House holiday rentals in Winchester

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Winchester

House rentals with a pool

Top guest favourite
Home in Winchester
5 out of 5 average rating, 33 reviews

Lakefront Haven on Tims Ford w/ Kayak and SUP

KyleRating, 5 stars1 day ago
Emily and Randy's lake house is upscale, peaceful and in a great location. Access to the lake and pool are literally right outside your door and the town square, which has several nice restaurants, is a mile down the road. We enjoyed our stay and would definitely stay there again.
Top guest favourite
Home in Winchester
5 out of 5 average rating, 13 reviews

Lakeview Luxe | Lake Access + Pool

Jeff - PFS AmericasRating, 5 stars4 weeks ago
The home was gorgeous and is better than the pictures and description. We had an issue that was our fault. Julianne worked with me and was professional and flexible. I couldn't ask for a better host. I would recommend this home to anyone.
Top guest favourite
Home in Winchester
5 out of 5 average rating, 12 reviews

Gorgeous Lakefront! Pool, Games, Fire Pit, Marina!

KaleighRating, 5 stars2 months ago
Leigh was amazing! The home was beautiful and she was so communicative and sweet. We will absolutely be back!
Top guest favourite
Home in Winchester
5 out of 5 average rating, 12 reviews

Barefoot Dreams

JohnRating, 5 stars3 weeks ago
I’ve probably stayed at over 100 Airbnb’s over the years and this one is definitely in the top three overall. Fully stocked, spotless, convenient, responsive host, and just a wonderful property. Right across the street from the community pool and the lake. Literally couldn’t ask for a better place for a relaxing weekend with families.
Guest favourite
Home in Winchester
4.93 out of 5 average rating, 55 reviews

Basecamp Retreat TimsFordLake

SharonRating, 5 stars1 week ago
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 don’t 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!!
Top guest favourite
Home in Trenton
4.97 out of 5 average rating, 148 reviews

Suite Retreat: Pool & Spa | Minutes to Chattanooga

MontanaRating, 5 stars4 days ago
Host was very welcoming and nice. Suite retreat was clean and spacious for a family of 4. Would definitely book again!
Superhost
Home in Winchester
5 out of 5 average rating, 3 reviews

SPF 44 Suntan @ Twin Creeks

RandallRating, 5 stars3 weeks ago
Very well furnished home. All the things you need to be comfortable in your stay. Very clean, like new. Jillian was very easy to work with and prompt in communicating.
Guest favourite
Home in Flintstone
4.91 out of 5 average rating, 114 reviews

Chatt Vistas Oasis-3bdrm-5m to TN-PoolDeckBBQFireP

NayaRating, 5 stars2 weeks ago
Loved the Airbnb. Great for our family. The backyard, patio, and pool were fantastic! Worth it.

Weekly house rentals

Guest favourite
Home in Winchester
5 out of 5 average rating, 13 reviews

Location, location, location!

JonathanRating, 5 stars1 week ago
Amy was very helpful and accommodating. She was helpful and answered all my questions. I will be reserving it again for sure
Top guest favourite
Home in Tullahoma
5 out of 5 average rating, 33 reviews

Whiskey Trails Cottage

SuzanneRating, 5 stars1 week ago
Great place to stay! I was there because I had to teach at the TN Correctional Academy. It was a wonderful house... great location, quiet, private, beautifully decorated, great amenities, and easy check-in and out. I LOVED it! Highly recommend! Perfect for 1 person or a small family! ☺️☺️
Guest favourite
Home in Bridgeport
4.9 out of 5 average rating, 86 reviews

Little Red Cabin

EduardoRating, 5 stars1 week ago
Great location and great cabin. Peaceful and beautiful location. Highly recommend the Little Red Cabin.
Guest favourite
Home in Estill Springs
4.95 out of 5 average rating, 37 reviews

“The Country” Lake House w/ Private Dock

DevinRating, 5 stars3 days ago
We had an amazing stay at Trina’s Airbnb! My friends and I originally planned to attend Bonnaroo for the first time and unfortunately it was cancelled, which was a huge bummer. Everyone was feeling down and doubtful that we would enjoy the remainder of our stay, but we were very wrong. Although we strayed from our original plans, this Airbnb and the area we were staying in made this trip completely worth it! I don’t have one complaint and would book again in a heartbeat.
Top guest favourite
Home in Winchester
5 out of 5 average rating, 15 reviews

Lakeshore Modern- steps to water

CallieRating, 5 stars7 months ago
If I could give this place more than 5 stars I absolutely would. This home was absolutely amazing and I would recommend it to anyone!! The night sky was stunning!! I booked this house to hold off my bridesmaids the night before my wedding. We all got around and told stories about how each one knew me and why I love them. We sat at the table and made our bouquets it was so much fun!! The host has been absolute fantastic!! She helped me find my girls glasses and ones of their fiancé’s rings. She has been absolute amazing during this whole trip. I would always recommend staying with her!!
Top guest favourite
Home in Lynchburg
5 out of 5 average rating, 67 reviews

