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Newest Homes for Rent in Chester, VT

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  • 735 Main St, Chester, VT 05143
    735 Main St, Chester, VT 05143
    735 Main St, Chester, VT 05143
    /11

    $3,300 Per Month

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft
    • House for Rent

    735 Main St, Chester, VT 05143

    SUMMER SEASON RENTAL!! ...Lovely antique home within walking distance of Chester Village. Fully furnished, clean & comfortable. A great place to relax and enjoy all of what VT has to offer. All utilities except rubbish removal are paid by the owner. $3,300.00 per month plus deposit. Available for the 2026 summer season, June 1 - September 30. References and credit check required.

    Team BVA Rentals Barrett and Valley Associates Inc.

    735 Main St, Chester, VT 05143
  • 659 Davidson Hill Rd Unit 2, Chester, VT 05143
    659 Davidson Hill Rd Unit 2, Chester, VT 05143
    659 Davidson Hill Rd Unit 2, Chester, VT 05143
    /16

    $1,400 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    659 Davidson Hill Rd Unit 2, Chester, VT 05143

    659 Davidson Hill Rd Unit 2, Chester, VT 05143
  • 32 S Main St Unit 7, Chester, VT 05143
    32 S Main St Unit 7, Chester, VT 05143
    32 S Main St Unit 7, Chester, VT 05143
    /8

    $1,400 Per Month

    • 2 Beds
    • 1 Bath
    • 750 Sq Ft
    • Apartment for Rent

    32 S Main St Unit 7, Chester, VT 05143

    Traditional two bedroom apartment on Main Street in Chester. Walking distance to amenities. Coin-op laundry on site.$1,400.00 per month with heat included. No pets.References and credit check required.

    Team BVA Rentals Barrett and Valley Associates Inc.

    32 S Main St Unit 7, Chester, VT 05143
  • 32 S Main St Unit 4, Chester, VT 05143
    32 S Main St Unit 4, Chester, VT 05143
    32 S Main St Unit 4, Chester, VT 05143
    /6

    $1,100 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Apartment for Rent

    32 S Main St Unit 4, Chester, VT 05143

    Traditional one bedroom apartment on Main Street in Chester. Walking distance to amenities. Coin-op laundry on site.$1,100.00 per month with heat included. No pets.References and credit check required.

    Team BVA Rentals Barrett and Valley Associates Inc.

    32 S Main St Unit 4, Chester, VT 05143
  • 96 S Main St, Chester, VT 05143
    96 S Main St, Chester, VT 05143
    96 S Main St, Chester, VT 05143
    /17

    $3,200

    Total Monthly Price

    • 4 Beds
    • 2.5 Baths
    • 2,220 Sq Ft
    • House for Rent

    96 S Main St, Chester, VT 05143

    Spacious 4-Bedroom Home with Large Backyard in the Heart of Chester, VT.Welcome to 96 S Main St — a charming and well-appointed 4-bedroom, 2.5-bath home offering 2,215 square feet of comfortable living space in the very heart of Chester village.Inside, you’ll find a bright and generous living room and dining room perfect for relaxing or entertaining, a functional kitchen with all

    96 S Main St, Chester, VT 05143
Vermont Windsor County Chester

Newest Homes for Rent in Chester, VT

Frequently Asked Questions

How much does it cost to rent a home in Chester, VT?
The median rent for a home in Chester, VT is $1,400 per month, though prices vary by neighborhood, size, and property type. As of May 2026, condos tend to be the most affordable option while single-family homes are currently more expensive.
How much do you need to make to afford rent in Chester, VT?
To comfortably afford the median rent in Chester, VT, a household needs to earn roughly $56,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $1,400 per month in Chester, VT, renters typically need to show $4,200 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Chester, VT?
In Chester, VT, the price-to-rent ratio is 23.5, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Chester, VT are best for renting a home?
The best neighborhood for renting in Chester, VT depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include West Side and East Side, each with its own character and price range.

Rental Home Trends in Chester, VT

There are currently 5 homes available for rent in Chester, VT. The median rent is $1,400 per month, with single-family homes renting at $3,200 and condos at $1,300.

Rental Home Trends

Number of Homes for Rent
5
Median Rent
$1,400
Median Single Family Home Rent
$3,200
Median Condo Rent
$1,300
How to Rent a Home

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