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Explore Similar Homes Within 10 Miles of Chester, MA

  • /32

    Starting at $1,895 Plus Fees

    • 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

    Brookview Townhomes

    (413) 798-8652

    140 Union St, Westfield, MA 01085
  • /37

    Starting at $1,500 Plus Fees

    • 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

    Longhill Gardens

    (413) 287-8604

    134 College Hwy, Southampton, MA 01073
  • /20

    Starting at $2,137

    Total Monthly Price

    • 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

    The Willows

    (413) 287-8496

    19 Lockhouse Rd, Westfield, MA 01085
  • /20

    Starting at $2,043 Plus Fees

    • 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

    Southwood Acres

    (413) 666-1066

    342 Southwick Rd, Westfield, MA 01085
  • /6

    Starting at $1,495 Plus Fees

    • 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

    Evergreen Manor Apartments

    (413) 266-5314

    919 Southampton Rd, Westfield, MA 01085
  • /33

    $3,200 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,100 Sq Ft
    • Condo for Rent

    181 Park Ave Unit A, Dalton, MA 01226

    Spacious and bright remodeled unit offering four bedrooms and 2.5 bathrooms. First floor features and expansive living room and and kitchen with new granite countertops. Along with a formal dining room, half bathroom, laundry room, and bedroom. Second floor included a primary bedroom with en-suite and two additional bedrooms and another full bathroom. All rooms have new flooring, fresh paint, and

    Cory Evangelisto NOCHER REALTY

    181 Park Ave Unit A, Dalton, MA 01226
  • /29

    $1,575

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    7 Day Ave Unit 1R, Westfield, MA 01085

    Freshly updated 1st floor apartment in a sought after location within walking distance to the best of downtown Westfield's coffee shops, lunch spots & shopping. A minute to Stanly Park, Westfield State University & the bike path! The space features an enclosed porch, sizeable living room w/ wood floors, bedroom, full bathroom & eat-in kitchen. Laundry, private off street parking, and basement

    7 Day Ave Unit 1R, Westfield, MA 01085
  • /54

    $8,400 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,374 Sq Ft
    • Property for Rent

    66 Access Rd, Becket, MA 01223

    Opportunities are right outside your door: Cool off in the community swimming pond after playing a few games of tennis on the two clay courts or after taking a hike within the community. Come back to the tastefully designed main home perfect for friends with an open plan kitchen/living space with 3 bedrooms. The stunning attached conditioned barn with grand vaulted ceiling and rustic wood is the

    Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

    66 Access Rd, Becket, MA 01223
  • /10

    $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
  • /3

    $1,690 Per Month

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

    14,16,20 W Shore Dr Unit 1,2,4, Goshen, MA 01032

    This is the premier summer vacation lake in the valley. Swim, kayak(5), paddle board(1), trampoline raft, canoe(1), or sail on this this beautiful 100 acre private lake that is adjacent to the 1500 acre DAR with it's wonderful hiking and biking trails! Great fishing as well! All three cottages have their unique features and have high speed internet and are in a park like setting. There is an on

    Robert Raymond Hampshire Realty Company

    14,16,20 W Shore Dr Unit 1,2,4, Goshen, MA 01032
  • /21

    $2,800

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    131 N Elm St, Westfield, MA 01085

    ENTIRE HOUSE!!!! Fully renovated 2-story 3BR HOME with a private FENCED IN yard, BASEMENT & GARAGE! Efficient brand new central gas heating! Everything is brand new with only 2 previous tenants. White kitchen, granite counter tops, brand new appliances, designer bathroom and overall unique theme throughout. Basement with washer & dryer hookups & plenty of storage. Master bedroom on the first

    131 N Elm St, Westfield, MA 01085
  • /14

    $1,800 Per Month

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

    28 King St Unit 2, Westfield, MA 01085

    REMODELED apartment in downtown Westfield available now! Tenant pays utilities. Landlord includes water, landscaping, snow removal and trash removal. Coin-op laundry located on site on the first level. Fenced in back yard.

    Mark Rodgers American Made Real Estate Company

    28 King St Unit 2, Westfield, MA 01085
  • /17

    $1,800

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Condo for Rent

    18 King St Unit 1st fl unit, Westfield, MA 01085

    18 King St Unit 1st fl unit, Westfield, MA 01085
  • /15

    $3,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,557 Sq Ft
    • House for Rent

    33 S Main Rd, Otis, MA 01253

    AVAILABLE SEPTEMBER 1, 2026 T0 6/30/2027. Nicely renovated and beautifully furnished Colonial rental located in the heart of Otis. The updated eat-in kitchen is enhanced by attractive wood floors that exist throughout the home. The bathrooms, the propane furnace, and the windows have also been updated. The town has provided high speed broadband service throughout the community so if you need to

    George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    33 S Main Rd, Otis, MA 01253
  • /13

    $1,500

    Total Monthly Price

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

    25 Chester Rd, Becket, MA 01223

    2-Bedroom House in Becket – Quiet, Private, and Fully FurnishedEnjoy peaceful living in this standalone, fully renovated 2-bedroom, 1-bath house located in beautiful Becket, MA. No shared walls — just privacy and quiet.Inside the Home:Primary bedroom: Spacious, includes a queen bed, a large closet, and a desk.Second bedroom/office: Perfect for a twin bedroom or a

    25 Chester Rd, Becket, MA 01223
  • /26

    $7,500 Per Month

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

    320 Lakeshore Dr, Sandisfield, MA 01253

    WINTER RENTAL FROM 10/1/2026 TO 3/15/2027. 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

    George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    320 Lakeshore Dr, Sandisfield, MA 01253
  • /16

    $1,750

    Total Monthly Price

    • Studio
    • 1 Bath
    • 1,000 Sq Ft
    • Townhouse for Rent

    93 George St Unit Studio, Westfield, MA 01085

    Freshly painted 1st floor! Beautiful home in the heart of Westfield - walking distance to downtown and minutes from MASS PIKE. Recently painted! Hardwood floors throughout, dining room has pocket doors that can turn into 3rd bedroom! In addition to a spacious living room. Beautiful kitchen.

