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Apartments under $2,000 for Rent in Winchester, VA

184 Rentals
.
  1. Building Photo - 23 Montague Cir
    4 BEDS, 2 BATHS
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    23 Montague Cir

    23 Montague Cir, Winchester, VA 22601
  2. Building Photo - 2069 Cidermill Ln
    3 BEDS, 2.5 BATHS
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    2069 Cidermill Ln

    2069 Cidermill Ln, Winchester, VA 22601
  3. 2 BEDS, 1 BATH
    $1,450
    Total Monthly Price Total Monthly Price New
    Base Rent$1,450
    Required Monthly FeesNone
    Total Monthly Price$1,450

    540 Monticello St Unit 4

    540 Monticello St, Winchester, VA 22601
  4. 1 BED, 1 BATH
    $1,300
    Total Monthly Price Total Monthly Price New
    Base Rent$1,300
    Required Monthly FeesNone
    Total Monthly Price$1,300

    116 N Indian Alley Unit 101

    116 N Indian Alley, Winchester, VA 22601
  5. 1 BED, 1 BATH
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    115 S Loudoun St

    115 S Loudoun St, Winchester, VA 22601
  6. 3 BEDS, 1.5 BATHS
    $1,600
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600
    Required Monthly FeesNone
    Total Monthly Price$1,600

    8 W Monmouth St

    8 W Monmouth St, Winchester, VA 22601
  7. 1 BED, 1 BATH
    $900
    Total Monthly Price Total Monthly Price New
    Base Rent$900
    Required Monthly FeesNone
    Total Monthly Price$900

    4 W Cork St Unit 1

    4 W Cork St, Winchester, VA 22601
  8. 3 BEDS, 1 BATH
    $1,749
    Total Monthly Price Total Monthly Price New
    Base Rent$1,749
    Required Monthly FeesNone
    Total Monthly Price$1,749

    265 Opequon Ave

    265 Opequon Ave, Winchester, VA 22601
  9. 3 BEDS, 2 BATHS
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    103 Sutton Ct

    103 Sutton Ct, Winchester, VA 22601
  10. 3 BEDS, 1 BATH
    $1,900
    Total Monthly Price Total Monthly Price New
    Base Rent$1,900
    Required Monthly FeesNone
    Total Monthly Price$1,900

    2325 Wilson Blvd

    2325 Wilson Blvd, Winchester, VA 22601
  11. 2 BEDS, 2 BATHS
    $1,950
    Total Monthly Price Total Monthly Price New
    Base Rent$1,950
    Required Monthly FeesNone
    Total Monthly Price$1,950

    515 Amherst St

    515 Amherst St, Winchester, VA 22601
  12. 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

    1016 Franklin St

    1016 Franklin St, Winchester, VA 22601
  13. 2 BEDS, 2.5 BATHS
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    104 Eastside Ln

    104 Eastside Ln, Winchester, VA 22602
  14. 2 BEDS, 1 BATH
    $1,425
    Total Monthly Price Total Monthly Price New
    Base Rent$1,425
    Required Monthly FeesNone
    Total Monthly Price$1,425

    131 S Purcell Ave

    131 S Purcell Ave, Winchester, VA 22601
  15. 2 BEDS, 1 BATH
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    380 Shawnee Ave

    380 Shawnee Ave, Winchester, VA 22601
  16. 3 BEDS, 2 BATHS
    $1,995
    Total Monthly Price Total Monthly Price New
    Base Rent$1,995
    Required Monthly FeesNone
    Total Monthly Price$1,995

    101 Brier Rabbit Ct

    101 Brier Rabbit Ct, Winchester, VA 22602
  17. 1 BED, 1 BATH
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    3548 N Frederick Pike

    3548 N Frederick Pike, Winchester, VA 22603
  18. 3 BEDS, 2.5 BATHS
    $1,975
    Total Monthly Price Total Monthly Price New
    Base Rent$1,975
    Required Monthly FeesNone
    Total Monthly Price$1,975

    2040 Stoneleigh Dr

    2040 Stoneleigh Dr, Winchester, VA 22601
  19. 3 BEDS, 2 BATHS
    $1,850
    Total Monthly Price Total Monthly Price New
    Base Rent$1,850
    Required Monthly FeesNone
    Total Monthly Price$1,850

    553 Highland Ave

    553 Highland Ave, Winchester, VA 22601
  20. 2 BEDS, 2 BATHS
    $1,575
    Total Monthly Price Total Monthly Price New
    Base Rent$1,575
    Required Monthly FeesNone
    Total Monthly Price$1,575

    26 E Pall Mall St

    26 E Pall Mall St, Winchester, VA 22601
  21. 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

    204 E Whitlock Ave

    204 E Whitlock Ave, Winchester, VA 22601
  22. 3 BEDS, 1 BATH
    $1,495
    Total Monthly Price Total Monthly Price New
    Base Rent$1,495
    Required Monthly FeesNone
    Total Monthly Price$1,495

    230 E Whitlock Ave

    230 E Whitlock Ave, Winchester, VA 22601
  23. 2 BEDS, 1 BATH
    $1,950
    Total Monthly Price Total Monthly Price New
    Base Rent$1,950
    Required Monthly FeesNone
    Total Monthly Price$1,950

    126 N Braddock St Unit 202

    126 N Braddock St, Winchester, VA 22601
  24. 1 BED, 1 BATH
    $1,750
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750
    Required Monthly FeesNone
    Total Monthly Price$1,750

