - The Got-Away

IsyanaRating, 5 stars2 weeks ago
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!
Guest favorite
Cottage in Tullahoma
5 out of 5 average rating, 27 reviews

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

JamieRating, 5 stars8 months ago
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!
Top guest favorite
Cottage in Kelso
5 out of 5 average rating, 24 reviews

Clementine Cottage

DarleneRating, 5 stars10 months ago
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.
Guest favorite
Home in Estill Springs
4.94 out of 5 average rating, 36 reviews

“The Country” Lake House w/ Private Dock

KyleeRating, 5 stars6 months ago
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
Top guest favorite
Townhouse in Winchester
5 out of 5 average rating, 17 reviews

AquaHallics Retreat 2

RobRating, 5 stars4 weeks ago
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