Pet-friendly vacation rentals in Winchester

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Popular amenities for Winchester pet-friendly home rentals

Pet-friendly house rentals

Guest favorite

Home in Northside

4.99 out of 5 average rating, 145 reviews

3min to Aquarium | Secret Game Room | 3 King Beds

ThomasRating, 5 stars6 days ago
This place was great and it was as advertised. You can tell they care a lot about the details and made sure to make your stay one to remember. The house resembled the pictures to a T. The owners were responsive and made sure to check up on us during the stay. I’ll be staying here again when we come through Chattanooga!
Guest favorite

Home in Trenton

4.95 out of 5 average rating, 148 reviews

Mountain Dale Retreat

RhondaRating, 5 stars1 week ago
We chose Shannon’s place for our annual cousin weekend. It was perfect for our needs and we enjoyed it immensely! Very spacious house, well stocked kitchen, big comfy beds, pretty view, so much attention to detail evident throughout the home and Shannon was very responsive. Would highly recommend!!
Guest favorite

Home in Flintstone

4.94 out of 5 average rating, 396 reviews

★ Mountain View Cottage ★

SandyRating, 5 stars1 week ago
We really enjoyed staying here. Was very cozy and very quiet. Bed was super comfy. Really nice. Highly recommend.
Guest favorite

Home in Chattanooga

4.97 out of 5 average rating, 428 reviews

Boutique St Elmo Farmhouse 7 min from Downtown

LeAnnRating, 5 stars1 week ago
Nate and Dene were responsive hosts and were flexible and allowed us to check-in a few hours early. The house has been redone tastefully. Beds were very comfortable, kitchen was well-equipped with plenty of plates and glasses, towels and bed linens were of higher quality. Check-out instructions weren't long and complicated. This house is located within easy distance to many of the standout Chattanooga attractions and to grocery stores and several restaurants.
Guest favorite

Home in Lookout Valley

4.97 out of 5 average rating, 253 reviews

Chattanooga - The Isbill House

AmberRating, 5 stars1 week ago
I came down to stay for a few days after surgery. Amanda’s place was the perfect spot for us and we do hope to be back in the area to stay again soon!
Guest favorite

Home in Sewanee

4.91 out of 5 average rating, 177 reviews

Return Guest House and Writers’ Retreat

CharleneRating, 5 stars2 months ago
Michael was a kind host. The cabin was gorgeous and larger than what the pictures demonstrate. Close to fun hiking areas.
Guest favorite

Home in North Chattanooga

5 out of 5 average rating, 122 reviews

Northshore Urban Hive - Spacious House with EV Cha

CallieRating, 5 stars1 month ago
Our family had a wonderful few days here! We loved the location and walked to the North Chattanooga shops and along the river as well as across the river to Bluff View and downtown. Having grown up on nearby Signal Mountain, it was a great way to have our family together here in Chattanooga again! Hosts were personable and professional.
Superhost

Home in North Chattanooga

4.78 out of 5 average rating, 100 reviews

North Chattanooga! 5 min from downtown

StephanieRating, 5 stars2 months ago
Stayed here over thanksgiving as a remote work spot while we climbed on days off. Was exactly what we needed for this trip!

Pet-friendly home rentals with a pool

Guest favorite

Guesthouse in Lookout Valley

4.8 out of 5 average rating, 15 reviews

Chattanooga pool vacation home!

MichaelRating, 5 stars2 months ago
Perfectly chill home very close to Chattanooga. Simple, clean, relaxing walk-in basement apartment with a fantastic porch area next to the pool. Unfortunately the pool was winterized and not available (it was November) but even without the pool Paige’s house was great. Our second night we had a fire in the little solo stove on the pool deck, (plenty of firewood at the ready). Plenty quiet, we weren’t even sure if anyone was home upstairs. Only one bedroom but with the day bed and sleeper sofa there was room for us and our kids. Great stay, definitely on our list for our next Chattanooga visit.
Guest favorite

Cabin in Dunlap

4.99 out of 5 average rating, 91 reviews

Heaven’s View Lodge, Pool, Pet Friendly

JocelynRating, 5 stars3 weeks ago
Great place to stay! We went with our toddler as a get away before we have baby #2. We stayed 5 days and didn't feel the need to leave the entire time. Plenty of things to do for all of us, cozy, kitchen is well stocked with almost everything you could need to make meals, fire place was cozy, Christmas decor was beautiful, master bath tub was super relaxing, and the beds were comfy! I would 10/10 recommend. Looking forward to hopefully back when it's warm so we can use the pool!
Guest favorite

Home in Trenton

5 out of 5 average rating, 9 reviews

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

MelissaRating, 5 stars1 month ago
Breathtakingly beautiful home with well mantained, spacious yard. I appreciate that the photos were spot on and actually didn’t do this home justice. The classy furnishings and furniture made this the best Airbnb I’ve been to so far. Thank you for accommodating my family for the holidays with a Christmas tree, candy tray and wine. I 100% refer this home.
Guest favorite

Home in Gruetli-Laager

4.95 out of 5 average rating, 19 reviews

Pool, Huge Backyard - Near Hiking & The Caverns

DougRating, 5 stars1 month ago
This was a wonderful place to gather with family for Christmas. Kitchen was well stocked and you can tell the owners treat it as their own.
Superhost

Home in Trenton

4.83 out of 5 average rating, 102 reviews

Sunset Haven: Pool with Stunning Views!