    93 George St Unit Studio, Westfield, MA 01085
  • /11

    $1,785 Per Month

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • Apartment for Rent

    38 Thomas St Unit 307, Westfield, MA 01085

    Welcome Home! Conveniently located in the heart of Westfield, this beautifully renovated 2 bedroom corner apartment awaits its new residents. Amenities include on site laundry, covered parking garage, on site gym, bike path access and bicycle storage as well. Just a stone's throw to many local shops and restaurants for added convenience. Units feature newly renovated kitchens and baths as well as

    Rich Tariff William Raveis R.E. & Home Services

    38 Thomas St Unit 307, Westfield, MA 01085
  • /19

    $1,500

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    29 Chester Rd, Becket, MA 01223

    Two-bedroom, one-bath house with porch and private deck in Becket.Located in the middle of Berkshire!Beautiful house with two big bedrooms, a living room, a dining room combo, and a huge porch.The house is furnished. Equipped kitchen with a big fridge, Oven with stove top, coffee machine, and microwave.Each bedroom features a double bed.Huge close porch with big tables with an

    29 Chester Rd, Becket, MA 01223
  • /8

    $1,775 Per Month

    • 2 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • Apartment for Rent

    95 N Elm St Unit 2, Westfield, MA 01085

    In town living in a Victorian. Step back into time with HIgh Ceilings, large rooms, eat-in kitchen, dining room, living room, study. Washer and dryer hookup available. Two parking spots off street.

    Ruth Aborjaily Berkshire Hathaway HomeServices Realty Professionals

    95 N Elm St Unit 2, Westfield, MA 01085
  • /10

    $2,000

    Total Monthly Price

    • 1 Bed
    • 1.5 Baths
    • 864 Sq Ft
    • House for Rent

    108 Lindsay Hill Rd, Worthington, MA 01098

    This is a NEW complete building renovation on 25 acres of forest in a beautiful and quiet hill town between Pittsfield and Northampton. This lovely property is on a gravel road with neighbors down the road, but not in sight. The whole second floor is a very large bedroom. Everything in the house is new: gas range, dishwasher, refrigerator, washer and dryer and mini splits. Farmhouse sink, heated

    108 Lindsay Hill Rd, Worthington, MA 01098
  • /13

    $2,195 Per Month

    • 4 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
  • /14

    $2,025

    Total Monthly Price

    • 3 Beds
    • 1.5 Baths
    • 1,300 Sq Ft
    • Condo for Rent

    87 Highland Ave Unit 1st floor, Westfield, MA 01085

    Spacious 3BR Near Stanley Park — Renovated Kitchen, Garage, 1st FloorBring the family home to this beautifully updated 3-bedroom apartment in one of Westfield’s quietest, most desirable neighborhoods. Just a short walk (about a mile) to Stanley Park — 300 acres of gardens, playgrounds, duck ponds, and walking trails right at your doorstep.At 1,300 sq ft, there’s room for everyone to

    87 Highland Ave Unit 1st floor, Westfield, MA 01085
  • /19

    $1,800 Per Month

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

    15 S Main St Unit A, Williamsburg, MA 01096

    Bright and airy 2-bedroom first-floor apartment with a private entrance! This inviting home features a beautiful blend of refinished hardwood floors and stylish LVP flooring throughout. The spacious living room is filled with natural light and includes a charming nook—perfect for a reading corner. The large kitchen offers plenty of room for cooking and gathering, while the open feel of the living

    Miranda Gonthier Maverick Realty

    15 S Main St Unit A, Williamsburg, MA 01096
  • /6

    $1,600

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    13 Hampden St Unit 13 Hampden Street, Westfield, MA 01085

    13 Hampden St Unit 13 Hampden Street, Westfield, MA 01085
  • /13

    $1,995

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • Condo for Rent

    15 Casimir St Unit 2, Westfield, MA 01085

    Spacious 3BR apartment in the heart of Westfield, MA! Enjoy an updated kitchen, hardwood floors, and a well-maintained bathroom. Perfect for comfortable living and entertaining, with unbeatable access to local amenities. Modern, stylish, and move-in ready!Amenities: Hardwood Floors, spacious, Updated Kitchen, great location

    15 Casimir St Unit 2, Westfield, MA 01085
  • /37

    $3,275

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,797 Sq Ft
    • Beautiful 4 Bed / 2 Bath, Single Family Home. Close to Downtown Northampton!

    1195 Burts Pit Rd, Northampton, MA 01062

    Welcome to your new home! This 4-bedroom, 2 bath single family home sits just outside of downtown Northampton! You feel welcomed as soon as you enter. The first floor has an open concept living room, dining room, and kitchen. Adorned with stainless steel appliances, you can whip up all of your favorites to enjoy on the breakfast island or in your dining room. The vaulted ceilings, skylight, and

    1195 Burts Pit Rd, Northampton, MA 01062

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, Chicopee Center, Chicopee Falls, Liberty Heights and Willimansett.
What are the most popular zip codes in Chester, MA for renters?
The most popular zip codes in Chester, MA for renters include 01238, 01085, 01060, 01240 and 01040.
How to Rent a Home