
Vacation rentals in Winchester
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Top-rated vacation rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Guest favourite

Guesthouse in Lookout Valley
4.81 out of 5 average rating, 21 reviewsChattanooga pool vacation home!
MeghanRating, 5 stars1 month ago
Very nice and peaceful! Loved the hanging swings. Loved that it had some kids toys!
Superhost

Cottage in McMinnville
4.81 out of 5 average rating, 97 reviewsGetaway to heaven
JeffRating, 5 stars1 week ago
This was actually our 2nd stay in this home. It was very convenient to the venue we were going to. The home is always clean and it’s in a restful, peaceful area. We loved that they had added a little fire pit to enjoy the outdoors of an evening. I left my memory foam pillow by accident and Yennifer agreed to ship it to me! We will definitely stay there again if we have an occasion to be in McMinnville!
Guest favourite

Cabin in Bryant
4.98 out of 5 average rating, 89 reviewsWILDFLOWER CABIN, NO SUNDAY CHECK INS, HOT TUB
AshleyRating, 5 stars1 month ago
I love this cabin . It was just what me and my husband needed for our weekend getaway . We enjoyed the firepit ,swing and especially the hot tub !! Host was very responsive ! Thank you for letting us stay and can't wait to come back !!
Top guest favourite

Cottage in Tracy City
4.98 out of 5 average rating, 55 reviewsSwordfish Suite - Pup Shed Retreat
MorganRating, 5 stars1 month ago
We shot up to explore all of the hiking options in Tracy City and ended up loving the community of this AirBnB even more than the park! We kayaked for the first time, went fishing, played at the playground. The beds were so comfortable. Everything was beautifully decorated and felt like a home away from home. We didn’t bring our dogs this time but definitely will next time! Extremely dog friendly place! We loved all the little notes around the cottage and especially loved the owners food recommendations posted on the fridge. Would love to stay again ☺️
Top guest favourite

Tiny homes in Chattanooga
4.97 out of 5 average rating, 74 reviewsEscape Tiny Two
LisaRating, 5 stars3 weeks ago
I just love staying at Joan’s Tiny home! This is my 3rd stop. I actually plan my trips so that I can stay here . It’s a beautiful quiet setting…perfect for walks…it’s close to the city but feels like the country….The home has everything you need for a comfortable and pleasant stay. There are always little extras that are a nice touch. She’s responsive and kind. I look forward to my next stay already☺️
Guest favourite

Home in Lookout Valley
4.88 out of 5 average rating, 136 reviewsChattanooga River Retreat
Arlene De JagerRating, 5 stars3 weeks ago
Enjoyed our stay. Location was ideal for exploring Chattanooga. The house was very comfortable for our large family. The river setting was awesome and we took advantage of being able to hang out outdoors on the deck and around the fire pit. We earned points with our adult children by staying here.
Guest favourite

Cabin in Spencer
4.91 out of 5 average rating, 11 reviewsSunset Lodge at Rocky River Valley
HopeRating, 5 stars2 months ago
Beautiful home with everything you need. The home is a very comfortable & cozy place to stay. Views are amazing! Our big family enjoyed very much with plenty of room for gatherings and privacy for everyone. Lots of things to do. Highly recommend and Adrian is an excellent host. He did his best to accommodate our big family comfortably. Thank you so much Adrian!
Superhost

Home in Rising Fawn
4.85 out of 5 average rating, 80 reviewsVantage Point II
JulieRating, 5 stars4 weeks ago
The best thing about this house is the location! (The driveway is tricky though- take it slow!) The sunsets are fabulous and even though it’s on the main road, it’s really quiet and very private. Great BBQ! The house held our family reunion with people in and out at different times, so we really appreciated extra sheets available to change beds in between guests. Tons of towels, too! We’ve been here before and it has anything you’d want or need in a home away from home: the kitchen is well stocked, there’s a great laundry with starter soap, the beds are so comfy, the furniture also, and there are several seating areas, with tables inside and outside that can fit several people. The main area is huge and everyone can be in different spaces and still within site and talking distance. The only cons: the house is showing some wear, but it’s like a real home! It could use a few starter basics, ie salt and pepper, a bit of coffee, etc, but there were some-come with some supplies.
Quick stats about vacation rentals in Winchester
Total rentals
120 properties
Nightly prices starting at
$28 CAD before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
40 properties have a pool
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- Rentals with outdoor seating Winchester
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- Tennessee Aquarium
- Cloudland Canyon State Park
- Sweetens Cove Golf Club
- Monte Sano State Park
- The Ledges
- Black Creek Club
- Chattanooga Golf and Country Club
- Coolidge Park
- Creative Discovery Museum
- The Lookout Mountain Club
- Chattanooga Choo Choo
- Kyujo-mae Station
- Old Fort Golf Course
- National Medal of Honor Heritage Center
- Hunter Museum of American Art