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Explore Similar Homes Within 10 Miles of Chester, MA

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    $1,800 - $1,995 per month plus fees

    Brookview Townhomes

    2 Beds

    140 Union St, Westfield, MA 01085

    Brookview Townhomes offers peaceful Westfield, MA townhomes for rent.Shaded by trees and tucked away from hectic city life, our community is only a short drive to many area conveniences. Our community is located just minutes away from shopping and dining, as well as multiple local colleges and universities. Our newly remodeled two bedroom apartments for rent offer bright spacious kitchens

    140 Union St, Westfield, MA 01085
  • /10

    $2,000 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,472 Sq Ft
    • House for Rent

    8 Greylock St, Westfield, MA 01085

    Don’t miss this exceptional rental opportunity. This beautifully updated 2-3 bedroom home combines modern comfort with classic charm. Spacious living room featuring a cozy fireplace. The kitchen has been completely renovated with updated appliances, while the refreshed bathroom and new flooring throughout create a move-in-ready space. Second-floor loft offers exciting possibilities: transform it

    Domingo Medina Coldwell Banker Realty - Lexington

    8 Greylock St, Westfield, MA 01085
  • /30

    $1,500 - $1,850 per month plus fees

    Longhill Gardens

    1 - 2 Beds

    134 College Hwy, Southampton, MA 01073

    Newly renovated apartmentsWalking distance to Paisano's Pizzeria, DUNKIN', ESB Bank, Cumberland Farms, And More! Do not miss out on this great offer!Completely remodeled unit that features large living room/kitchen and 2 large bedrooms.New Kitchen with Stainless Steel Appliances.Coin operated Laundry is on site with a workout facility on site.Close to

    134 College Hwy, Southampton, MA 01073
  • /7

    $1,695 total monthly price

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

    13 Hampden St Unit 2, Westfield, MA 01085

    Downtown Westfield beautifully renovated 2-bedroom apartment in the heart of downtown Westfield, just steps from restaurants, shops, and nightlife. Features include two full bedrooms, spacious living area, brand-new kitchen with stainless steel appliances, dishwasher, and granite countertops, updated bathroom with tub/shower, free in-unit laundry, hardwood floors, and modern lighting. Heat and

    Rosanna Lopez Witman Properties, Inc.

    13 Hampden St Unit 2, Westfield, MA 01085
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    $2,004 - $2,114 total monthly price

    The Willows

    1 - 2 Beds

    19 Lockhouse Rd, Westfield, MA 01085

    Discover a blend of timeless New England charm and urban access at The Willows Apartments in Westfield, Massachusetts. Nestled off the beaten path, our thoughtfully designed one- and two-bedroom apartments are crafted for those in search of a tranquil escape without compromising on convenient access to all that Westfield has to offer, and beyond. Enjoy our pet-friendly accommodations, embrace the

    19 Lockhouse Rd, Westfield, MA 01085
  • /9

    $2,050 total monthly price

    • 2 Beds
    • 1 Bath
    • Apartment for Rent

    20 Perkins St Unit 1, Westfield, MA 01085

    20 Perkins St offers spacious and comfortable place. This 2-bedroom, 1-bath apartment is perfectly located. This apartment has a 3rd room that can function as a 3rd bedroom. Enjoy a prime location close to downtown Westfield, shops, restaurants, parks, and public transportation. A perfect opportunity for tenants seeking convenience, charm, and a place to feel at home.

    Adaliz Diaz Naples Realty Group

    20 Perkins St Unit 1, Westfield, MA 01085
  • /35

    $1,928 - $2,593 per month plus fees

    Southwood Acres

    1 - 2 Beds

    342 Southwick Rd, Westfield, MA 01085

    Welcome to Southwood Acres Apartments in Westfield, MA, where extraordinary living meets the heart of Pioneer Valley. Nestled in the beautiful rural landscapes of Western Massachusetts, our community offers a unique blend of resort-style amenities and a down-to-earth, country-inspired lifestyle. Here, you'll discover a haven of tranquility and convenience, with a host of exceptional features

    342 Southwick Rd, Westfield, MA 01085
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    $2,780 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,823 Sq Ft
    • House for Rent

    52 Valley Rd, Southampton, MA 01073

    Recently remodeled single-family home with newer bathrooms and new kitchen with all appliances, marble countertops, and new cabinets. First floor bathroom has walk-in shower and full laundry with new washer & gas dryer. Mix of new and old wood floors with tile in bathrooms. Features a large enclosed heated side porch and rear deck. Situated in a convenient location in Southampton with large yard

    Tim Murphy River Valley Realty Service

    52 Valley Rd, Southampton, MA 01073
  • /6

    $1,495 - $1,695 per month plus fees

    Evergreen Manor Apartments

    2 Beds

    919 Southampton Rd, Westfield, MA 01085

    The Evergreen Manor Apartments is located only 2 miles from the Mass Pike (Rt 90) entrance on Route 202. Located in a quiet country setting just minutes from grocery stores and other local retailers. We offer spacious and well maintained two bedroom/ 1 bath apartments. All apartments feature updated kitchens and bathrooms, LED lighting, modern energy efficient appliances, quartz or granite

