House holiday rentals in Winchester

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Popular amenities for Winchester house rentals

House rentals with a pool

Top Guest favourite
Home in Winchester
5 out of 5 average rating, 32 reviews

Lakefront Haven on Tims Ford w/ Kayak and SUP

Mary LynRating, 5 stars1 month ago
We loved our stay here! Perfect spot for a girls weekend. The walk to the town square was an easy straight-shot - and we were so charmed by everything we found once we got there. We spent much of our time enjoying the screened in porch - so peaceful with lovely views! Kitchen was great and so were all the bedrooms and bathrooms!
Guest favourite
Home in Winchester
4.88 out of 5 average rating, 16 reviews

TC Easy Breeezee

LauraRating, 5 stars3 weeks ago
Lovely home, perfect for me and my toddler. He especially loved the bunk bed room. Plenty of towels, good coffee marker and nice bedding. Communication with the owner was pleasant and clear. I’d recommend and would stay at this home again.
Top Guest favourite
Home in Winchester
5 out of 5 average rating, 13 reviews

Lakeview Luxe | Lake Access + Pool

Jeff - PFS AmericasRating, 5 stars3 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!
Guest favourite
Home in Winchester
5 out of 5 average rating, 8 reviews

The Old Fashioned @ Twin Creeks - FREE BOAT & POOL

RichardRating, 5 stars5 months ago
Enjoyed time with friends and our little ones over new years. This was a great spot. Especially loved how many rooms had their own restroom and the upstairs area.
Guest favourite
Home in Winchester
5 out of 5 average rating, 11 reviews

Charming Barefoot Bay Bungalow

JenniferRating, 5 stars10 months ago
Beautiful place looks like brand new construction, great location, everything was done with excellence!
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.
Top Guest favourite
Home in Trenton
4.97 out of 5 average rating, 148 reviews

Suite Retreat: Pool & Spa | Minutes to Chattanooga

HollyRating, 5 stars4 days ago
My favorite Air BnB stay to date!!! Teresa and Mike were wonderful hosts! They provide everything you need to feel right at home. The location was great for visiting Chattanooga but far enough away from the city to have some peace and quiet! The pool and hot tub were well maintained and a pleasure to enjoy! I highly recommend and plan to stay again if we ever visit the area again!

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, 60 reviews

Luxury Living at Tim's Ford Lake, w/ Golf Cart

HarveyRating, 5 stars3 months ago
I recommend Steve’s place on your to do list in Tullahoma
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 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 Winchester
4.92 out of 5 average rating, 53 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
Guest favourite
Home in Estill Springs
4.94 out of 5 average rating, 36 reviews

“The Country” Lake House w/ Private Dock

KyleeRating, 5 stars6 months ago
This home was fantastic. We really appreciated the baby gear including safety gates, and the air hockey and football tables downstairs. The kitchen was well-equipped to cook for our crew of 7
Top Guest favourite
Home in Winchester
5 out of 5 average rating, 14 reviews

Lakeside Serenity: Cove Retreat

ElaineRating, 5 stars5 days 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 !!!!

Private house rentals

Top Guest favourite
Home in Tullahoma
5 out of 5 average rating, 36 reviews

New Cottage on Tims Ford Lake/Marina/Restaurant

KatieRating, 5 stars1 month ago
Kelly’s home was just as described and we had a wonderful vacation. She was even kind enough to send us recommendations for breakfast, dinner and even dessert! We would definitely stay again!
Top Guest favourite
Home in Tracy City
4.99 out of 5 average rating, 86 reviews

Little Green Cottage

MelissaRating, 5 stars1 week ago
My fiance and I stayed here for our minimoon with our two dogs. There was a fenced in backyard which was an amazing perk we didn’t know about before checking in. Ansley was very responsive and the cottage is SO cute. Definitely recommend!
Guest favourite
Home in Tracy City
5 out of 5 average rating, 22 reviews

The Little Lake House @The Retreat at Waters Edge

AlyssiaRating, 5 stars1 week ago
Went here for a chill weekend with friends for my birthday. The house is beautiful and well stocked with supplies. I only regret that we weren't able to sit by the fire pit due to storms. Nicky was a great host, her instructions answered any questions I had before I could ask them
Guest favourite
Home in Tracy City
4.95 out of 5 average rating, 21 reviews

Stay ON a Waterfall—13 acres! Bluffs, deck, views!

MarkRating, 5 stars1 month ago
Excellent host and home! Absolutely beautiful inside and out! My main love was the swinging bed! 2 nights spent and it was the best sleep ever!! Only thing I wish this property had was a hottub! The back decks are incredible, they would be even better with a hottub. Overall, a 5 out of 5 stars!!
Top Guest favourite
Home in Tullahoma
4.98 out of 5 average rating, 60 reviews

Beautiful cottage next to Tims Ford Lake

LaurelRating, 5 stars1 day 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 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!
Top Guest favourite
Home in Winchester
5 out of 5 average rating, 30 reviews

On Water w/ Private Dock, Entire Home, sleeps 14

NatalieRating, 5 stars1 week ago
We loved our stay! The house was clean and exactly as described. Chris was extremely responsive and I appreciated he offered an early check in without us even asking! It is in a neighborhood but felt extremely private. The dock is very private. I especially loved how close we were to twin lakes marina both by car and boat. We would absolutely stay again!
Top Guest favourite
Home in Tullahoma
5 out of 5 average rating, 5 reviews

The Cozy Cottage at Tim's Ford Lake (Sleeps 6)

FredRating, 5 stars5 months ago
I appreciated the smooth check-in to the last day I was there, Kim was always responsive and quick to resolve any issue I had. The place was clean and very comfortable with a fully functional kitchen was much valued. I would recommend staying at this great place and the friendly help with Kim. Thank you Fred K.

Quick stats about house rentals in Winchester

  • Total rentals

    80 properties

  • Nightly prices starting at

    $116 NZD 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

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