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Luxury Apartments for Rent in Winchester, VA

6 Rentals
.
  1. Building Photo - 104 S Loudoun St
    2 BEDS, 2 BATHS
    $2,200
    Total Monthly Price Total Monthly Price New
    Base Rent$2,200
    Required Monthly FeesNone
    Total Monthly Price$2,200

    104 S Loudoun St Unit 2

    104 S Loudoun St, Winchester, VA 22601
  2. Building Photo - 21 S Stewart St
    2 BEDS, 2 BATHS
    $2,200
    Total Monthly Price Total Monthly Price New
    Base Rent$2,200
    Required Monthly FeesNone
    Total Monthly Price$2,200

    21 S Stewart St Unit 4

    21 S Stewart St, Winchester, VA 22601
  3. 2 BEDS, 1 BATH
    $2,500
    Total Monthly Price Total Monthly Price New
    Base Rent$2,500
    Required Monthly FeesNone
    Total Monthly Price$2,500

    23 S Stewart St

    23 S Stewart St, Winchester, VA 22601
  4. Building Photo - 342 Fairmont Ave
    2 BEDS, 1 BATH
    $1,975
    Total Monthly Price Total Monthly Price New
    Base Rent$1,975
    Required Monthly FeesNone
    Total Monthly Price$1,975
         - 1 Month Lease

    342 Fairmont Ave Unit Apt 3

    342 Fairmont Ave, Winchester, VA 22601
    Apply
  5. Building Photo - 210 E Boscawen St
    2 BEDS, 2 BATHS
    $2,800
    Total Monthly Price Total Monthly Price New
    Base Rent$2,800
    Required Monthly FeesNone
    Total Monthly Price$2,800

    210 E Boscawen St Unit 202

    210 E Boscawen St, Winchester, VA 22601
  6. Building Photo - 516 Hollingsworth Dr
    2 BEDS, 1 BATH
    $2,100
    Total Monthly Price Total Monthly Price New
    Base Rent$2,100
    Required Monthly FeesNone
    Total Monthly Price$2,100

    516 Hollingsworth Dr

    516 Hollingsworth Dr, Winchester, VA 22601

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Winchester at a Glance

Average Rent

$1,308
(All bedrooms and property types)
Learn more about
Average Rent in Winchester
4

School Rating

out of 10 Rating
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Schools in Winchester
0

Some Transit

out of 100 TransitScore® Rating
Learn more about
Transportation in Winchester
39

Somewhat Bikeable

out of 100 BikeScore® Rating
Learn more about
Transportation in Winchester

Winchester, VA Apartments for Rent

Winchester is the northernmost independent city in Virginia and serves as the gateway to the scenic Shenandoah Valley, located just 75 miles from Washington, D.C. Those looking for apartments for rent in Winchester will discover everything from contemporary apartment communities near the expanding Meadow Branch district to historic properties in the city's established neighborhoods. The city is home to Shenandoah University and the Museum of the Shenandoah Valley, offering both educational opportunities and cultural attractions within its compact 10-square-mile area.

Renting in Winchester provides access to the Old Town Walking Mall along brick-paved Loudoun Street, where locally owned shops and cafes create a welcoming downtown atmosphere. The city's location along major transportation routes makes commuting to the Washington-Baltimore metro area manageable, while still offering lower rental costs than the surrounding region. Residents enjoy proximity to outdoor recreation in the Shenandoah Valley, annual events like the Shenandoah Apple Blossom Festival, and convenient shopping and dining options throughout the city's four wards. Winchester balances small-town living with access to employment centers in both Virginia and nearby West Virginia.

Renting in Winchester

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winchester

(For 1 bedroom apartments)

Getting Around Winchester

Transportation

48

Car-Dependent

out of 100 WalkScore® Rating
You might be able to get out and walk when living in this area. Some errands can be accomplished on foot, but for others you need a car.
39

Somewhat Bikeable

out of 100 BikeScore® Rating
You might be able to find places to ride your bike in this area, but you'll most likely want your car for most errands.
0

Minimal Transit

out of 100 TransitScore® Rating
You'll likely want a car when living in this area since it has few transit options.
Scores provided by Walk Scoreⓘ

Education

Private University
GreatSchools Rating
James Wood High

Public High School

Public
Grades 9-12
Students
GreatSchools Rating
John Handley High

Public High School

Public
Grades 9-12
Students
GreatSchools Rating
Millbrook High

Public High School

Public
Grades 9-12
Students
GreatSchools Rating
Daniel Morgan Middle

Public Middle School

Public
Grades 6-8
Students
GreatSchools Rating
Admiral Richard E. Byrd Middle

Public Middle School

Public
Grades 6-8
Students
GreatSchools Rating
James Wood Middle

Public Middle School

Public
Grades 6-8
Students
GreatSchools Rating
Frederick County Middle

Public Middle School

Public
Grades 6-8
Students

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

Apartments for Rent Near Winchester

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Winchester Apartments for Rent in Your Budget

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