Vacation rentals in Winchester
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Tiny home in Tullahoma
5.0 out of 5 average rating, 18 reviewsWhiskey Woods Retreat-Hot Tub
May 31 – Jun 7
Home in Winchester
4.97 out of 5 average rating, 34 reviewsBasecamp Retreat TimsFordLake
Mar 10 – 17
Farm stay in Shelbyville
4.98 out of 5 average rating, 65 reviewsCircle C Alpaca Farm - Entire apartment
Jul 27 – Aug 3
Cabin in Winchester
5.0 out of 5 average rating, 17 reviewsThe Cabins At Rivers Edge
May 24 – 31
Home in Decherd
5.0 out of 5 average rating, 59 reviewsNear The Caverns and Sewanee w/ Tesla / EV charger
Feb 14 – 21
Home in Winchester
5.0 out of 5 average rating, 17 reviewsLuxurious New Build LakeHouse Tim’s Ford 4BR4Bath
Nov 27 – Dec 4
Vacation home in Winchester
4.93 out of 5 average rating, 14 reviewsLakeside Laurel | Community Pool & Lake Access
Aug 18 – 25
Home in Winchester
4.97 out of 5 average rating, 74 reviewsBeautiful Tim's Ford Lake House (Sleeps 20)
Mar 26 – Apr 2
Quick stats about vacation rentals in Winchester
Total rentals
120 properties
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
2.4K reviews
Nightly prices starting at
R382 ZAR before taxes and fees
Frequently Asked Questions
Do cottage rentals in Winchester have free parking?
Absolutely! We offer over 10 cottage rentals with free parking in Winchester. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Winchester?
Four-legged friends are welcome in Winchester. Choose from more than 40 vacation rentals for guests traveling with pets.
How much does it cost to stay in cottage rentals in Winchester?
Experience the best of Winchester with our cottage rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Winchester have a kitchen?
Absolutely! We offer over 80 house rentals with a kitchen in Winchester. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Winchester?
Enhance your stay in our House Rentals with the most popular amenities: over 80 homes with air conditioning, over 80 homes with a kitchen, over 80 homes with free parking, over 80 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there Winchester vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Winchester, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Winchester have air conditioning?
Absolutely! We offer over 80 house rentals with air conditioning in Winchester. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Winchester?
Winchester has more than 110 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cottage rentals in Winchester have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Winchester. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Winchester?
Yes! Work meets play with ease at over 80 vacation rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.
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- Rentals with a fireplace Winchester
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