Pet-friendly vacation rentals in Winchester

Very pleasurable stay, nice private location and excellent communication. 5 stars!

Our group of 10 loved Kathryn’s home. We were in town for our 25th Sewanee reunion and it was perfect. The home has wonderful areas to visit and relax. It was very clean and had everything we needed. Kathryn offered to stock our fridge and provide restaurant recommendations. I would highly recommend this home to anyone visiting Sewanee.

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.

If you’re going to golf at Sweetens, you couldn’t get much closer. Huge place for a big group. Well done.

Return House was exactly what we needed for a perfect weekend in Sewanee. The location is very close to the University of this South, and yet feels like it is secluded in the forest. Michael’s home is warm and comfortable, and I especially enjoyed listening to the birds while enjoying my morning coffee on the deck. Check in was easy and Michael is a great host. We will definitely stay here again!

Fran was proactive and extremely easy to deal with, making this a perfect getaway for my wife and I. Great value for the price and location made it an easy walk to the downtown and distillery.

We visit the area often and Matt's place was by far our favorite. It truly feels like a home and has everything you need to make for a comfortable visit. We look forward to staying here again soon!

Amanda was super kind, responsive, and friendly. The place was full of character. Exactly the kind of place we wanted.

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.

These young ladies have created an amazing jewel of a place for others to enjoy. This container home exceeded any expectation that we had. Our large family had plenty of space and enjoyed having their own private suite. Each year at Christmas we go to different location for our annual Christmas family vacation. This home will be the one place that we all agree that we will be back! Everything from the lush towels, to the fully equip kitchen which allowed us to keep the tradition of each couple taking a night to cook for the group. The sauna was so fun, the patio was a great family space. I can’t say enough about this place. Thank you for allowing us to enjoy your home. May God continue to bless you.

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.

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.

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!

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

Our family, which included 6 adults and 4 children, all had a great time. We enjoyed the outside area including the firepit and nearby hikes.

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

Pictures don’t do it justice, you walk in, it is beautiful, peaceful, in my opinion, perfectly decorated and extremely comfortable. Could not have been better! Sheila was a very responsive and lovely host.

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!

Perfect place for our family Christmas!! we had such a great time and the house was perfect for our group. The host went above and beyond expectations with little touches that were so awesome. the upstairs was perfect for family game night. Plenty of space to spread out. Winchester is a beautiful town with plenty to do in town. Don't miss out on visiting the Merchantile. We will certainly be looking to rent this place again!!

Perfect place to disconnect, relax and enjoy nature. we love it

We love this area and this development of tiny homes is a great option for our family. Linda’s place as exactly as advertised and very clean and comfortable.

We had the best stay with our kids here on the farm. We played quite a lot with the animals. Very comfortable and peaceful. Laurie and Donald are very friendly and personable. We enjoyed talking to them and seeing them during our stay. You won’t find anything else like this. We will be back again.