Cedar Cabin of Lynchburg - 3 miles to Jack Daniels

Jami LynnRating, 5 stars1 month ago
Beautiful clean home!! Was perfect for our stay. We wish we could have stayed longer!
Superhost
Home in Winchester
4.85 out of 5 average rating, 41 reviews

Gorgeous lake home in Twin Creeks with Lake View

ReginaRating, 5 stars8 months ago
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!
Top guest favourite
Home in Winchester
5 out of 5 average rating, 15 reviews

Tennessee Pearl: lakefront-amazing views-lake toys

Christy E.Rating, 5 stars2 weeks ago
The home was absolutely beautiful, perfectly decorated, and well layed out design. We felt right at home the entire time and absolutely loved all the included amenities! Thank you again for sharing your home with us!

Private house rentals

Top guest favourite
Home in Tullahoma
5 out of 5 average rating, 94 reviews

Lakeside Retreat at The Reserve w/ Golf Cart

RandiRating, 5 stars1 week ago
Mathew’s place was perfect for our stay for my grandfather’s 83rd birthday. The house is so comfortable and has everything you could ever need. The back porch was a favorite spot for morning coffee and evening drinks. Everything was perfect!
Top guest favourite
Home in Monteagle
5 out of 5 average rating, 19 reviews

Haven Forest House

NicholasRating, 5 stars1 week ago
Amazing property. Everything was exactly how it was described in the listing, or better. Hosts were very responsive and friendly. Our stay was peaceful and quiet with an incredible view.
Guest favourite
Home in Normandy
5 out of 5 average rating, 6 reviews

New Farmhouse Near The Lake

MiaRating, 5 stars2 weeks ago
The house was exactly as listed. Super responsive host that was willing to answer all of my questions and verify information quickly. Very beautiful new construction home. Although you feel like you are in the middle of nowhere, amenities are a short drive away. I would definitely stay here again. My only suggestion would be to add blinds or curtains downstairs. Someone being able to see directly in the house feels strange when you’re in an unfamiliar setting. Also just to note, the mattresses are a bit on the firm side.
Top guest favourite
Home in Monteagle
5 out of 5 average rating, 36 reviews

Mountain Mist - HOT TUB & King bed w/ fire pit

AmandaRating, 5 stars1 week ago
Rachel was an AMAZING host! The home was beautiful and I highly recommend to anyone looking for a quiet place to relax!
Guest favourite
Home in Winchester
4.93 out of 5 average rating, 54 reviews

Tim’s Ford Lake 6BR private dock near Twin Creeks

KathyRating, 5 stars3 weeks ago
Our stay at Julie’s place was so good. All our family was there except one granddaughter. We had a great time on the water in spite of some rain. We rented a pontoon for Saturday and it was a hit for everyone. The house is well stocked and very spacious. It was helpful to have access to 2 kitchens. But just know there is nothing in the way of dishes or utensils downstairs. The game area was awesome and enjoyable for everyone. The downstairs bathroom needs a new shower because even though it’s clean it looks dirty. We had an issue with the AC when we got there and Julie jumped right on it and had someone there that night. (Even though she was in Italy!). We also found that the downstairs patio area had not been cleaned in a while and cushions were very dirty. We had to clean the two porches floors and cushions but I think no one had used the house for a while. Again she got someone there the next morning who power washed the patio and cushions outside. Julie is a great host.
Superhost
Home in Sewanee
4.79 out of 5 average rating, 19 reviews

Forest Retreat: Poolside Bliss Close to Campus

SamanthaRating, 5 stars1 month ago
A lovely stay, beautiful, peaceful, perfect
Top guest favourite
Home in Tullahoma
4.98 out of 5 average rating, 60 reviews

Beautiful cottage next to Tims Ford Lake

LaurelRating, 5 stars3 days ago
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!
Top guest favourite
Home in Winchester
5 out of 5 average rating, 14 reviews

Lakeside Serenity: Cove Retreat

ElaineRating, 5 stars1 week ago
I felt like a welcomed guest from the minute I walked in. The home was spotless and smelled so clean and fresh. I have rented in Tennessee for the last 15 summers and have never rented a place that had so many extras (smores-popcorn- coffee pods-toiletries-kitchen supplies-etc. .Phil checked in to make sure everything was O:K. It is an absolute 5 Star !!!!

Quick stats about house rentals in Winchester

  • Total rentals

    80 properties

  • Nightly prices starting at

    ₹6,074 before taxes and fees

  • Total number of reviews

    2.3K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    40 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Tennessee
  4. Franklin County
  5. Winchester
  6. House rentals