Photo by Betsy Wood

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
Wine Country Condo 1 bed 1 bath
Fridge, microwave, oven, dishwasher
Wine Country Condo 1 bed 1 bath
10.0 out of 10, Exceptional, (35)
"A neat and clean condo for good rest. It’s in a good location if you want to walk to groceries or Target. "
Wine Country Condo 1 bed 1 bath
Weekend Wine Getaway
Fridge, microwave, stovetop, dishwasher
Weekend Wine Getaway
10.0 out of 10, Exceptional, (2)
"Clean and comfortable. Quiet. Needs a cheese grater. We would def like to stay again."
Weekend Wine Getaway
Sangiovese By Avantstay Spectacular Estate w/ Pool, Hot Tub & Putting Green
Outdoor pool
Sangiovese By Avantstay Spectacular Estate w/ Pool, Hot Tub & Putting Green
3.5 star property
10.0 out of 10, Exceptional, (1)
"Loved everything about this place.Very spacious, lots of activities included. Especially the relaxing view from hill top. Master bedroom also had an amazing view. Highly recommend "
Sangiovese By Avantstay Spectacular Estate w/ Pool, Hot Tub & Putting Green
Hidden Paradise in the Heart of the City
Private kitchen
Hidden Paradise in the Heart of the City
Hidden Paradise in the Heart of the City
Wilson Creek Manor By Avantstay Sleeps 24! Amazing Estate w/ Pool & Game Room
Outdoor pool
Wilson Creek Manor By Avantstay Sleeps 24! Amazing Estate w/ Pool & Game Room
3.5 star property
Wilson Creek Manor By Avantstay Sleeps 24! Amazing Estate w/ Pool & Game Room
Beautiful Family Home Sleeps 6
Smart TV
Beautiful Family Home Sleeps 6
Beautiful Family Home Sleeps 6
Colina by Avantstay Secluded Mountain Top Oasis w/ Pool, Hot Tub & Putting Green!
Outdoor pool
Colina by Avantstay Secluded Mountain Top Oasis w/ Pool, Hot Tub & Putting Green!
3.5 star property
Colina by Avantstay Secluded Mountain Top Oasis w/ Pool, Hot Tub & Putting Green!
Room with private entrance private bathroom
Property grounds
Room with private entrance private bathroom
Room with private entrance private bathroom
Corporate 30 day rental
Fridge, microwave, stovetop, dishwasher
Corporate 30 day rental
Corporate 30 day rental
Condo
Property grounds
Condo
Condo
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

Retro Ranch Cottage 800sf Pool HotTub Pickleball
Pool
Retro Ranch Cottage 800sf Pool HotTub Pickleball
9.0 out of 10, Wonderful, (2)
"This cottage was amazing! Not only was it super clean but the decor was great and host was awesome! Very attentive and accommodating with any requests. The pool and outdoor area beautiful and everyone enjoyed there stay. We would definitely book another stay!"
Retro Ranch Cottage 800sf Pool HotTub Pickleball
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 breeze to find your ideal condo in Winchester. After an upmarket stay? Find your way to the filters to search for properties with a 5-star rating. If you have a fixed budget, select how much you want to spend and then check out our amazing deals. We’ll help you find the perfect pad whatever your trip looks like.
How can I find cheap condos in Winchester?
With Expedia’s helpful filter tool, booking cheap condos in Winchester couldn’t be simpler. To view accommodation that are very pocket friendly, narrow your search by amenities, star rating and budget.