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

176 Rentals
.
  2. Building Photo - 318 S Braddock St
    1 BED, 1 BATH
    $1,000
    Total Monthly Price Total Monthly Price New
    Base Rent$1,000
    Required Monthly FeesNone
    Total Monthly Price$1,000

    318 S Braddock St

    318 S Braddock St, Winchester, VA 22601
  3. 1 BED, 1 BATH
    $1,000
    Total Monthly Price Total Monthly Price New
    Base Rent$1,000
    Required Monthly FeesNone
    Total Monthly Price$1,000

    510 N Kent St Unit 1

    510 N Kent St, Winchester, VA 22601
  4. Building Photo - ZeroPak Apartments
    1 BED
    $1,013+
    2 BEDS
    $1,218+
    Plus Fees - 12 Month Lease

    ZeroPak Apartments

    570 N Cameron St, Winchester, VA 22601
  5. Building Photo - 1704 Roberts St
    1 BED, 1 BATH
    $1,124
    Total Monthly Price Total Monthly Price New
    Base Rent$1,124
    Required Monthly FeesNone
    Total Monthly Price$1,124

    1704 Roberts St Unit 1

    1704 Roberts St, Winchester, VA 22601
  9. 2 BEDS, 1 BATH
    $1,200
    Total Monthly Price Total Monthly Price New
    Base Rent$1,200
    Required Monthly FeesNone
    Total Monthly Price$1,200

    24 W Cecil St

    24 W Cecil St, Winchester, VA 22601
  10. 1 BED, 1 BATH
    $1,200
    Total Monthly Price Total Monthly Price New
    Base Rent$1,200
    Required Monthly FeesNone
    Total Monthly Price$1,200

    553 N Loudoun St Unit 1

    553 N Loudoun St, Winchester, VA 22601
  11. 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

    208 W Boscawen St Unit 12

    208 W Boscawen St, Winchester, VA 22601
  12. 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

    378 National Ave

    378 National Ave, Winchester, VA 22601
  13. 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

    235 Kern St

    235 Kern St, Winchester, VA 22601
  14. Building Photo - 25 W Boscawen St
    2 BEDS, 1.5 BATHS
    $1,350
    Total Monthly Price Total Monthly Price New
    Base Rent$1,350
    Required Monthly FeesNone
    Total Monthly Price$1,350
         - 12 Month Lease

    25 W Boscawen St Unit 3

    25 W Boscawen St, Winchester, VA 22601
    Apply
  15. Building Photo - 113 W Boscawen St
    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

    113 W Boscawen St Unit #3

    113 W Boscawen St, Winchester, VA 22601
  16. 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

    103 W Germain St

    103 W Germain St, Winchester, VA 22601
  17. Building Photo - 301 S Braddock St
    1 BED, 1 BATH
    $1,400
    Total Monthly Price Total Monthly Price New
    Base Rent$1,400
    Required Monthly FeesNone
    Total Monthly Price$1,400
         - 12 Month Lease

    301 S Braddock St Unit 3

    301 S Braddock St, Winchester, VA 22601
    Apply
  18. Building Photo - 434 Fairmont Ave
    2 BEDS, 1 BATH
    $1,400
    Total Monthly Price Total Monthly Price New
    Base Rent$1,400
    Required Monthly FeesNone
    Total Monthly Price$1,400

    434 Fairmont Ave

    434 Fairmont Ave, Winchester, VA 22601
  19. Building Photo - 447 N Loudoun St
    2 BEDS, 1 BATH
    $1,400
    Total Monthly Price Total Monthly Price New
    Base Rent$1,400
    Required Monthly FeesNone
    Total Monthly Price$1,400

    447 N Loudoun St

    447 N Loudoun St, Winchester, VA 22601
  20. 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

    224 1/2 Kern Street Unit 224 1/2

    224 1/2 Kern St, Winchester, VA 22601
  21. 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

    208 W Boscawen St Unit 5

    208 W Boscawen St, Winchester, VA 22601
  22. 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

    224 Kern St

    224 Kern St, Winchester, VA 22601
  23. Building Photo - 1660 S Braddock St
    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

    1660 S Braddock St

    1660 S Braddock St, Winchester, VA 22601
  24. Building Photo - 127-A Peyton Street
    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
  25. Pemberton Village Exterior - PEMBERTON
    2 BEDS
    $1,525+
    3 BEDS
    $1,800+
    Plus Fees

    PEMBERTON

    660 Pemberton Dr, Winchester, VA 22601
  26. Building Photo - End Unit Townhouse!!
    3 BEDS, 1.5 BATHS
    $1,525
    Total Monthly Price Total Monthly Price New
    Base Rent$1,525
    Required Monthly FeesNone
    Total Monthly Price$1,525

    End Unit Townhouse!!

