Pet-friendly holiday rentals in Winchester

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Popular amenities for Winchester pet-friendly home rentals

Pet-friendly house rentals

Guest favourite
Home in Flintstone
4.94 out of 5 average rating, 410 reviews

★ Mountain View Cottage ★

Mandy (Amanda)Rating, 5 stars2 days ago
Location! location! Jeff’s place felt just like our cottage on the lake in Ontario. Quaint, clean, fully stocked and came with sweet extras like a bottle of wine for us and a dog bone for our fur baby. You cannot beat the location ! We wish we had more time to spend in the area! A great bonus is the yard space for our dog and we sat like a couple of old fogies and had our wine on the front porch during a thunderstorm. Jeff was extremely responsive and accommodating. Thank you for sharing this gem with us!
Guest favourite
Home in Walker County
4.91 out of 5 average rating, 56 reviews

~Peach Hill House~ Family & Pet Friendly!

GeoffRating, 5 stars1 week ago
Standouts - included kitchen appliances, dishes and flatware were over the top - we needed nothing to prepare dinner for 7! Separate bedrooms with comfy beds and a sleeper couch for our grandson. Recreational add-ons of pool table & dartboard in the game room with the projector wall screen tv with surround sound was a big hit. The backyard had a HUGE deck with a patio covered shelter area with room for 8 people to sit around a table and talk. I had morning coffee out there every morning by myself and listened to the birds. I used my Merlin ID app that listens and identified birds. It listed 15 different birds inside of 4-minutes. EVERYTHING is close - Rock City, Lookout Mountain are literally viewable from the nearby thoroughfare. The aquarium took us about 15-minutes to reach. Food stores very close - coffee shops etc. The hosts had everything covered - including coffee pods, ground coffee, extra paper towels, a blender, toaster, etc etc etc. We wanted for NOTHING. We’ll be coming bac
Guest favourite
Home in Estill Springs
4.92 out of 5 average rating, 12 reviews

Spacious 4 bedroom 2 bath house

EmilyRating, 5 stars2 weeks ago
This quaint little house is Estill Springs is perfect for a family or a few couples to get together and not be too in town but also close enough to anything you might need. Plenty of space and things to do from movies to games and the screened in porch out back is very nice to relax and listen to the sounds of nature! It’s close to family and we will likely be back in the future!
Guest favourite
Home in Chattanooga
4.97 out of 5 average rating, 445 reviews

Boutique St Elmo Farmhouse 7 min from Downtown

JerelRating, 5 stars1 week ago
We had a fantastic weekend at Nathaniel’s place! The house was spotless, cozy, and exactly as shown in the photos. The neighborhood is beautiful and peaceful-perfect for a relaxing getaway. Our three Frenchies loved it too! There was plenty of space for them to play, and the quiet surroundings made it easy for all of us to unwind. Nathaniel was a thoughtful host, and everything we needed was provided. We highly recommend this home to anyone looking for a comfortable stay in a lovely area. Thank you for a wonderful experience!
Guest favourite
Home in Lookout Valley
4.96 out of 5 average rating, 280 reviews

Chattanooga - The Isbill House

JonathanRating, 5 stars1 week ago
Beautiful home. Centrally located to everything downtown and lookout area. Inside is peaceful and no interstate noise. Outside, can be at times, but it’s hardly noticeable
Guest favourite
Home in Sewanee
4.91 out of 5 average rating, 182 reviews

Return Guest House and Writers’ Retreat

HillRating, 5 stars1 week ago
Lovely place in the woods with immaculate Inside. Check in was super easy. Had everything we needed. Will stay here again and again.
Top Guest favourite
Home in Lynchburg
4.99 out of 5 average rating, 72 reviews

Sunshine’s- Pet friendly, walk to town square & JD

AmandaRating, 5 stars1 day ago
We stayed in Lynchburg for about a month. This place was perfect! We arrived later in the evening and were happy to have an easy check in. The house looks exactly the same as the photos. It's in a quiet, safe, and well maintained neighborhood. Very close yo downtown Lynchburg & Jack Daniel's. We specifically booked for the ease of traveling to Alabama, Chattanooga, & Nashville. There's lots of great state parks close by, hiking trails, & waterfalls. Fran was an excellent host. She was very responsive to all our questions. We would definitely stay here again!
Guest favourite
Home in Beersheba Springs
4.9 out of 5 average rating, 123 reviews

Modern Space in the Heart of Beersheba Springs

StephanieRating, 5 stars6 months ago
Amanda was super kind, responsive, and friendly. The place was full of character. Exactly the kind of place we wanted.

