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Explore Similar Houses Within 25 Miles of Windsor, MA

  • /32

    $22,000 per month

    • 6 Beds
    • 5.5 Baths
    • 5,400 Sq Ft
    • House for Rent

    61 Red Fox Ln, Craryville, NY 12521

    SEASONAL RENTAL - book your 2025 visits now! Set amongst the bucolic Berkshire foothills surrounding Lake Copake, this newly built and beautifully appointed modern farmhouse style vacation home offers exceptional indoor and outdoor living with a covered porch, pergola, grill kitchen, and hot tub overlooking the links of the Copake Country Club and the lake beyond. Full of amenities and

    Agent Photo

    Veronica Newton

    Compass Greater NY, LLC

    (518) 684-7165

    61 Red Fox Ln, Craryville, NY 12521
  • /17

    $12,500 per month

    • 3 Beds
    • 2 Baths
    • 1,861 Sq Ft
    • House for Rent

    5 Beachwood Dr, Stockbridge, MA 01262

    Delightful, classic Berkshires summer cottage in the Beachwood enclave. Shares in gorgeous community beach at south end of the Stockbridge Bowl (Lake Mahkeenac.) Enjoy swimming, kayaking, etc. Minutes to Tanglewood and all the cultural delights of the Berkshires. 3BR including primary suite with bath. 1 Queen BR, 1 Br with double bunk beds. Fantastic large screened porch with dining. LR with

    Agent Photo

    Selina Lamb

    Birch Properties

    (413) 610-3637

    5 Beachwood Dr, Stockbridge, MA 01262
  • /50

    $20,000 per month

    • 5 Beds
    • 7 Baths
    • 4,645 Sq Ft
    • House for Rent

    42 Golf Course Rd, Craryville, NY 12521

    Escape to Casa do Lago: A Luxurious Seasonal Retreat on Copake LakeSEASONAL VACATION RENTAL! Unwind in peace at this exquisite 5-bedroom, 6.5-bath lakefront home, nestled next to a picturesque 18-hole golf course and charming farm-to-table restaurant. Located in the heart of the Hudson Valley, Copake Lake offers the perfect backdrop for your seasonal getaway, with Casa do Lago providing the ideal

    Agent Photo

    Veronica Newton

    Compass Greater NY, LLC

    (518) 662-7619

    42 Golf Course Rd, Craryville, NY 12521
  • /20

    $975 per month

    • 1 Bed
    • 1.5 Baths
    • House for Rent

    240 Greenaway Dr, Springfield, MA 01109

    Property Id: 2037213*FOR STUDENTS ONLY* This newly renovated home is perfect for students! Being close to all Springfield Colleges, you're only a very short walk to Western New England University, a short 3.5 mile drive to Springfield College, & American International College & less than 5 miles to Springfield Technical Community College! Saving you money & hassle, it comes furnished down

    240 Greenaway Dr, Springfield, MA 01109
  • /41

    $1,000 per month

    • 1 Bed
    • 1 Bath
    • 1,370 Sq Ft
    • House for Rent

    1118 Boston Rd, Springfield, MA 01119

    WIFI INCLUDED!!!! Now available for rent a room at 1118 Boston Rd, Springfield, MA 01119 — a clean and spacious bedroom, located in a convenient and well-connected area. This unit offers generous natural light, hardwood flooring, a large living room, and a functional eat-in kitchen with ample cabinet space. Enjoy easy access to shopping, dining, public transportation, and major roadways.

    Lucy Cordero Tarpinian Keller Williams Realty

    1118 Boston Rd, Springfield, MA 01119
  • /20

    $1,000 per month

    • 1 Bed
    • 1.5 Baths
    • House for Rent

    240 Greenaway Dr, Springfield, MA 01109

    Property Id: 2037196*FOR STUDENTS ONLY* This newly renovated home is perfect for students! Being close to all Springfield Colleges, you're only a very short walk to Western New England University, a short 3.5 mile drive to Springfield College, & American International College & less than 5 miles to Springfield Technical Community College! Saving you money & hassle, it comes furnished down

    240 Greenaway Dr, Springfield, MA 01109
  • /19

    $5,500 per month

    • 6 Beds
    • 3.5 Baths
    • 4,772 Sq Ft
    • House for Rent

    60 Red Gate Ln, Amherst, MA 01002

    Perfect rental opportunity and convenient to all the amenities Amherst has to offer! This lovely home, built in 2006, offers 6 bedrooms, 3.5 bathrooms, 2 large home offices, an attached 2 car garage, and a private outdoor seating area overlooking beautiful plantings and a lovely wooded area that leads to the local elementary, middle, and high school. Additional features include hardwood floors

    Kate Duggan Bostonia Properties

    60 Red Gate Ln, Amherst, MA 01002
  • /20

    $950 per month

    • 1 Bed
    • 1.5 Baths
    • House for Rent

    240 Greenaway Dr, Springfield, MA 01109

    Property Id: 2037094*FOR STUDENTS ONLY*This newly renovated home is perfect for students! Being close to all Springfield Colleges, you're only a very short walk to Western New England University, a short 3.5 mile drive to Springfield College, & American International College & less than 5 miles to Springfield Technical Community College!Saving you money & hassle, it comes

    240 Greenaway Dr, Springfield, MA 01109
  • /11

    $2,390 per month

    • 2 Beds
    • 1.5 Baths
    • 1,800 Sq Ft
    • House for Rent

    15 Casimir St Unit rear, Westfield, MA 01085

    Welcome to your new home in the heart of Westfield, MA! This newly renovated apartment offers three spacious bedrooms and a full bathroom, perfect for those who value comfort and style.

