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Cheap Apartments for Rent in Winchester, VA

341 Rentals
  1. Interior Photo - Fay Street Apartments
    1 BED
    $1,222+
    2 BEDS
    $1,572+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,195 - $1,795
    Required Monthly Fees$27
    Total Monthly Price$1,222 - $1,722

    Fay Street Apartments

    121 Fay St, Winchester, VA 22602
    (540) 306-4387
  2. Building Photo - 434 N Kent St
    2 BEDS, 1 BATH
    $1,200
    Total Monthly Price Total Monthly Price New
    Base Rent$1,200
    Required Monthly FeesNone
    Total Monthly Price$1,200

    434 N Kent St Unit #4

    434 N Kent St, Winchester, VA 22601
  3. Building Photo - 434 N Kent St
    2 BEDS, 1 BATH
    $1,200
    Total Monthly Price Total Monthly Price New
    Base Rent$1,200
    Required Monthly FeesNone
    Total Monthly Price$1,200

    434 N Kent St Unit #3

    434 N Kent St, Winchester, VA 22601
  4. Building Photo - 24 Jackson Ave
    2 BEDS, 1 BATH
    $1,250
    Total Monthly Price Total Monthly Price New
    Base Rent$1,250
    Required Monthly FeesNone
    Total Monthly Price$1,250

    24 Jackson Ave Unit APT 2

    24 Jackson Ave, Winchester, VA 22601
  5. Building Photo - 652 Virginia Ave
    2 BEDS, 1 BATH
    $1,295
    Total Monthly Price Total Monthly Price New
    Base Rent$1,295
    Required Monthly FeesNone
    Total Monthly Price$1,295

    652 Virginia Ave

    652 Virginia Ave, Winchester, VA 22601
  6. Building Photo - 11 E Pall Mall St
    2 BEDS, 1 BATH
    $1,300
    Total Monthly Price Total Monthly Price New
    Base Rent$1,300
    Required Monthly FeesNone
    Total Monthly Price$1,300
    - 12 Month Lease

    11 E Pall Mall St

    11 E Pall Mall St, Winchester, VA 22601
  7. Building Photo - 1114 Allen Dr
    2 BEDS, 1 BATH
    $1,300
    Total Monthly Price Total Monthly Price New
    Base Rent$1,300
    Required Monthly FeesNone
    Total Monthly Price$1,300

    1114 Allen Dr

    1114 Allen Dr, Winchester, VA 22601
  8. Building Photo - 233 Kern St
    2 BEDS, 1 BATH
    $1,350
    Total Monthly Price Total Monthly Price New
    Base Rent$1,350
    Required Monthly FeesNone
    Total Monthly Price$1,350

    233 Kern St

    233 Kern St, Winchester, VA 22601
  9. Building Photo - Peppertree VA
    Good Value
    1 BED
    $1,406+
    2 BEDS
    $1,550+
    3 BEDS
    $1,721+
    Plus Fees

    Peppertree VA

    221 Peppertree Ln, Winchester, VA 22601
  10. Building Photo - 2555 Bradford Ct
    1 BED, 1 BATH
    $1,425
    Total Monthly Price Total Monthly Price New
    Base Rent$1,425
    Required Monthly FeesNone
    Total Monthly Price$1,425

    2555 Bradford Ct

    2555 Bradford Ct, Winchester, VA 22601
  11. Building Photo - Preston Place
    2 BEDS
    $1,476+
    3 BEDS
    $1,690+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,431 - $1,650
    Required Monthly Fees$45
    Total Monthly Price$1,476 - $1,695
    - 12 Month Lease

    Preston Place

    124 Castlebridge Ct, Winchester, VA 22602
  12. Interior Photo - Blue Ridge Apartments
    Good Value
    2 BEDS
    $1,495
    Total Monthly Price Total Monthly Price New
    Base Rent$1,450 - $1,700
    Required Monthly Fees$45
    Utilities & EssentialsVaries
    Total Monthly Price$1,495 - $1,745
    - 12 Month Lease

    Blue Ridge Apartments

    2260 Wilson Blvd, Winchester, VA 22601
    (888) 231-7146
  13. Building Photo - 11 Taft Ave
    2 BEDS, 2 BATHS
    $1,450
    Total Monthly Price Total Monthly Price New
    Base Rent$1,450
    Required Monthly FeesNone
    Total Monthly Price$1,450

    11 Taft Ave

    11 Taft Ave, Winchester, VA 22601
  14. Building Photo - 104 Waterford Ln
    2 BEDS, 1 BATH
    $1,475
    Total Monthly Price Total Monthly Price New
    Base Rent$1,475
    Required Monthly FeesNone
    Total Monthly Price$1,475

    104 Waterford Ln

    104 Waterford Ln, Winchester, VA 22602
  15. Building Photo - 2550 Bradford Ct
    1 BED, 1 BATH
    $1,495
    Total Monthly Price Total Monthly Price New
    Base Rent$1,495
    Required Monthly FeesNone
    Total Monthly Price$1,495

    2550 Bradford Ct

    2550 Bradford Ct, Winchester, VA 22601
  16. Building Photo - 3107 Shawnee Dr
    2 BEDS, 1.5 BATHS
    $1,499
    Total Monthly Price Total Monthly Price New
    Base Rent$1,499
    Required Monthly FeesNone
    Total Monthly Price$1,499