Pet-friendly home rentals with a pool

Superhost
Home in Winchester
New place to stay

Barefoot Breeze

LaterriaRating, 5 stars3 weeks ago
I loved that the neighborhood was peaceful, beautiful & surrounded by a stunning lake. Every morning we would open the crank windows in the primary bedroom to get an unobstructed view of the lake & trees. The neighborhood was private during the weekdays. A diverse group of families move into the neighborhood towards the weekend. It's actually quite lovely to see the small children from the different homes playing together while the adults gather on front porches & around patio fireplaces. I liked that the home has lots of windows that let in sunlight. The bathrooms were pristine & the beds were comfortable. I adored the are barn doors in the home that complement the natural surroundings of the lakeside community. There was a cabinet full of boardgames. They provided plenty cookware, dishes & toiletries. The 4 kayaks that come with the rental were just enough for my spouse, 2 sons & myself. They also provided life vests. Twin Creeks marina is 5 minutes away & Walmart is 8 minutes away
Guest favourite
Guesthouse in Lookout Valley
4.81 out of 5 average rating, 21 reviews

Chattanooga pool vacation home!

MeghanRating, 5 stars4 weeks ago
Very nice and peaceful! Loved the hanging swings. Loved that it had some kids toys!
Top Guest favourite
Home in Trenton
5 out of 5 average rating, 15 reviews

Spa, Fire Pit, 2 Kitchens, 5 Baths, 15m to Chatt!

KristaRating, 5 stars2 weeks ago
Mike and Brianna are super-hosts in every way. Very accommodating, flexible, communicative, always available and just great to interact with. Home is everything you see in the photos and more. Lots of amenities. Barely left the house because the house has so many amenities for all 6 guests with differing ages and personalities. You can't go wrong renting this home with Mike and Brianna. You won't regret it - That's for sure.
Top Guest favourite
Cabin in Sewanee
5 out of 5 average rating, 36 reviews

Bougie Moms Cabin! Hot Tub|Sauna|Theatre

ErinRating, 5 stars1 month ago
Absolutely amazing!! It was beautiful and fully stocked to be peaceful. They were prompt with responses and very friendly. 100% recommended. I'll be going back for sure!
Guest favourite
Home in Winchester
4.92 out of 5 average rating, 50 reviews

Basecamp Retreat TimsFordLake

AndreaRating, 5 stars2 weeks ago
Thank you Emily for letting us book your Airbnb. Your property was amazing & perfect for a relaxing Easter weekend with my husband & adult sons. Very clean and inviting. The kitchen was excellent to cook in and well supplied. We gathered at the island for meals & sat on the patio with the gas/wood fire fireplace at night. In a gated community & only a few miles from the marina! It was just perfect! Thanks again!
Guest favourite
Home in Gruetli-Laager
4.95 out of 5 average rating, 20 reviews

Pool, Huge Backyard - Near Hiking & The Caverns

CariRating, 5 stars4 months ago
House was beautiful! Kevin was super accommodating & quick in responding to any questions we had. Would definitely recommend!
Guest favourite
Home in Sewanee
4.93 out of 5 average rating, 14 reviews

Forest Retreat: Poolside Bliss Close to Campus

DavidRating, 5 stars3 weeks ago
Absolutely awesome location and home. kitchen is absolutely awesome and has all you need. There are 3 bedrooms and a loft bedroom that is right outside another bedroom. So plenty of private spaces for guests to be at alone or in the commons spaces. Outside there is the front patio with rockers, a fire pit and chairs around that, a table and chairs and then the loungers around the pool. So much space to spread out in. One of the neighbors is out daughter's advisor at Sewanee, so that was really neat. Easy access to both Winchester and Mont Eagle. No issues at all, and hosts replied very quickly with questions we did have and checked on us also. Definitely will return!
Top Guest favourite
Home in Winchester
4.95 out of 5 average rating, 22 reviews