    919 Southampton Rd, Westfield, MA 01085
  • /26

    $7,500 total monthly price

    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    320 Lakeshore Dr, Sandisfield, MA 01253

    Wow! You must see to fully appreciate how special this home truly is. The construction quality is not only exceptional, but it is also new this year. The open floor plan log home features impactful vaulted ceilings, a spacious eat-in kitchen and pantry, a bright dining area, and an eye-catching Great Room with an effective wood burning stove. Four attractive bedrooms, 3 1/2 bathrooms, an office

    George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    320 Lakeshore Dr, Sandisfield, MA 01253
  • /9

    $625 per month plus fees

    • 1 Bed
    • 1 Bath
    • House for Rent

    936 Russell Rd, Westfield, MA 01085

    Property Id: 957523AVAILABLE MARCH 1, 2026 Seeking male roommate who is clean and respectful. Private Furnished Room in house shared with 3 other male roommates.Rent includes all utilities including fiber optic WIFI. Shared Bath and Kitchen in Duplex House on Russell Road. PLEASE NOTE: Shared with 3 other male, mature, quiet and respectful roommatesBedroom

    936 Russell Rd, Westfield, MA 01085
  • /19

    $2,500 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,276 Sq Ft
    • House for Rent

    240 Russellville Rd, Westfield, MA 01085

    For Rent recently renovated 3 bedroom single family home in Westfield. 1st floor: living/dining room combo w fireplace; kitchen w island, refrigerator, range & dishwasher; bedroom with closet. 2nd floor: Full bath & 2 more bedrooms with closets. Laundry with washer & dryer in basement. First month rent, last month rent & security deposit are required $2,500 each (total $7,500). Tenant is

    Ivan Karamian Berkshire Hathaway HomeServices Realty Professionals

    240 Russellville Rd, Westfield, MA 01085
  • /6

    $1,875 total monthly price

    • 3 Beds
    • 1 Bath
    • Condo for Rent

    18 Bates St Unit Second Floor Rear, Westfield, MA 01085

    Property Id: 1734861Welcome Home! This cozy updated 2nd-floor unit with 3 spacious bedrooms is available for immediate occupancy! Inside the unit, plenty of natural light with fresh paint and new vinyl flooring make the space feel bright and clean. In the large eat-in kitchen, you will find lots of storage with newer wood cabinets, countertops, and appliances, including a dishwasher. For

    18 Bates St Unit Second Floor Rear, Westfield, MA 01085
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    $2,950 total monthly price

    • 4 Beds
    • 1.5 Baths
    • 1,536 Sq Ft
    • House for Rent

    960 Westhampton Rd, Florence, MA 01062

    Welcome to your dream rental in desirable Northampton! This well-maintained 4BR, 1.5BA home sits on a scenic 0.39-acre corner lot surrounded by seasonal strawberry and pumpkin patches. Enjoy the gazebo with lights and sound, a heated above-ground pool (tenant to maintain pool), raised garden beds, and a private entrance to a nature trail. Solar panels help reduce utility costs, and the landscaped

    Arien Monti Keller Williams Realty

    960 Westhampton Rd, Florence, MA 01062
  • /7

    $1,995 total monthly price

    • 3 Beds
    • 1.5 Baths
    • 1,450 Sq Ft
    • House for Rent

    11 Meadow St, Westfield, MA 01085

    Property Id: 2268636Beautifully renovated single family home conveniently located in downtown Westfield. Fully applianced kitchen with granite countertops opens up to a dining room for the perfect combination of style, comfort and convenience. Large living room and half bath complete the main level. Second floor includes three bedrooms and a full bathroom. Gas Heat. Gas and Electric not

    11 Meadow St, Westfield, MA 01085
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    $1,800 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Apartment for Rent

    34 Kellogg St Unit 2, Westfield, MA 01085

    Welcome to this spacious 3-bedroom apartment located on the second floor of a well-kept home on Kellogg Street in Westfield, MA. This bright and inviting unit offers a comfortable layout with three generously sized bedrooms, a full bathroom, and a large living area perfect for relaxing or entertaining. The kitchen is well-equipped with ample cabinet space and room for dining. Washer and dryer

    Sheila Perez Naples Realty Group

    34 Kellogg St Unit 2, Westfield, MA 01085
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    $1,900 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    36 Fowler St Unit 1st Floor, Westfield, MA 01085

    Fully remodeled on the exterior (new roof & siding) with a freshly painted and hardwood refinished interior ON THE FIRST FLOOR! Prime location in Westfield NEXT TO A PARK brand new refrigerator. New washer. 2 bedrooms and a bathroom with a kitchen and living room. Gas heating with dedicated washer & dryer in the basement. Right next to a park!! Walking distance to downtown, away from the

    36 Fowler St Unit 1st Floor, Westfield, MA 01085
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    $1,795 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,245 Sq Ft
    • Apartment for Rent

    15 Casimir St Unit 3, Westfield, MA 01085

    David Vilkhovoy VP Management

    15 Casimir St Unit 3, Westfield, MA 01085
  • /8

    $2,800 total monthly price

    • 5 Beds
    • 2 Baths
    • 2,808 Sq Ft
    • House for Rent

    75 Franklin St, Westfield, MA 01085

    Westfield University. off campus house, close to town, close to school, right on the bus line. Well cared for home, hardwood floors, large rooms, sleeps up to 6. Avail Aug 15th, 2026.Large yard, plenty of parking.