    517 Amherst St

    517 Amherst St, Winchester, VA 22601
  25. 1 BED, 1 BATH
    $1,600
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600
    Required Monthly FeesNone
    Total Monthly Price$1,600

    519 Amherst St Unit 202

    519 Amherst St, Winchester, VA 22601
  26. 1 BED, 1 BATH
    $1,750
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750
    Required Monthly FeesNone
    Total Monthly Price$1,750

    519 Amherst St Unit 201

    519 Amherst St, Winchester, VA 22601
  27. 2 BEDS, 1 BATH
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    217 Bridgewater Dr

    217 Bridgewater Dr, Stephens City, VA 22655
  28. 3 BEDS, 2 BATHS
    $1,995
    Total Monthly Price Total Monthly Price New
    Base Rent$1,995
    Required Monthly FeesNone
    Total Monthly Price$1,995

    100 Deer Hill Ct

    100 Deer Hill Ct, Stephens City, VA 22655
  29. 3 BEDS, 1.5 BATHS
    $1,750
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750
    Required Monthly FeesNone
    Total Monthly Price$1,750

    202 Carroll Dr

    202 Carroll Dr, Stephens City, VA 22655
  30. 3 BEDS, 1 BATH
    $1,750
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750
    Required Monthly FeesNone
    Total Monthly Price$1,750

    573 Fairfax Pike

    573 Fairfax Pike, Stephens City, VA 22655
  31. 3 BEDS, 1.5 BATHS
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    140 Lexington Ct

    140 Lexington Ct, Stephens City, VA 22655
  32. Building Photo - 129 Holiday Dr
    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

    129 Holiday Dr Unit 1

    129 Holiday Dr, Winchester, VA 22601
  33. Building Photo - 606 Tudor Dr
    2 BEDS, 1.5 BATHS
    $1,550
    Total Monthly Price Total Monthly Price New
    Base Rent$1,550
    Required Monthly FeesNone
    Total Monthly Price$1,550

    606 Tudor Dr

    606 Tudor Dr, Winchester, VA 22603
  34. 3 BEDS, 1 BATH
    $1,395
    Total Monthly Price Total Monthly Price New
    Base Rent$1,395
    Required Monthly FeesNone
    Total Monthly Price$1,395

    1001 S Cameron St

    1001 S Cameron St, Winchester, VA 22601
  35. 3 BEDS, 1.5 BATHS
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    212 Hunter Run Rd

    212 Hunter Run Rd, Winchester, VA 22602
  36. 3 BEDS, 1.5 BATHS
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    304 Shenandoah Ave

    304 Shenandoah Ave, Winchester, VA 22601
  37. 3 BEDS, 1 BATH
    $1,695
    Total Monthly Price Total Monthly Price New
    Base Rent$1,695
    Required Monthly FeesNone
    Total Monthly Price$1,695

    668 Virginia Ave

    668 Virginia Ave, Winchester, VA 22601
  38. 2 BEDS, 1 BATH
    $1,395
    Total Monthly Price Total Monthly Price New
    Base Rent$1,395
    Required Monthly FeesNone
    Total Monthly Price$1,395

    305 S Kent St

    305 S Kent St, Winchester, VA 22601
  39. 2 BEDS, 1 BATH
    $1,495
    Total Monthly Price Total Monthly Price New
    Base Rent$1,495
    Required Monthly FeesNone
    Total Monthly Price$1,495

    307 Emily Ln

    307 Emily Ln, Winchester, VA 22602
  40. 2 BEDS, 1 BATH
    $1,495
    Total Monthly Price Total Monthly Price New
    Base Rent$1,495
    Required Monthly FeesNone
    Total Monthly Price$1,495

    502 N Loudoun St

    502 N Loudoun St, Winchester, VA 22601
  41. 3 BEDS, 1.5 BATHS
    $1,495
    Total Monthly Price Total Monthly Price New
    Base Rent$1,495
    Required Monthly FeesNone
    Total Monthly Price$1,495

    1110 Allen Dr

    1110 Allen Dr, Winchester, VA 22601
  42. 3 BEDS, 2.5 BATHS
    $1,895
    Total Monthly Price Total Monthly Price New
    Base Rent$1,895
    Required Monthly FeesNone
    Total Monthly Price$1,895

    304 Emily Ln

    304 Emily Ln, Winchester, VA 22602
Showing 42 of 93 results, Page 2 of 3

Winchester at a Glance

Average Rent

$1,382
(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

Renting in Winchester

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winchester

(For 1 bedroom apartments)

Education

GreatSchools Rating
James Wood High School

Public High School

Public
Grades 9-12
1,470 Students
GreatSchools Rating
James Wood High

Public High School

Public
Grades 9-12
1,437 Students
GreatSchools Rating
Millbrook High School

Public High School

Public
Grades 9-12
1,553 Students
GreatSchools Rating
John Handley High School

Public High School

Public
Grades 9-12
1,361 Students
GreatSchools Rating
Admiral Richard E. Byrd Middle

Public Middle School

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

Public Middle School

Public
Grades 6-8
804 Students
GreatSchools Rating
Daniel Morgan Middle School

Public Middle School

Public
Grades 6-8
642 Students
GreatSchools Rating
James Wood Middle

Public Middle School

Public
Grades 6-8
803 Students
GreatSchools Rating
James Wood Middle School

Public Middle School

Public
Grades 6-8
803 Students

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

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