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

187 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
  4. Interior Photo - Fay Street Apartments
    2 BEDS
    $1,682+
    3 BEDS
    $1,852+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,655 - $1,925
    Required Monthly Fees$27
    Total Monthly Price$1,682 - $1,952

    Fay Street Apartments

    121 Fay St, Winchester, VA 22602
    (540) 306-4387
  5. Good Value
    2 BEDS
    $1,677+
    3 BEDS
    $1,782+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650 - $1,820
    Required Monthly Fees$27
    Total Monthly Price$1,677 - $1,847

    Fort Collier Terrace

    900-1024 N Braddock St, Winchester, VA 22601
    (540) 409-4434
  8. Interior Photo - Blue Ridge Apartments
    Good Value
    2 BEDS
    $1,495
    Total Monthly Price Total Monthly Price New
    Base Rent$1,450 - $1,625
    Required Monthly Fees$45
    Total Monthly Price$1,495 - $1,670
         - 12 Month Lease

    Blue Ridge Apartments

    2260 Wilson Blvd, Winchester, VA 22601
    (888) 231-7146
  11. 3 BEDS, 1 BATH
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500
         - 12 Month Lease

    218 Bufflick Rd

    218 Bufflick Rd, Winchester, VA 22602
    Apply
  12. Building Photo - 148 N Loudoun St
    Good Value
    1 BED
    $1,600+
    2 BEDS
    $1,800+
    Plus Fees

    148 N Loudoun St

    148 N Loudoun St, Winchester, VA 22601
  13. Facade - CONTRAIL PARK
    2 BEDS
    $1,780
    Plus Fees

    CONTRAIL PARK

    749 Front Royal Pike, Winchester, VA 22602
  14. Good Value
    1 BED
    $1,570+
    2 BEDS
    $1,619+
    3 BEDS
    $1,754+
    Plus Fees

    Peppertree VA

    221 Peppertree Ln, Winchester, VA 22601
  15. 2 BEDS
    $1,450+
    3 BEDS
    $1,850+
    Plus Fees

    PEMBERTON

    660 Pemberton Dr, Winchester, VA 22601
  17. 2 BEDS
    $1,469+
    3 BEDS
    $1,685+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,424 - $1,643
    Required Monthly Fees$45
    Total Monthly Price$1,469 - $1,688
         - 12 Month Lease

    Preston Place

    124 Castlebridge Ct, Winchester, VA 22602
  21. 2 BEDS
    $1,650
    Plus Fees

    TASKER

    120 Caledon Ct, Stephens City, VA 22655
  24. Building Photo - 23 Taft Ave
    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

    23 Taft Ave Unit 3

    23 Taft Ave, Winchester, VA 22601
  25. 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
  26. 1 BED, 1 BATH
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    619 S Cameron St Unit 2

    619 S Cameron St, Winchester, VA 22601
  27. 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

    2256 Roosevelt Blvd

    2256 Roosevelt Blvd, Winchester, VA 22601
  28. 1 BED, 1 BATH
    $1,550
    Total Monthly Price Total Monthly Price New
    Base Rent$1,550
    Required Monthly FeesNone
    Total Monthly Price$1,550

    550 N Loudoun St Unit 1

    550 N Loudoun St, Winchester, VA 22601
  29. Building Photo - 21 S Stewart St
    2 BEDS, 2 BATHS
    $1,900
    Total Monthly Price Total Monthly Price New
    Base Rent$1,900
    Required Monthly FeesNone
    Total Monthly Price$1,900

    21 S Stewart St Unit 4

    21 S Stewart St, Winchester, VA 22601
  33. Building Photo - 21 N Braddock St
    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
         - 12 Month Lease

    21 N Braddock St

    21 N Braddock St, Winchester, VA 22601
    Apply
  34. Building Photo - 13 E North Ave
    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
         - 12 Month Lease

    13 E North Ave Unit 1

    13 E North Ave, Winchester, VA 22601
    Apply
  35. 2 BEDS, 1 BATH
    $1,100
    Total Monthly Price Total Monthly Price New
    Base Rent$1,100
    Required Monthly FeesNone
    Total Monthly Price$1,100
         - 12 Month Lease

    5 E Pall Mall St Unit 7

    5 E Pall Mall St, Winchester, VA 22601
    Apply
  36. 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

    318 S Cameron St Unit Apt A

    318 S Cameron St, Winchester, VA 22601
    Apply
  37. 1 BED, 1 BATH
    $1,900
    Total Monthly Price Total Monthly Price New
    Base Rent$1,900
    Required Monthly FeesNone
    Total Monthly Price$1,900
         - 1 Month Lease

    2971 Valley Ave Unit 101

    2971 Valley Ave, Winchester, VA 22601
    Apply
  38. 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

    178 Broad Ave

    178 Broad Ave, Winchester, VA 22602
    Apply
  41. 1 BED, 1 BATH
    $1,100
    Total Monthly Price Total Monthly Price New
    Base Rent$1,100
    Required Monthly FeesNone
    Total Monthly Price$1,100
         - 13 Month Lease

    5195 Main St Unit 3

    5195 Main St, Stephens City, VA 22655
    Apply
  42. 1 BED, 1 BATH
    $1,395
    Total Monthly Price Total Monthly Price New
    Base Rent$1,395
    Required Monthly FeesNone
    Total Monthly Price$1,395
         - 12 Month Lease

    2640 Valley Ave Unit All Utilities Included

    2640 Valley Ave, Winchester, VA 22601
Showing 42 of 104 results, Page 1 of 3

Winchester at a Glance

Average Rent

$1,358
(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
1,437 Students
GreatSchools Rating
James Wood High School

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.

Apartments for Rent Near Winchester

Winchester Apartments for Rent in Your Budget

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