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

248 Rentals
.
  1. Building Photo - The Local
    Rent Special
    Rent Special
    |
    1 BED
    $1,700+
    2 BEDS
    $1,900+
    Plus Fees

    The Local

    230 Spring St, Winchester, VA 22601
    (434) 443-6043
  6. Interior Photo - Blue Ridge Apartments
    2 BEDS
    $1,420
    Total Monthly Price Total Monthly Price New
    Base Rent$1,375 - $1,700
    Required Monthly Fees$44
    Utilities & EssentialsVaries
    Total Monthly Price$1,419 - $1,744
         - 12 Month Lease

    Blue Ridge Apartments

    2260 Wilson Blvd, Winchester, VA 22601
    (888) 231-7146
  7. Interior Photo - Fay Street Apartments
    2 BEDS
    $1,572
    Total Monthly Price Total Monthly Price New
    Base Rent$1,545 - $1,795
    Required Monthly Fees$27
    Total Monthly Price$1,572 - $1,822

    Fay Street Apartments

    121 Fay St, Winchester, VA 22602
    (540) 306-4387
  8. 2 BEDS
    $1,747+
    3 BEDS
    $1,847+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,720 - $1,820
    Required Monthly Fees$27
    Total Monthly Price$1,747 - $1,847

    Fort Collier Terrace

    900-1024 N Braddock St, Winchester, VA 22601
    (540) 409-4434
  13. 3 BEDS
    $2,169
    Total Monthly Price Total Monthly Price New
    Base Rent$1,999 - $2,199
    Required Monthly Fees$170
    Total Monthly Price$2,169 - $2,369
         - 12 Month Lease

    West Wind Townhomes

    113 Holt Ct, Stephens City, VA 22655
    (540) 495-1621
  14. 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
  17. 2 BEDS
    $1,700
    Plus Fees

    CONTRAIL PARK

    749 Front Royal Pike, Winchester, VA 22602
  18. 1 BED
    $1,447+
    2 BEDS
    $1,549+
    3 BEDS
    $1,778+
    Plus Fees

    Peppertree VA

    221 Peppertree Ln, Winchester, VA 22601
  19. 2 BEDS
    $1,525+
    3 BEDS
    $1,800+
    Plus Fees

    PEMBERTON

    660 Pemberton Dr, Winchester, VA 22601
  22. 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
  24. 3 BEDS
    $1,735
    Plus Fees

    TASKER

    120 Caledon Ct, Stephens City, VA 22655
  25. 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
  26. 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
  27. 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
  28. 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

    228 Opequon Ave

    228 Opequon Ave, Winchester, VA 22601
  29. 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
  31. Building Photo - 102-107 Timberlake Terrace
    2 BEDS, 2 BATHS
    $1,600
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600
    Required Monthly FeesNone
    Total Monthly Price$1,600

    102-107 Timberlake Terrace Unit 7

    102-107 Timberlake Terrace, Stephens City, VA 22655
  32. Building Photo - 108-11-111 Timberlake Terrace
    2 BEDS, 2 BATHS
    $1,625
    Total Monthly Price Total Monthly Price New
    Base Rent$1,625
    Required Monthly FeesNone
    Total Monthly Price$1,625

    108-11-111 Timberlake Terrace Unit 11

    108-11-111 Timberlake Terrace, Stephens City, VA 22655
  33. Building Photo - 25 W Boscawen St
    1 BED, 1.5 BATHS
    $1,200
    Total Monthly Price Total Monthly Price New
    Base Rent$1,200
    Required Monthly FeesNone
    Total Monthly Price$1,200
         - 12 Month Lease

    25 W Boscawen St Unit 3

    25 W Boscawen St, Winchester, VA 22601
    Apply
  36. 2 BEDS, 1 BATH
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000
         - 12 Month Lease

    130 Montague Ave Unit Montague

    130 Montague Ave, Winchester, VA 22601
    Apply
  37. 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

    366 Valley Mill Rd

    366 Valley Mill Rd, Winchester, VA 22602
    Apply
  38. 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
         - 12 Month Lease

    210 N Kent St Unit A

    210 N Kent St, Winchester, VA 22601
    Apply
  39. 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
    Apply
  40. 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
  41. 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
         - 12 Month Lease

    24 Jackson Ave Unit 2

    24 Jackson Ave, Winchester, VA 22601
  42. Building Photo - 210 Stafford Dr
    3 BEDS, 1.5 BATHS
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000

    210 Stafford Dr

    210 Stafford Dr, Winchester, VA 22602
Showing 42 of 95 results, Page 1 of 3

Winchester at a Glance

Average Rent

$1,303
(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
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
GreatSchools Rating
Jordan Springs Elementary

Public Elementary School

Public
Grades K-5
Students

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

Apartments for Rent Near Winchester

Winchester Apartments for Rent in Your Budget

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