Pet-friendly holiday rentals in Winchester

Our family of four, including two young kids, had a wonderful stay! We mainly used the space for sleeping and breakfast, and it was perfect for our needs. The beds were incredibly comfortable, and we especially enjoyed the spacious bathtub. Our kids absolutely loved watching the chickens roam around, which added such a fun touch to our stay. The trail in the back was a great bonus, and waking up to the sound of the rooster in the mornings made the experience even more charming. Loved the quite away from the city. Just what we needed.

Kathryn is the BEST host! Have been staying here for 3 years and each time we come we love it even more. The house is always immaculately clean and prepared when we arrive. Kathryn was super responsive to anything we needed during our stay! Already rebooking!

Love this Place. Beautifully remolded historic home that is Extremely well taken care of. I stay here every year I come to Feb Jam, it's always my first choice.

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.

My kids and I went for the weekend and honestly wished we had a couple days longer to stay. The house was welcoming and the host made sure to leave lights on and doors open for us to get in with ease. Randy was extremely easy to work with. The lake was nice and the boat rental process was quite convenient…there was even a tube for a fantastic tubing experience! I’d recommend staying here!

Such a great stay. We loved the stools on both sides of the bar and the way the kitchen was open to the family room. The kitchen was fully stocked with dishes and cooking supplies. They could have used more dis towels, but we made do with paper towels. Comfortable beds and the down comforters were wonderful. The communication was amazing. They were super quick to respond when I sent a message. I highly recommend staying here. It is great for larger groups. We had 7 people and it was perfect.

This home exceeded our expectations—it was even better than the pictures! The decor is charming, and the space feels warm and inviting. The master bed was incredibly comfortable, and my wife and I slept so well every night. The kitchen was fully stocked with everything we needed, making meal prep a breeze. Matt was very responsive and went above and beyond to accommodate our specific needs, ensuring we had an stress-free stay. The neighborhood was peaceful and private, providing a serene retreat. Additionally, its proximity to Tims Ford State Park made it convenient for us to explore the park’s beautiful trails and lake activities. Highly recommend Matt’s place for those looking for a peaceful getaway and excellent host!!!

Highly recommend. Chris was very responsive and easy to communicate with. The home was beautiful and the view was amazing! We had a relaxing long weekend fishing off of the dock and making memories with our friends and family. We would stay here again.

We loved our stay at BaseCamp! Communication with Emily was excellent. The house was amazing & conveniently located. It is beautifully decorated & comfortable. We loved the screened in porch & having access to a wood burning fireplace. The views of the lake & surrounding trees were beautiful & peaceful. The community pool area is within walking distance & offers other beautiful views. Downtown Winchester is so charming! We loved Filo’s Tavern (great service & cocktails, delicious food & get the carrot cake!), Walnut Hill Coffee Co. (cool vibe, great coffee & try their breakfast tacos), and Piezan (great service & generous portions). We loved Basecamp so much we tried to extend our stay but they were already booked up. Such a positive Airbnb experience. We look forward to a future visit!

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.

Mark’s house was absolutely gorgeous! It is situated on a beautiful piece of property right on the lake with the most spectacular deck. We spent most of our time either on the deck enjoying the peace and quiet of the lake or in the cozy entertainment room. The house was ideal for our stay. We had 5 couples. Three of the bedrooms are spaced out with en-suite bathrooms. Two of the bedrooms create a family suite that share a bath. We appreciated the cleanliness of the home and overall quality of the space. The house was fully stocked with just about anything you could possibly need. This home is a very special place and we will look to book again the next time we visit the area. Thank you, Mark!

This is a great house with a huge yard. It was winter, so the pool wasn't used, but the firepit is nice. It's a great location, a bit out of the campus hustle, yet very close to everything "University". Although it did not bother us at all, it's a bit of a noisy spot during the commute hours, as the road beside it brings a good bit of traffic in for work. We highly recommend this listing!

We had a very comfortable stay, and Korina was quick to respond to any questions. We hope to come back!

Great stay! We really appreciated the noon check-out. We’d definitely stay again if we are ever in the area again.

We very much enjoyed staying at Kari’s house. The kitchen had all of the things we needed to cook group meals. The neighborhood was beautiful and fun to walk around. The grill and patio was a great setting for the warm evening dinner. Dog friendly!

Easy access to house, beautiful home and a very quiet neighborhood. Loved the back screened in porch to sit and look at lake. Very roomy and open floor plan made it easy to visit with family. Very spacious kitchen and refrigerator. Bedrooms were very roomy and the bunk beds were a great touch for the kids. The upstairs was super for a quiet work environment or just a quiet relaxing getaway within the house. Truly felt right at home while I was there. If it matters to anyone the washer and dryer were front loaders and convenient to the kitchen. A great asset to the rental is the golf cart to enjoy a ride through the neighborhood in the evening as the sun goes down. Hunter was a great host and always very responsive to my email. Check in and out was super easy and there was very little asked of host for us to do in order to check out. I really enjoyed my stay, location, and the home. I will stay with Hunter again and 100% recommend him as a host and his property.

Great place to get away and enjoy yourself for the weekend place was nice and clean easy to find very private with great amenities Will stay again in the future place is absolutely beautiful

What a beautiful property. A peaceful and comfortable stay at a high end Airbb. Wish they could all be at this comfort level. Host was very accommodating. Location was good for visiting sites. Highly recommended!

Just had a wonderful stay at Endless View Cottage! I was there to visit my daughter at Sewanee and could not have asked for anything more. It is an easy drive to campus, restaurants and the grocery store. The cottage is so cozy and comfortable and had everything I needed. It is a great place to relax, catch up and enjoy and the view is amazing! I would stay here again in a heart-beat!

It was absolutely stunning! we enjoyed our stay and Jacqueline helped us with anything we asked and gave great recommendations 😀 we can't wait to go back!

We stayed at Heather's Airbnb for a cozy, reading weekend and it was the perfect pick! The kitchen and bathrooms were stocked with everything we needed and more. We really enjoyed waking up to such a bright, beautiful space with tons of natural light. It was such a peaceful area, and we loved getting to take a reading break to go for a walk near the lake or sit on the dock. Having a private hot tub and a screened in patio with a fireplace was also a huge plus! Heather was responsive and proactive in making sure we had everything we needed, and was quick to answer any questions we had. We felt very taken care of during our time in Tracy City. We really enjoyed our weekend at Heather's and will certainly be back!

Super clean, comfortable, and close to town. Beautiful walking trails right outside the home. Bethany was easy to communicate with and responsive. I would definitely stay here again!

Wonderful host and location. Booked last minute and host was extremely responsive and quickly made sure booking was ready for our arrival. This is a fantastic home, everything is high quality and very well thought out. It’s in a quiet private community with easy access to plenty of great local attractions and restaurants. We did not take advantage of the included boat slip this time, but definitely will when we stay here again.

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!