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Our top choices for Winchester condo rentals

2.5 star property
8.0 out of 10, Very Good, (643 reviews)
"Really great place to stay. "
United States
Barbara
$88 nightly
The price is $97
Mar 23 - Mar 24
Total with taxes and fees
Black Bear Lodge Motel
2.0 star property
7.6 out of 10, Good, (1,002 reviews)
"Staff was extremely friendly at check in and check out, and we had a fine stay for a quick overnight "
United States
Laura
$54 nightly
The price is $60
Mar 25 - Mar 26
Total with taxes and fees
Super 8 by Wyndham Richmond
3.0 star property
9.4 out of 10, Exceptional, (2,179 reviews)
"Very clean and well kept and the breakfast was good"
United States
Manuel
$88 nightly
The price is $102
Mar 24 - Mar 25
Total with taxes and fees
Holiday Inn Express Lexington Horse Park Area by IHG

Motel in Winchester

Value Stay
2.0 star property
7.8 out of 10, Good, (132 reviews)
"Don't let the outside fool you. My room was super clean with brand new appliances..Fast and easy check in, staff was polite. If your looking for a cheap room just to lay your head down you can't go wrong here."
United States
Gary
$59 nightly
The price is $65
Mar 23 - Mar 24
Total with taxes and fees
Value Stay
2.5 star property
8.4 out of 10, Very Good, (1,001 reviews)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
$85 nightly
The price is $94
Mar 26 - Mar 27
Total with taxes and fees
Best Western Winchester Hotel
2.5 star property
7.2 out of 10, Good, (778 reviews)
"Great place for a reasonable price! "
United States
Whitney
$76 nightly
The price is $83
Mar 23 - Mar 24
Total with taxes and fees
Baymont by Wyndham Winchester
2.5 star property
9.2 out of 10, Wonderful, (552 reviews)
"Clean room, great hot fresh breakfast "
United States
Bob
$113 nightly
The price is $125
Mar 29 - Mar 30
Total with taxes and fees
Holiday Inn Express Lexington East - Winchester by IHG

Hotel in Winchester

Hampton Inn Winchester
2.5 star property
9.2 out of 10, Wonderful, (458 reviews)
"Enjoyed our stay."
United States
Randy
$114 nightly
The price is $126
Mar 29 - Mar 30
Total with taxes and fees
Hampton Inn Winchester

Hotel in Winchester

Comfort Inn Winchester
2.5 star property
7.0 out of 10, Good, (358 reviews)
"Very nice "
United States
Ronald
$69 nightly
The price is $76
Mar 29 - Mar 30
Total with taxes and fees
Comfort Inn Winchester
2.0 star property
6.4 out of 10, (592 reviews)
"Great stay"
United States
Walter
$62 nightly
The price is $69
Mar 25 - Mar 26
Total with taxes and fees
Red Roof Inn Winchester - Lexington East
3.5 star property
8.6 out of 10, Excellent, (1,826 reviews)
"WIfe and I had a great time. The rooms were clean and facilities were clean and inviting.."
United States
mike
$111 nightly
The price is $122
Apr 15 - Apr 16
Total with taxes and fees
Natural Bridge State Resort Park
2.5 star property
8.8 out of 10, Excellent, (593 reviews)
"Very clean, well maintained hotel. It’s close to lots of restaurants and right off the interstate."
United States
Todd
$95 nightly
The price is $105
Mar 29 - Mar 30
Total with taxes and fees
Holiday Inn Express & Suites Mt Sterling North by IHG
2.5 star property
7.8 out of 10, Good, (727 reviews)
"Room was very clean, check in was a breeze. "
United States
Emily
$78 nightly
The price is $86
Mar 29 - Mar 30
Total with taxes and fees
Comfort Inn & Suites Mount Sterling
3.0 star property
9.6 out of 10, Exceptional, (181 reviews)
"Clean room, friendly staff, decent breakfast "
United States
Kristi
$98 nightly
The price is $108
Apr 2 - Apr 3
Total with taxes and fees
Home2 Suites By Hilton Richmond, Ky

Hotel in Richmond

Hampton Inn Richmond
2.5 star property
9.2 out of 10, Wonderful, (1,002 reviews)
"Clean hotel with friendly staff. "
Canada
Susan
$98 nightly
The price is $108
Apr 5 - Apr 6
Total with taxes and fees
Hampton Inn Richmond

Hotel in Richmond

Quality Inn Richmond
2.5 star property
9.0 out of 10, Wonderful, (1,002 reviews)
"Clean room amd great staff"
United States
Randy
$99 nightly
The price is $109
Mar 23 - Mar 24
Total with taxes and fees
Quality Inn Richmond
2.5 star property
7.8 out of 10, Good, (351 reviews)
"Parking was good. Clean room. Staff friendly. The room was a little tight for a wheelchair but we managed. Overall it was great. "
United States
MIchelle
$102 nightly
The price is $112
Mar 23 - Mar 24
Total with taxes and fees
Best Western Paris Inn
2.0 star property
8.4 out of 10, Very Good, (1,001 reviews)
"Close to food and stores, clean room, good breakfast, friendly staff, good place to stay."
United States
Luis
$62 nightly
The price is $68
Mar 24 - Mar 25
Total with taxes and fees
Super 8 by Wyndham Georgetown
8.8 out of 10, Excellent, (1,158 reviews)
"A very well run hotel."
United States
Janice
$93 nightly
The price is $108
Mar 23 - Mar 24
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
9.0 out of 10, Wonderful, (1,006 reviews)
"I highly recommend this hotel. The rooms are very clean, staff is friendly and the breakfast is great!! "
United States
Joseph
$86 nightly
The price is $95
Mar 29 - Mar 30
Total with taxes and fees
Country Inn & Suites by Radisson, Georgetown, KY
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.
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Top Winchester Hotel Reviews

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
15,950
Accommodation
54 Condo Rentals
Lowest Price
$60
Highest Price
$126

Frequently asked questions

Why book your condo in Winchester with Expedia?
Getting away shouldn't be difficult, so if you're on the lookout for condos at an affordable rate, Expedia has got your back. Keep costs down and select something small and affordable, or splurge on a luxury condo and spoil your favorite people. Our search filters make it a breeze to find a property in Winchester that matches your needs.
How can I find cheap condos in Winchester?
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What is there to do in Winchester near my condo?
Once you've settled into your hotel, venture out and discover the fantastic things Winchester has on offer. Southwind Golf Course is a top attraction to add to your travel itinerary.

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