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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 2 Condo Rentals in Winchester with updated reviews, rates, and availability.

lake front 2 br condo close to bsu
Exterior

lake front 2 br condo close to bsu

9.4 out of 10, Exceptional, (42)
"If mattresses are replaced, rating would be Excellent!"
lake front 2 br condo close to bsu
Updated condo in the heart of Historic District with patio, streaming, fast WiFi
TV

Updated condo in the heart of Historic District with patio, streaming, fast WiFi

10.0 out of 10, Exceptional, (13)
"I will be staying again!"
The price is AED 430
AED 1,177 total
includes taxes & fees
5 May - 6 May
Updated condo in the heart of Historic District with patio, streaming, fast WiFi
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
Sign in
Sign up, it's free

Other property types in Winchester

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Outdoor dining

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

9.8 out of 10, Exceptional, (182)
"Plenty of room for our 25 that stayed. The pool is wonderful. Very clean and communication is excellent. This was our second stay and will do it again. Thank you Ted"
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Sport court

Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

10.0 out of 10, Exceptional, (186)
"An awesome place to stay with a large group. The indoor pickleball was a huge hit!!"
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
Living area

Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

9.8 out of 10, Exceptional, (7)
"The atmosphere and views are stunning. The home is spacious for families. We enjoyed our stay. "
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
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?
Expedia makes it a cinch to find your dream condo in Winchester. On the lookout for a luxury escape? Find your way to the filters to search for properties that have a 5-star rating. If you’re sticking to a budget, click on how much you’re willing to spend and then browse our incredible deals. We’ll help you find the perfect stay whatever your getaway looks like.
How can I find cheap condos in Winchester?
Expedia can help you locate cheap condos in Winchester. To find the perfect stay in just a few clicks, simply use our convenient filter tool to tailor your search results by star rating, budget and amenities.