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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 6 Apr 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 housing is rented out compared to 42% of homes are owned, according to the most recent Census Bureau estimates. 7% of Winchester's apartments are found in large buildings of 50 units or more, 60% are located in smaller apartment complexes with less than 50 units, and 33% are single-family rentals.

Search for apartments in Winchester, VA under $2,000

There’s more than one way to spend $2,000 on rent in Winchester, VA, so the first step is to start thinking about what you really want from your new home. Be mindful of what makes you tick. Look for 2 bedroom apartments for rent for less than $2,000 if you want to share your living space and don’t mind being further away from the city center. Search for 3 bedroom apartments if you’re moving in with family or planning to share part of your life and living expenses with more friends. If city bustle is what you live for, you might want to search for a studio or 1 bedroom apartment closer to the city center.

The perfect $2,000 rental near you

Don’t dismiss the idea of a studio just because it sounds small and featureless: studios come in many shapes and sizes, and it only takes a few strikes of creativity to go from drab to lively. If an all-in-one-room apartment spells total lack of privacy for you, have a look at the 1 bedroom apartments for rent in Winchester, VA. Customize your search by using more RentCafe filters. Decide what amenities you can’t live without and focus your search on the apartments that offer them. Are you bringing in a pet? Narrow your options to pet-friendly apartments for rent. Want more windows so that natural light floods your home? Hardwood floors or plush carpet in the living area? There are 12 apartments for rent below $2,000 in Winchester, VA for every taste. Decide what you need, stay focused, and you’re bound to find your perfect apartment in no time.

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