Note: Properties with the Total Monthly Price badge include all required fees. Tap the badge for more details.
-

Bedrooms

Bathrooms

Deals & Discount Filters
All Filters

Deals & Discounts

Price Range

–

Beds & Baths

Beds

Baths

Home Type

Pet Policy

Interior & Community Amenities

Speciality Housing

Keyword Search

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

184 Rentals
.
  1. Building Photo - 346 Gray Ave
    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

    346 Gray Ave

    346 Gray Ave, Winchester, VA 22601
  2. Building Photo - 2549 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

    2549 Bradford Ct

    2549 Bradford Ct, Winchester, VA 22601
  3. 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

    2533 Bradford Ct

    2533 Bradford Ct, Winchester, VA 22601
  4. 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

    308 Gainesboro Rd

    308 Gainesboro Rd, Winchester, VA 22603
  5. 2 BEDS, 1 BATH
    $1,150
    Total Monthly Price Total Monthly Price New
    Base Rent$1,150
    Required Monthly FeesNone
    Total Monthly Price$1,150

    22 Peyton St Unit Apt 3

    22 Peyton St, Winchester, VA 22601
  6. 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

    21-23 S. Stewart Street Unit 2102

    21-23-23 S Stewart St, Winchester, VA 22601
  7. 2 BEDS, 2 BATHS
    $1,995
    Total Monthly Price Total Monthly Price New
    Base Rent$1,995
    Required Monthly FeesNone
    Total Monthly Price$1,995

    2253 Papermill Rd

    2253 Papermill Rd, Winchester, VA 22601
  8. 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

    619 S Cameron St

    619 S Cameron St, Winchester, VA 22601
  9. 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
  10. 2 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

    1839 Henry Ave

    1839 Henry Ave, Winchester, VA 22601
  11. 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

    30 W Germain St

    30 W Germain St, Winchester, VA 22601
  12. 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

    26 Jackson Ave

    26 Jackson Ave, Winchester, VA 22601
  13. 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
  14. Exceptional Value
    2 BEDS
    $1,467
    Plus Fees - 12 Month Lease

    ZeroPak Apartments

    570 N Cameron St, Winchester, VA 22601
  15. 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

    890 Plymouth St

    890 Plymouth St, Stephens City, VA 22655
  16. 3 BEDS, 1 BATH
    $1,690
    Total Monthly Price Total Monthly Price New
    Base Rent$1,690
    Required Monthly FeesNone
    Total Monthly Price$1,690

    5340 Water St

    5340 Water St, Stephens City, VA 22655
Showing 42 of 101 results, Page 3 of 3

Can't find what you are looking for?

Clear All Filters

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

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

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.

tooltips


I would like to...
0 out of 400 characters
By clicking above, you agree we may pass along your info so this property or the property’s affiliates can email, call, text, or autodial you to follow up and for any purpose. You also agree to... By clicking above, you agree we may pass along your info so this property or the property’s affiliates can email, call, text, or autodial you to follow up and for any purpose. You also agree to Apartmentfinder.com’s Privacy Statement and Terms of Service. Consent is not a condition for services. Message and data rates may apply. Read More Read Less

Submitting Request

Thank You

Your email has been sent.

Learn about our ratings.