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Apartments for Rent in Winchester, VA under $2000

27 Rentals Available
Apartments for Rent in Winchester, VA under $2000. 27 Rentals Available
  • a kitchen with white appliances and wooden cabinets
    Today

    996 N. Braddock St., Winchester, VA 22601
    1 BED $999+
    2 BEDS $1,320
    3 BEDS Ask for Pricing
  • a living room with a long wooden dining table and a couch
    Today

    1981 Randolph Place, Winchester, VA 22601
    1 BED $1,720+
    2 BEDS $1,970+
  • a kitchen with white cabinets and a sink and a refrigerator
    Today

    164 N. Indian Alley, Winchester, VA 22601
    1 BED $1,300
  • a living room with two green chairs and a couch
    Today

    2260 Wilson Blvd, Winchester, VA 22601
    2 BEDS $1,375
  • a kitchen with white appliances and wooden cabinets
    Today

    996 N. Braddock St., Winchester, VA 22601
    1 BED $1,025
    2 BEDS Ask for Pricing
    3 BEDS Ask for Pricing
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  • a living room with a white couch and two blue chairs
    Today

    1864 Old Jube Square, Winchester, VA 22601
    1 BED $1,915
    2 BEDS $1,950+
  • an empty kitchen with black appliances and wooden floors
    Today

    15 S. Cameron Street, Winchester, VA 22601
    1 BED $1,300
  • an empty living room with a white door and window
    Today

    15 S. Cameron Street, Winchester, VA 22601
    1 BED $1,400
  • a row of town houses on a street
    Today

    603 Chatham Square, Winchester, VA 22601
    3 BEDS $1,650
  • our apartments are located on the corner of a city street
    Today

    150 Panay Way, Winchester, VA 22602
    1 BED $1,300
  • LOT 82 3 Beds Apartment for Rent
    Today

    LOT 82, Winchester, VA 22602
    3 BEDS $1,000
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  • a townhouse icon vector isolated on white background illustration
    Today

    LOT 80, Winchester, VA 22602
    2 BEDS $2,000
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Getting around in Winchester, VA

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Walk Score®: 1

Frequently asked questions

When were prices and availability in Winchester, VA last updated?

Prices and availability in Winchester, VA were last updated on 19 Feb 2026.

What are the best apartments in Winchester, VA?

The best apartments in Winchester, VA are: Fay Street Apartments, Stuart Hill, 164 N. Indian Alley Apt #4, Blue Ridge Apartments and Fort Collier Terrace.

What type of rental buildings are in Winchester, VA?

In Winchester, 58% of the residents are renting compared to 42% owning a home, according to data from the U.S. Census Bureau. Large-scale apartment buildings with more than 50 units represent 7% of Winchester's rentals, 60% are small-scale complexes with under 50 units, and 33% are single-family rentals.

Renting apartments in Winchester, VA under $2,000

Searching for apartments for rent in Winchester, VA under $2,000 is not an easy task, but luckily you have come to the right place. Whether you are a student on a budget, a young professional on the move, or simply a frugal person, RentCafe can help you find what you are looking for. Just make sure you know what you consider non-negotiable and what you can compromise on. Your new home is just a few clicks away. In Winchester, VA, where the average rent is $1,551 per month, there are 27 units available for less than $2,000. Click on any of these units to see pictures, floor plans, amenities and more. After you have picked your favorite, you can contact the property to check availability. Considering that you are trying to spend as little as possible, looking at 1 bedroom apartments and studio apartments might be a good idea.

We’ll help you find the cheapest rental near you

Finding a nice cheap apartment is by no means impossible. You just have to be patient. Your “apartments near me under $2,000” search can bear fruit sooner than you think if you look carefully and check our site often. You never know when discount deals and special offers might pop up. Keep in mind that you are not the only one looking for an affordable apartment in Winchester, VA. Choose “Save Search” to receive the latest apartments available directly to your inbox. This way, you will be able to stay one step ahead of the competition. With the cheapest apartments in Winchester, VA going for $999 per month, there are great deals waiting to be discovered. Feeling lucky? Expand your search to 2 bedroom apartments and 3 bedroom apartments as well for more space.

Finding a home nearby is easier than you think. Check out our Apartments Near Me page and take your pick!