    75 Franklin St, Westfield, MA 01085
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    $2,400 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    28 Ridgeway St Unit A, Westfield, MA 01085

    Heat, hot water, electricity is included in this newly renovated throughout .Amazing kitchen, bath, living room & two bedroom apartment in quiet, suburban type neighborhood.new flooring in kitchen & bathroom, hardwood in the rest.Large yard, and for your outdoor fun, and the garage is negotiable.

    28 Ridgeway St Unit A, Westfield, MA 01085
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    $1,750 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Condo for Rent

    51 Crown St Unit 2, Westfield, MA 01085

    51 Crown St Unit 2, Westfield, MA 01085
  • /5

    $862 total monthly price

    • 3 Beds
    • 1 Bath
    • 3,500 Sq Ft
    • Townhouse for Rent

    5 Clark St, Westfield, MA 01085

    Downtown Westfield Apartment – 3 Bed / 1 BathMy friend Miller and I are looking for either a solo renter or a group to share our 3-bedroom, 1-bath apartment in downtown Westfield. We don’t have a preference—just looking for the right fit.We’re both in our early 20s, laid-back, and keep things clean and comfortable with a moderate living style. The apartment is spacious, with a

    5 Clark St, Westfield, MA 01085
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    $1,950 total monthly price

    • 2 Beds
    • 1.5 Baths
    • 864 Sq Ft
    • Condo for Rent

    268 College Hwy Unit 268, Southampton, MA 01073

    Lovely 2-bedroom townhouse located in beautiful Southampton available now. This one feels like home with its many features. On the first floor you will find an eat in kitchen and a large living room with walk out access to the spacious deck/porch. Upstairs are 2 bedrooms, a full bath and a linen closet. The bright and sunny basement includes a washer & dryer, a half bath and walk out access to

    268 College Hwy Unit 268, Southampton, MA 01073
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    $2,250 total monthly price

    • 2 Beds
    • 1 Bath
    • 941 Sq Ft
    • House for Rent

    71 Pequot Rd, Southampton, MA 01073

    Enjoy peaceful waterfront living in Southampton. Lakefront house set on private 5-acre compound surrounded by conservation land with hiking trails on Hampton Ponds. Close to Easthampton, Northampton, Springfield and the Berkshires with exceptional dining, shopping and entertainment. Large 2-bedroom with upgrades throughout. New appliances, new floors and interior painting. Gas heat. Well water.

    71 Pequot Rd, Southampton, MA 01073

Why Live in Chester

Chester, Massachusetts, is a secluded hillside community located approximately 30 miles west of Springfield. Known for its privacy and tranquility, Chester appeals to residents seeking a quiet lifestyle, including musicians who appreciate the solitude for creative pursuits. Homes in Chester are surrounded by dense forests that showcase vibrant fall colors, and the area offers four-season recreational activities such as hiking and cross-country skiing. While major grocery shopping requires a drive to Westfield, local entertainment is readily available with the Chester Theatre Company producing acclaimed summer shows. Architectural styles in Chester range from Colonials and Cape Cods to contemporary designs, with many homes featuring decks or porches for enjoying the peaceful surroundings. The community is not particularly walkable or bikeable due to its spread-out nature. Chester boasts a thriving arts scene, with the Chester Theatre Company and the Chester Railway Station & Museum being notable attractions. Outdoor enthusiasts can explore Chester-Blandford State Forest, which offers hiking, snowmobiling, mountain biking, and more. Chester Town Park and Hampden Street Park provide additional recreational options. The Gateway Regional School District serves the area, though the schools have average ratings. Dining and shopping options within Chester are limited, but nearby Westfield offers more variety. Chester is connected to the rest of Hampden County via Route 20, which leads to Springfield and connects to Interstate 90. Bradley International Airport is 40 miles away, and Baystate Noble Hospital is a 30-minute drive from Chester.

Frequently Asked Questions

What are the most popular neighborhoods in Chester, MA for renters?
The most popular neighborhoods in Chester, MA for renters are Florence, Ashfield, Willimansett, Chicopee Center and Fairview.
What are the most popular zip codes in Chester, MA for renters?
The most popular zip codes in Chester, MA for renters include 01062, 01085, 01238, 01060 and 01040.
How to Rent a Home