The Modern Mainstay at Barefoot Bay

PatrickRating, 5 stars2 weeks 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

Top Guest favourite
Home in Lookout Mountain
4.95 out of 5 average rating, 60 reviews

7 Bdrm 25ppl~ Real Beds ROCK CITY AREA- Firepit

AhmadRating, 5 stars1 month ago
We appreciate your quick responses and helpful recommendations.” “Staying with Marcie was a pleasure. The location was perfect, the home was cozy and clean, and Marcie was always available to answer our questions. Highly recommended!”AAAA+++
Guest favourite
Home in South Pittsburg
4.97 out of 5 average rating, 37 reviews

14 Bed Log Cabin on Sweetens Cove

RyanRating, 5 stars1 month ago
This place was as described. I would stay here again. Especially if you're playing golf at sweetens. Perfect place for you and your friends to stay and play.
Guest favourite
Farm stay in McMinnville
4.91 out of 5 average rating, 123 reviews

Studio House

KristinRating, 5 stars2 weeks ago
Stacy's listing was comfortable, quiet, and safe. I loved interacting and watching the various animals on the property. I learned how each animal contribute to the space, which was interesting & hopefully one day I can contribute to my property in a similiar manner. The stars are brighter in places like this and the lack of traffic noise is always a major plus. Children would enjoy the various furry friends here too.
Guest favourite
Apartment in Sewanee
4.96 out of 5 average rating, 51 reviews

Loft at Sewanee

SissyRating, 5 stars4 weeks ago
This is the second time I’ve stayed in this lovely apartment. Both times I felt right at home. The space has everything you need to be comfortable during your time on the mountain. The hosts are so friendly and accommodating as well. I would definitely recommend this place to anyone looking for a comfortable, convenient spot to stay on campus. It is so nice to have Amenities like a full kitchen and washer and dryer too!
Top Guest favourite
Home in Tullahoma
4.98 out of 5 average rating, 54 reviews

Beautiful cottage next to Tims Ford Lake

JenniferRating, 5 stars1 month ago
We stayed here for 2 nights. Matt was very accommodating and we were able to check in a little early. The home was very clean. The kitchen was stocked well with items you would need to cook as well as other items throughout the home such as shampoo and conditioner. Town was about 15 mins away, with a dollar general about 6 mins away. There were many beautiful waterfalls in the area to check out (Rutledge Falls and Old Stone Fort). Overall our experience was a 10/10. I would definitely visit again. Thank you Matt!
Top Guest favourite
Cabin in Estill Springs
4.96 out of 5 average rating, 266 reviews

Holliday Hide Away

DustinRating, 5 stars1 day ago
We have had multiple stays with Ray and Deb and it’s always been a wonderful experience. They are great hosts. The cabin is always clean and perfect for a short getaway
Top Guest favourite
Cabin in Whitwell
4.98 out of 5 average rating, 57 reviews

The Kolts at Camp Chet (930 forested acres!)

ReneeRating, 5 stars1 month ago
My family and I chose to get out and spend some time outside during spring break this year. I couldn’t have asked for a better place! Robert was very easy going and very responsive, even a few times when we lost our way around.. he picked right up and was very helpful! I would recommend this stay to anyone! Great people and great place to spend family time!
Superhost
Home in Lookout Mountain
4.73 out of 5 average rating, 92 reviews

Peaceful Mountain Hideaway near Attractions

JessicaRating, 5 starstoday
Corey’s place was cute and clean and quick to respond. It had everything you needed for a nice getaway. It was clean and very cozy. Everything we wanted to do was about 15 mins away. Which was super nice. There is a dollar general right down the road which was very convenient. All in all we had an amazing trip.

Quick stats about holiday rentals that are pet-friendly in Winchester

  • Total rentals

    30 properties

  • Nightly prices starting at

    $93 AUD 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