Vacation rentals in Winchester

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Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

Twin Creeks Marina30 locals recommend
Piezan Pizzeria Italiano22 locals recommend
Walnut Hill Coffee Company28 locals recommend
Drafts & Watercrafts19 locals recommend
The Oldham17 locals recommend
SUNRISE (The Breakfast Place)8 locals recommend

Other great vacation rentals in Winchester

Guest favourite
Guesthouse in Lookout Valley
4.81 out of 5 average rating, 21 reviews

Chattanooga 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 reviews

Getaway 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 reviews

WILDFLOWER 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 reviews

Swordfish 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 reviews

Escape 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 reviews

Chattanooga 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 reviews

Sunset 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 reviews

Vantage 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

Destinations to explore

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