    3107 Shawnee Dr Unit 11

    3107 Shawnee Dr, Winchester, VA 22601
  17. Building Photo - 121 Taft Ave
    2 BEDS, 1 BATH
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    121 Taft Ave

    121 Taft Ave, Winchester, VA 22601
  18. Building Photo - 21 S Stewart St
    2 BEDS, 1 BATH
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    21 S Stewart St

    21 S Stewart St, Winchester, VA 22601
  19. Building Photo - 127-A Peyton Street
    2 BEDS, 1.5 BATHS
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500
    - 12 Month Lease

    127-A Peyton Street

    127-A Peyton Street, Winchester, VA 22601
  20. Building Photo - 544 Allston Cir
    2 BEDS, 1.5 BATHS
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    544 Allston Cir

    544 Allston Cir, Winchester, VA 22601
  21. Building Photo - 2 E Germain St
    2 BEDS, 1 BATH
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    2 E Germain St

    2 E Germain St, Winchester, VA 22601
  22. 2 BEDS, 1.5 BATHS
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    236 Nottoway Dr

    236 Nottoway Dr, Stephens City, VA 22655
  23. Building Photo - 3107 Shawnee Dr
    2 BEDS, 1.5 BATHS
    $1,549
    Total Monthly Price Total Monthly Price New
    Base Rent$1,549
    Required Monthly FeesNone
    Total Monthly Price$1,549

    3107 Shawnee Dr Unit 7

    3107 Shawnee Dr, Winchester, VA 22601
  24. Pemberton Village Exterior - PEMBERTON
    2 BEDS
    $1,575
    Plus Fees

    PEMBERTON

    660 Pemberton Dr, Winchester, VA 22601
  25. Cedar Hill - Exterior - CEDAR HILL APARTMENTS
    Rent Special
    2 BEDS
    $1,575+
    3 BEDS
    $1,650+
    Plus Fees

    CEDAR HILL APARTMENTS

    2250 Sofia Way, Winchester, VA 22601
  26. Building Photo - 609 Smithfield Ave
    2 BEDS, 1 BATH
    $1,575
    Total Monthly Price Total Monthly Price New
    Base Rent$1,575
    Required Monthly FeesNone
    Total Monthly Price$1,575

    609 Smithfield Ave

    609 Smithfield Ave, Winchester, VA 22601
  27. Building Photo - 102 Waterford Ln
    2 BEDS, 1 BATH
    $1,575
    Total Monthly Price Total Monthly Price New
    Base Rent$1,575
    Required Monthly FeesNone
    Total Monthly Price$1,575

    102 Waterford Ln

    102 Waterford Ln, Winchester, VA 22602
  28. 2 BEDS, 1.5 BATHS
    $1,595
    Total Monthly Price Total Monthly Price New
    Base Rent$1,595
    Required Monthly FeesNone
    Total Monthly Price$1,595

    205 Little River Dr

    205 Little River Dr, Winchester, VA 22602
  29. 2 BEDS, 2 BATHS
    $1,595
    Total Monthly Price Total Monthly Price New
    Base Rent$1,595
    Required Monthly FeesNone
    Total Monthly Price$1,595

    28 E Pall Mall St

    28 E Pall Mall St, Winchester, VA 22601
  30. Building Photo - 1061 Filbert St
    3 BEDS, 1 BATH
    $1,595
    Total Monthly Price Total Monthly Price New
    Base Rent$1,595
    Required Monthly FeesNone
    Total Monthly Price$1,595

    1061 Filbert St

    1061 Filbert St, Stephens City, VA 22655
  31. Building Photo - 3107 Shawnee Dr
    2 BEDS, 1.5 BATHS
    $1,599
    Total Monthly Price Total Monthly Price New
    Base Rent$1,599
    Required Monthly FeesNone
    Total Monthly Price$1,599

    3107 Shawnee Dr

    3107 Shawnee Dr, Winchester, VA 22601
  32. Building Photo - 148 N Loudoun St
    1 BED
    $1,600+
    2 BEDS
    $1,800+
    Plus Fees

    148 N Loudoun St

    148 N Loudoun St, Winchester, VA 22601
  33. Building Photo - 114 N Loudoun St
    STUDIO
    $1,600+
    1 BED
    $1,800+
    2 BEDS
    $2,600+
    Plus Fees - 1 Month Lease

    114 N Loudoun St

    114 N Loudoun St, Winchester, VA 22601
Showing 42 of 139 results, Page 1 of 4

Winchester at a Glance

Average Rent

$1,313
(All bedrooms and property types)
Learn more about
Average Rent in Winchester
4

School Rating

out of 10 Rating
Learn more about
Schools 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)

Education

Private University
GreatSchools Rating

Public High School

Public
Grades 9-12
1,437 Students
GreatSchools Rating

Public High School

Public
Grades 9-12
1,384 Students
GreatSchools Rating

Public High School

Public
Grades 9-12
1,516 Students
GreatSchools Rating

Public Middle School

Public
Grades 6-8
804 Students
GreatSchools Rating

Public Middle School

Public
Grades 6-8
613 Students
GreatSchools Rating

Public Middle School

Public
Grades 6-8
803 Students
GreatSchools Rating

Public Middle School

Public
Grades 6-8
751 Students
GreatSchools Rating

Public Elementary School

Public
Grades K-5
566 Students

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

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