    221 Kimberly Way, Winchester, VA 22601
  27. Building Photo - 443 Millwood Ave
    2 BEDS, 2 BATHS
    $1,550
    Total Monthly Price Total Monthly Price New
    Base Rent$1,550
    Required Monthly FeesNone
    Total Monthly Price$1,550

    443 Millwood Ave Unit 2

    443 Millwood Ave, Winchester, VA 22601
  28. Building Photo - 210 N Kent St
    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
  29. 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
  30. STUDIO
    $1,600+
    1 BED
    $1,800+
    2 BEDS
    $2,600+
    Plus Fees - 1 Month Lease

    114 N Loudoun St

    114 N Loudoun St, Winchester, VA 22601
    Apply
  31. 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

    1819 Henry Ave

    1819 Henry Ave, Winchester, VA 22601
  32. 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

    1815 Henry Ave

    1815 Henry Ave, Winchester, VA 22601
  35. Building Photo - Fort Collier Terrace
    2 BEDS
    $1,722+
    3 BEDS
    $1,822+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,695 - $1,795
    Required Monthly Fees$27
    Total Monthly Price$1,722 - $1,822

    Fort Collier Terrace

    900-1024 N Braddock St, Winchester, VA 22601
    (540) 409-4434
  36. Building Photo - 211 Sharp St
    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

    211 Sharp St

    211 Sharp St, Winchester, VA 22601
  37. Building Photo - The Local
    Rent Special
    Rent Special
    |
    1 BED
    $1,700+
    2 BEDS
    $1,900+
    3 BEDS
    $2,100+
    4 BEDS
    $3,900+
    Plus Fees

    The Local

    230 Spring St, Winchester, VA 22601
    (434) 443-6043
  39. Building Photo - 228 Opequon Ave
    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
  40. 1 BED, 1 BATH
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    25 E Boscawen St Unit 301

    25 E Boscawen St, Winchester, VA 22601
  42. Building Photo - 137 Fox Dr
    2 BEDS, 1 BATH
    $1,810
    Total Monthly Price Total Monthly Price New
    Base Rent$1,810
    Required Monthly FeesNone
    Total Monthly Price$1,810

    137 Fox Dr

    137 Fox Dr, Winchester, VA 22601
Showing 42 of 64 results, Page 1 of 2

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
0

Some Transit

out of 100 TransitScore® Rating
Learn more about
Transportation in Winchester
49

Somewhat Bikeable

out of 100 BikeScore® Rating
Learn more about
Transportation in Winchester

Downtown Winchester Neighborhood in Winchester, VA

When looking for cheap apartments in Downtown Winchester, Apartment Finder is your deal-hunting partner. Whether you’re looking for a studio, a one-bedroom, or a two-bedroom apartment, you want the best place at the right price. We have a great selection of budget-friendly apartments for rent, and we’ll show you which apartments offer the best value when compared to other apartments in Downtown Winchester.

Finding a rental that fits your budget without compromising on quality can seem like a challenge, but Apartment Finder makes it easy to discover cheap apartments with all the features you want. To find an apartment you can afford, try looking in less popular neighborhoods outside of the city center. Timing is everything when searching for rentals that are affordable, so look at different times of the day, different days of the week and (if you can wait) certain months like December through March. When you find an apartment with a great price, don’t hesitate! Cheap apartments tend to go very quickly.

Affordability doens't have to equal sacrifice. While it’s important to be flexible, you might not have to give up as much as you think. You can find a cheap apartment for rent, complete with must-have amenities such as paid utilities and an in-unit washer and dryer. Click on any of these properties to see photos and floor plans, read reviews, check out the rent calculator, and learn more about the neighborhood with information on nearby parks, shopping malls, and transit stops. With 64 cheap apartments available in Downtown Winchester, Apartment Finder is the place to find your next rental.

Top Budget-Friendly Neighborhoods in Winchester

(For 1 bedroom apartments)

Getting Around Winchester

Transportation

79

Very Walkable

out of 100 WalkScore® Rating
You might be able to get out and walk when living in this area. Some errands can be accomplished on foot, but for others you need a car.
49

Somewhat Bikeable

out of 100 BikeScore® Rating
You might be able to find places to ride your bike in this area, but you'll most likely want your car for most errands.
0

Minimal Transit

out of 100 TransitScore® Rating
You'll likely want a car when living in this area since it has few transit options.
Scores provided by Walk Scoreⓘ

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.