LorenaRating, 5 stars3 weeks ago
This property was lovely. Great location for going to lookout mountain. The road leading to the house definitely needs to be paved but it was clearly mentioned in the descriptions so it wasnt a surprise. Amber was very quick to respond to the few questions we had. She was great. The view was stunning. The weather was windy and cold so we sadly couldnt explore the property but we would love to come back in the future. Definitely recommend this listing.
Superhost

Condo in Chattanooga

4.78 out of 5 average rating, 341 reviews

308~Brand New~PET FRIENDLY~Super Clean DOWNTOWN

EmmaRating, 5 stars3 weeks ago
A great place to stay while visiting Chattanooga! As a native, it was awesome to feel like a tourist in my hometown and get to be in the middle of everything. We were so grateful that Ashley accommodated our cats. Overall, an amazing experience!
Guest favorite

Home in Winchester

5 out of 5 average rating, 19 reviews

The Modern Mainstay at Barefoot Bay

GretelRating, 5 stars2 months ago
Beautiful house and great host - we had a fantastic time at this house! The house is across the street from the lake and very close to the town square - super cute shops and restaurants and even an old-timey movie theater. They offered free Christmas movies as a black-Friday event. We really enjoyed our Thanksgiving stay.
Guest favorite

Home in Sewanee

4.9 out of 5 average rating, 10 reviews

Forest Retreat: Poolside Bliss Close to Campus

ElizabethRating, 5 stars1 month ago
This house has a great location in Sewanee. It is stocked with everything we needed for our 3 night stay. Very comfortable home, nicely decorated and plenty of space. Hope to come back again.

Private, pet-friendly home rentals

Guest favorite

Tiny home in Tracy City

5 out of 5 average rating, 29 reviews

A-Frame Nature Getaway/Lake Access/Pet Friendly

McKenzieRating, 5 stars4 weeks ago
Hiker’s Hideaway was absolutely incredible. It was cozy with a dozen small touches that made it feel like home during the holidays. You could sense that intention was put into every detail of the stay. Fiery Gizzard was only a short drive away and all of the games provided at the house made staying in for New Year’s Eve so much fun. We can’t wait to come back!
Guest favorite

Cottage in Winchester

5 out of 5 average rating, 7 reviews

Waterfront Cottage #7 - "Dog Daze" PET friendly!

MarthaRating, 5 stars1 month ago
My family (5 including 3 teen boys) spent Christmas week here and had an incredible time. The resort is definitely geared towards Summertime activities but it served the purpose this winter. We went on several incredible hikes and came back to an extremely relaxing Airbnb. The boys loved their private rooms downstairs while we enjoyed the top floor. Cooking in the fully stocked kitchen was wonderful. This was a great week of making memories and I know it'll be the same for the next family to come!
Guest favorite

Farm stay in McMinnville

4.9 out of 5 average rating, 115 reviews

Studio House

KaylaRating, 5 stars1 month ago
This was a life changing experience. I booked last minute after a really hard week, desperately needing an escape from life to just.. exist. My mother was having a very hard time too, so she came with me. We had an absolutely incredible experience. It was so peaceful. We got to pet the goats, see the pigs and chickens and geese, adore the bunnies. Everything was so perfect. I will absolutely be back. It was well worth the price. And Stacy was so responsive and kind. She has a beautiful plot of land, and is a very incredible person. I got to hold a baby goat while there, and I cannot describe the level of healing that did for my soul. Reminding me how fleeting life is. To live in the present moment. Thank you Stacy. You provided the most incredible environment. I cannot thank you enough.
Guest favorite

Cottage in Walker County

4.94 out of 5 average rating, 638 reviews

Big Living in the Little House

CallieRating, 5 stars3 weeks ago
The detached small home was a wonderful place to come back to after long days! The space was very cozy and kept its heat well in the cold. Rodger was so helpful especially when our car’s battery died from the cold. He used his portable jump starter get our car to start and recommended a local car battery repairmen for us to get a replacement. The area was tranquil and the mountains on both sides of the valley were beautiful!
Guest favorite

Guesthouse in Spencer

4.9 out of 5 average rating, 273 reviews

Hannsz Hideaway

MarciaRating, 5 stars3 weeks ago
This was my first experience with Airbnb and I can’t be happier! Great place and wonderful host! I was just staying overnight and heading out early in the am. I hope I make it back here to see all the beauty to this charming place! I have a 5#puppy and so glad she was welcome. I travel back and forth from Florida to Illinois often and this was a great halfway stop for me. I had a couple bad experiences with hotels not being clean or safe, this place feels like home! Thank you!!
Guest favorite

Cabin in Trenton

4.94 out of 5 average rating, 207 reviews

Secluded Country Cabin between city and country

KaylaRating, 5 stars2 weeks ago
My family and I had such a wonderful time at Drew’s secluded cabin. We came right before the snow storm of the year which was exciting but also intimidating since we are from Florida. Drew was so helpful and came to shovel and salt the steps for us. Throughout our stay he was very responsive and helpful with any questions we had. Thank you Drew and Caroline for everything we will definitely be back!
Guest favorite

Guesthouse in Chattanooga

4.97 out of 5 average rating, 261 reviews

The Midvale Guest House

LaurieRating, 5 stars1 month ago
If you’re looking for a place with a fenced back yard, this is perfect! We have small dogs, and at other AirBnB’s I’ve had to find and plug holes under the fence where the dogs could escape. Not here - the fence goes fully to the ground all the way around the perimeter, and we felt totally comfortable letting our girls out to enjoy the sunshine!
Guest favorite

Tiny home in Chattanooga

4.97 out of 5 average rating, 62 reviews

Escape Tiny Two

LizzyRating, 5 stars1 month ago
This place was beautiful it was relaxing and homing. My stay felt like a dream I wish I could live through longer. Everything was as described and even felt bigger and more beautiful in person. Best cozy mountain hideaway ❤️

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    $60 before taxes and fees

  • Total number of reviews

    1.1K 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