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

Cheap Apartments for Rent in Downtown Winchester - Page 2

170 Rentals
.
  1. Building Photo - 1001 S Cameron St
    3 BEDS, 1 BATH
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    1001 S Cameron St

    1001 S Cameron St, Winchester, VA 22601
  7. Building Photo - 21 N Braddock St
    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
         - 12 Month Lease

    21 N Braddock St

    21 N Braddock St, Winchester, VA 22601
  9. Building Photo - 540 Bellview Ave
    3 BEDS, 1 BATH
    $1,850
    Total Monthly Price Total Monthly Price New
    Base Rent$1,850
    Required Monthly FeesNone
    Total Monthly Price$1,850

    540 Bellview Ave

    540 Bellview Ave, Winchester, VA 22601
  11. Building Photo - 1442 Greystone Terrace
    3 BEDS, 1.5 BATHS
    $1,925
    Total Monthly Price Total Monthly Price New
    Base Rent$1,925
    Required Monthly FeesNone
    Total Monthly Price$1,925

    1442 Greystone Terrace

    1442 Greystone Terrace, Winchester, VA 22601
  12. Building Photo - 6 E Cecil St
    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

    6 E Cecil St

    6 E Cecil St, Winchester, VA 22601
  13. Building Photo - 321 N Kent St
    3 BEDS, 1.5 BATHS
    $1,950
    Total Monthly Price Total Monthly Price New
    Base Rent$1,950
    Required Monthly FeesNone
    Total Monthly Price$1,950

    321 N Kent St

    321 N Kent St, Winchester, VA 22601
  14. 3 BEDS, 2.5 BATHS
    $1,995
    Total Monthly Price Total Monthly Price New
    Base Rent$1,995
    Required Monthly FeesNone
    Total Monthly Price$1,995

    916 S Loudoun St

    916 S Loudoun St, Winchester, VA 22601
  15. Building Photo - 342 Fairmont Ave
    2 BEDS, 1 BATH
    $2,100
    Total Monthly Price Total Monthly Price New
    Base Rent$2,100
    Required Monthly FeesNone
    Total Monthly Price$2,100
         - 1 Month Lease

    342 Fairmont Ave Unit Apt 3

    342 Fairmont Ave, Winchester, VA 22601
    Apply
  16. Building Photo - 318 Highland Ave
    3 BEDS, 2 BATHS
    $2,100
    Total Monthly Price Total Monthly Price New
    Base Rent$2,100
    Required Monthly FeesNone
    Total Monthly Price$2,100

    318 Highland Ave

    318 Highland Ave, Winchester, VA 22601
  17. Building Photo - 423 W Cork St
    3 BEDS, 1 BATH
    $2,100
    Total Monthly Price Total Monthly Price New
    Base Rent$2,100
    Required Monthly FeesNone
    Total Monthly Price$2,100

    423 W Cork St Unit B

    423 W Cork St, Winchester, VA 22601
  18. Building Photo - 122 Morningside Dr
    3 BEDS, 1 BATH
    $2,195
    Total Monthly Price Total Monthly Price New
    Base Rent$2,195
    Required Monthly FeesNone
    Total Monthly Price$2,195

    122 Morningside Dr

    122 Morningside Dr, Winchester, VA 22601
  19. Building Photo - 21 S Stewart St
    2 BEDS, 2 BATHS
    $2,200
    Total Monthly Price Total Monthly Price New
    Base Rent$2,200
    Required Monthly FeesNone
    Total Monthly Price$2,200

    21 S Stewart St Unit 4

    21 S Stewart St, Winchester, VA 22601
  20. 3 BEDS, 2 BATHS
    $2,225
    Total Monthly Price Total Monthly Price New
    Base Rent$2,225
    Required Monthly FeesNone
    Total Monthly Price$2,225

    314 E Piccadilly St

    314 E Piccadilly St, Winchester, VA 22601
  21. 3 BEDS, 2 BATHS
    $2,225
    Total Monthly Price Total Monthly Price New
    Base Rent$2,225
    Required Monthly FeesNone
    Total Monthly Price$2,225

    312 E Piccadilly St

    312 E Piccadilly St, Winchester, VA 22601
  22. Building Photo - 222 Walker St
    3 BEDS, 2.5 BATHS
    $2,295
    Total Monthly Price Total Monthly Price New
    Base Rent$2,295
    Required Monthly FeesNone
    Total Monthly Price$2,295

    222 Walker St

    222 Walker St, Winchester, VA 22601
  23. Building Photo - 629 Watson Ave
    3 BEDS, 1.5 BATHS
    $2,400
    Total Monthly Price Total Monthly Price New
    Base Rent$2,400
    Required Monthly FeesNone
    Total Monthly Price$2,400

    629 Watson Ave

    629 Watson Ave, Winchester, VA 22601
  24. Building Photo - 213 N Kent St
    3 BEDS, 3 BATHS
    $2,450
    Total Monthly Price Total Monthly Price New
    Base Rent$2,450
    Required Monthly FeesNone
    Total Monthly Price$2,450
         - 12 Month Lease

    213 N Kent St Unit 213

    213 N Kent St, Winchester, VA 22601
    Apply
  25. Building Photo - 1805 Harvest Dr
    4 BEDS, 3.5 BATHS
    $2,500
    Total Monthly Price Total Monthly Price New
    Base Rent$2,500
    Required Monthly FeesNone
    Total Monthly Price$2,500
         - 12 Month Lease

    1805 Harvest Dr

    1805 Harvest Dr, Winchester, VA 22601
    Apply
  26. Building Photo - 210 E Boscawen St
    2 BEDS, 2 BATHS
    $2,500
    Total Monthly Price Total Monthly Price New
    Base Rent$2,500
    Required Monthly FeesNone
    Total Monthly Price$2,500

    210 E Boscawen St Unit 200

    210 E Boscawen St, Winchester, VA 22601
  27. Building Photo - 209 N Washington St
    4 BEDS, 3 BATHS
    $3,500
    Total Monthly Price Total Monthly Price New
    Base Rent$3,500
    Required Monthly FeesNone
    Total Monthly Price$3,500

    209 N Washington St

    209 N Washington St, Winchester, VA 22601
  28. 3 BEDS, 2.5 BATHS
    $3,700
    Total Monthly Price Total Monthly Price New
    Base Rent$3,700
    Required Monthly FeesNone
    Total Monthly Price$3,700

    703 S Loudoun St

    703 S Loudoun St, Winchester, VA 22601
Showing 42 of 70 results, Page 2 of 2

Can't find what you are looking for?

Clear All Filters

Winchester at a Glance

Average Rent

N/A
(All bedrooms and property types)
0

School Rating

out of 10 Rating
Learn more about
Schools in Winchester

Top Budget-Friendly Neighborhoods in Winchester

(For 1 bedroom apartments)

Education

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.