
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

Snuggle Up in our Teddy Cottage!
A perfect place to stay between The Caverns and Denny Cove!

Mountain Dale Retreat
Beautiful house and friendly host. Not far from Chattanooga and all necessities are close by. Will stay here again if I'm back in the area.

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

Boutique St Elmo Farmhouse 7 min from Downtown
Absolutely wonderful home pristine condition. Perfect area, safe restaurants, entertainment everything was in a very close by within 10 minutes coming back October or November will definitely book the same particular place again it was absolutely wonderful. Host was fabulous. Any issues I had like trying to figure out the Wi-Fi or something really simple it was very quickly helped with recommend this place strongly. Quick response extremely clean home once again definitely would rebook this Airbnb. I travel a lot and this was one of the better homes I had. Thank you again

Return Guest House and Writersâ 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
I thought the listing was excellent value especially as a dog owner. We had 4 adults and 2 large dogs and it was comfortable and convenient for everyone involved. I didn't have any issues to speak of, it was clean and the owners were responsive and very pleasant to interact with.

Star Cottage 2
My husband, our 2 dogs, and I stayed here for a weekend. Nice fenced in yard in a quiet neighborhood, yet still close to downtown and all the happenings of Chattanooga!

Beautiful cottage next to Tims Ford Lake
Matt was very sweet and gave us many helpful tips during our stay! I would 100% recommend this place to anyone who is trying to have a peaceful and laidback vacation!
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.

Heavenâs View Lodge, Pool, Pet Friendly
Heavenâs 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 Heavenâs View!

Bougie Moms Cabin! Hot Tub|Sauna|Theatre
We loved our time at the Bougie Momâs Cabin! Rachel and Steph really thought of everything! The beds were super comfy. The coffee bars with snacks were such a nice touch. We also loved the set up. Our families separate container homes for when they wanted privacy/quiet time. The swinging chairs on the patio of the tree house and the views were amazing! The swings were the grand-babyâs favorite! And so peaceful. We hated we could not stay longer. Next time we will stay longer.

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 donât 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!!

308~Brand New~PET FRIENDLY~Super Clean DOWNTOWN
Ashleyâs place was perfect for a quick getaway for myself and my toddler. We were able to get to the Childrenâs museum via quick drive & walk to several restaurants for meals. The building was quiet & she was very responsive.

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

The Modern Mainstay at Barefoot Bay
Korina was very kind and responsive we absolutely loved to stay their and would definitely stay again!

Gorgeous lake home in Twin Creeks with Lake View
Beautiful lake view. Nice outdoor living space with TV for sports enthusiasts which I was traveling with. Take golf cart to the marina for happy hour and standard bar fare. Nice neighborhood!
Private, pet-friendly home rentals

Little Green Cottage
Perfect place to stay for a concert at the caverns! Peaceful and beautiful!

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.

Stay ON a Waterfallâ13 acres! Bluffs, deck, views!
The best stay ever! Can't beat this location. The hiking was great! The sound of the falls were so peaceful. Beds were comfortable. I've stayed at 40+ airbnbs and this one is at the top. Great host, too! Can't wait to come back!

Swordfish Suite - Pup Shed Retreat
Awesome place with tons of great outdoor activities. Nice community with good public spaces. Comfy beds, great ac, easy access to amenities. Pup shed was a great additional space. Host very prompt to communicate as well. Would definitely stay again!

Little Bird Cottage
It was the perfect place and we loved it! Very well kept and had everything we needed. Beautiful setting with lake out the back door! It was on campus and a short distance from all that we needed! I highly recommend Lindsey and her cottage!

AquaHallics Retreat 2
This place was great! It was beautiful and clean. Had everything you needed for your stay. We had a last minute booking and a bad situation with another place and they were able to get us right in. We really appreciate the hospitality and hope to be back again.

Lakefront Tiny Home/Pet Friendly
This place made me want to buy a tiny home! Absolutely beautiful and being right on the lake made it just about perfect. Great location for a concert at The Caverns and wonderful hiking. Iâve always loved Tennessee but this area was too cute!

The Cozy Cottage at Tim's Ford Lake (Sleeps 6)
I appreciated the smooth check-in to the last day I was there, Kim was always responsive and quick to resolve any issue I had. The place was clean and very comfortable with a fully functional kitchen was much valued. I would recommend staying at this great place and the friendly help with Kim. Thank you Fred K.
Quick stats about vacation rentals that are pet-friendly in Winchester
Total rentals
30 properties
Nightly prices starting at
ïș©.ïș220 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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- Rentals with outdoor seating Winchester
- Kid-friendly rentals Winchester
- House rentals Winchester
- Rentals with a fireplace Winchester
- Rentals with a kayak Winchester
- Cabin rentals Winchester
- Rentals with pools Winchester
- Rentals with a fire pit Winchester
- Rentals with lake access Winchester
- Family-friendly rentals Winchester
- Rentals with a patio Winchester
- Rentals with a washer and dryer Winchester
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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
- The Ledges
- Chattanooga Choo Choo
- Coolidge Park
- Creative Discovery Museum
- The Lookout Mountain Club
- Old Fort Golf Course
- Hunter Museum of American Art
- National Medal of Honor Heritage Center