Search Condo Rentals in Winchester

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 1 Condo Rentals in Winchester with updated reviews, rates, and availability.

Newly renovated unit in downtown Maysville’s Entertainment District.

9.8 out of 10, Exceptional, (29)
"We absolutely loved this place! We walked everywhere, except for when we visited Augusta just down the road. Extremely clean and well furnished. Steve was available by text to answer any questions we had. Definitely will stay there again in the future."
Newly renovated unit in downtown Maysville’s Entertainment District.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Winchester

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

10.0 out of 10, Exceptional, (257)
"The cabin was wonderful and the host was great! We got about 14 inches of snow while there and the views were absolutely gorgeous. Had a few hiccups but the host was right there when we needed him. He was extremely friendly and helpful. Will definitely stay again!"
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .

10.0 out of 10, Exceptional, (127)
"The cabin is modern, cozy and clean and comes with everything you need!"
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .

The Cabin at 114 Main Street

9.6 out of 10, Exceptional, (34)
"Great location, extremely clean, clear directions, and cute outside area too. It was a terrific birthday weekend. We will definitely be back. "
The price is AED 511
AED 860 total
includes taxes & fees
1 Apr - 2 Apr
The Cabin at 114 Main Street
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Why book your condo in Winchester with Expedia?
We think that vacations shouldn’t be hard, so if you’re looking for condos at a competitive rate, Expedia has got you covered. Stick to the budget and stay in something cheap and cheerful, or splurge on a 5-star condo and spoil the ones you love most. Use our convenient search filters to find a stay in Winchester that suits your needs.
How can I find cheap condos in Winchester?
Expedia can help you narrow down your search for cheap condos in Winchester. To find your perfect stay in a couple of clicks, try out our handy filter tool to tailor your search results by star rating, amenities and budget.