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Holliston, MA Homes for Rent

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  • 49 Windsor Dr Unit 201, Holliston, MA 01746
    49 Windsor Dr Unit 201, Holliston, MA 01746
    49 Windsor Dr Unit 201, Holliston, MA 01746
    /21

    $1,975 Per Month

    • 2 Beds
    • 1 Bath
    • 880 Sq Ft
    • Condo for Rent

    49 Windsor Dr Unit 201, Holliston, MA 01746

    Recently renovated and move-in ready 2-bedroom, 1-bath with immediate occupancy available now! Features include fresh paint and NEW carpeting throughout. The updated kitchen features NEW granite countertops, white shaker cabinets and a built-in microwave, opening to a bright living room with wall AC and thermal-efficient windows for year-round comfort. Shared laundry is conveniently located just

    Erika Steele REMAX Executive Realty

    49 Windsor Dr Unit 201, Holliston, MA 01746
  • 215 Trailside Way Unit 215, Ashland, MA 01721
    215 Trailside Way Unit 215, Ashland, MA 01721
    215 Trailside Way Unit 215, Ashland, MA 01721
    /15

    $2,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft
    • Condo for Rent

    215 Trailside Way Unit 215, Ashland, MA 01721

    Avail. June 1st pending new floors and painting. Beautiful, large, sunny, 2 bed, 2 full bath, top floor unit with cathedral ceilings at gorgeous Spyglass Hill! Includes in-unit laundry, central air, and private 2- car garage with extra storage. Two south-facing picture windows and 3 sliding doors allow plenty of natural light and access to private covered deck facing natural wooded area.

    Ted Wood Berkshire Hathaway HomeServices Commonwealth Real Estate

    215 Trailside Way Unit 215, Ashland, MA 01721
Massachusetts Middlesex County Holliston

Homes for Rent in Holliston, MA

Why Live in Holliston

Holliston, MA, is a small Boston suburb located 23 miles southwest of Downtown Boston, known for its highly rated school system and diverse housing options. The town features classic New England architecture, including antique colonials, Cape Cods, ranch styles, and new constructions, often situated on spacious lots. Holliston Public Schools, including Fred Miller Elementary, Robert Adams Middle, and Holliston High School, are well-regarded, offering a variety of extracurricular activities and a Montessori program. The downtown area along Central and Washington Streets is home to popular local businesses like Casey’s Pub, Coffee Haven, and Holliston Superette, fostering a strong sense of community. Residents enjoy numerous things to do, such as events organized by the Holliston Newcomers & Neighbors Club, steam engine train rides with the Waushakum Live Steamers, and seasonal farmers markets at Blair Square. Outdoor enthusiasts can explore Lake Winthrop, the Upper Charles Rail Trail, and Brentwood Conservation Land. Holliston has a lower crime risk compared to the national average. For transportation, the closest commuter rail is 6 miles north in Ashland, and Boston Logan International Airport is about 32 miles away. The town's proximity to Interstate 495 and Interstate 90 provides convenient access to Boston and other areas.

Learn more about living in Holliston

Frequently Asked Questions

How much does it cost to rent a home in Holliston, MA?
The median rent for a home in Holliston, MA is $2,487 per month, though prices vary by neighborhood, size, and property type. As of May 2026, condos tend to be the most affordable option while townhouses and single-family homes are currently more expensive.
How much do you need to make to afford rent in Holliston, MA?
To comfortably afford the median rent in Holliston, MA, a household needs to earn roughly $99,480 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 $2,487 per month in Holliston, MA, renters typically need to show $7,461 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 Holliston, MA?
In Holliston, MA, the price-to-rent ratio is 24.3, 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 Holliston, MA are best for renting a home?
The best neighborhood for renting in Holliston, MA depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include Downtown Franklin, Nobscot and Saxonville, each with its own character and price range.

Rental Home Trends in Holliston, MA

There are currently 2 homes available for rent in Holliston, MA. The median rent is $2,487 per month, with single-family homes renting at $3,200, townhouses at $3,110 and condos at $1,975.

Rental Home Trends

Number of Homes for Rent
2
Median Rent
$2,487
Median Single Family Home Rent
$3,200
Median Townhouse Rent
$3,110
Median Condo Rent
$1,975
How to Rent a Home

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