    David Vilkhovoy VP Management

    15 Casimir St Unit rear, Westfield, MA 01085
  • /20

    $1,050 per month

    • 1 Bed
    • 1.5 Baths
    • House for Rent

    240 Greenaway Dr, Springfield, MA 01109

    Property Id: 2037215*FOR STUDENTS ONLY* This newly renovated home is perfect for students! Being close to all Springfield Colleges, you're only a very short walk to Western New England University, a short 3.5 mile drive to Springfield College, & American International College & less than 5 miles to Springfield Technical Community College! Saving you money & hassle, it comes furnished down

    240 Greenaway Dr, Springfield, MA 01109
  • /22

    $4,250 per month

    • 3 Beds
    • 2 Baths
    • 2,170 Sq Ft
    • House for Rent

    61 Schoolhouse Rd, New Lebanon, NY 12125

    Welcome to this beautifully updated 3 BR/2 bath classic ranch home with new timber frame front porch, situated on 5 gorgeous acres! Brand new kitchen with soapstone counters, lovely warm new wide-plank floors, new doors which let in great light, wood stove in the living area-- in an agricultural setting, located between Chatham, the Berkshires and Albany.Sign up for Queechy Lake rights and

    Janet Kain The Kinderhook Group, Inc.

    61 Schoolhouse Rd, New Lebanon, NY 12125
  • /2

    $800 per month

    • 1 Bed
    • 1 Bath
    • House for Rent

    30 Grattan St, Springfield, MA 01119

    Property Id: 2035135House is shared by 4 travel medical college students. Has 4 individual locked bedrooms with 2 full bathrooms. One openingFor college students and travel medical that need a great place to study. Quiet street and safe neighborhood in sixteen acres.Includes taxes, Wi-Fi, trash pickup, water, large yard, lawn care, heat, electricity, water, great parking (on and

    30 Grattan St, Springfield, MA 01119
  • /10

    $7,500 per month

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

    5 Fairview Ave, Chatham, NY 12037

    A Queen Anne Daydream . 1874 Victorian for Rent in the Chatham Village.Step into a world where time lingers a little longer and beauty is in every detail. Available for lease is a lovingly furnished 1874 Queen Anne Victoriana€''an elegant 4-bedroom, 2.5-bath home where history, charm, and comfort entwine effortlessly.Wrapped in a gracious porch made for lemonade afternoons and

    Brittany Craig Houlihan Lawrence Inc.

    5 Fairview Ave, Chatham, NY 12037
  • /19

    $850 per month

    • 1 Bed
    • 2 Baths
    • House for Rent

    1093 Dwight St, Holyoke, MA 01040

    Property Id: 1739603Private furnished bedroom in one of Holyoke's Grand Victorian homes. Shared kitchen and bathroom. Full-size bed, off-street parking, laundry on site, single occupancy only, absolutely no smoking on the property, no pets. Credit and background check required with application. You must have a good credit score, no prior evictions, income must be at least 3 times

    1093 Dwight St, Holyoke, MA 01040
  • /15

    $1,995 per month

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

    549 Russell Rd Unit 12D, Westfield, MA 01085

    Beautifully Updated 2-Bedroom Condo at Fairway Condos in Westfield with FREE heat, hot water, gas and water! Welcome to this crisp, clean, and freshly painted unit offering the perfect blend of comfort, convenience, and value. Featuring a spacious open floor plan, this condo boasts an updated kitchen with new appliances, brand-new laminate flooring throughout, and a fully renovated bathroom. The

    Vickie Allen Coldwell Banker Realty

    549 Russell Rd Unit 12D, Westfield, MA 01085
  • /2

    $1,100 per month

    • 1 Bed
    • 1 Bath
    • House for Rent

    165 Benmont Ave, Bennington, VT 05201

    Property Id: 1488761I bed 1 bath small house.The tenants pay their own utilities:heat electric etc…

    165 Benmont Ave, Bennington, VT 05201
  • /12

    $3,000 per month

    • 3 Beds
    • 1.5 Baths
    • 1,215 Sq Ft
    • House for Rent

    68 Benton St, Springfield, MA 01109

    Welcome to 68 Benton Street — a beautifully renovated single-family home tucked away on a quiet street in Springfield. This charming 3-bedroom, 1.5-bath rental offers a perfect blend of modern upgrades and classic New England character.Step inside to gleaming hardwood floors that have been newly sanded and poly-coated, fresh interior paint throughout, and a brand-new kitchen featuring updated

    Anthony Ardolino Berkshire Hathaway HomeServices Realty Professionals

    68 Benton St, Springfield, MA 01109
  • /48

    $2,900 per month

    • 1 - 3 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • House for Rent

    1579 Pleasant St, South Lee, MA 01260

    Greek revival farmhouse built in 1815 on national historic registry...2min drive to Main St in Stockbridge, 5min drive to Main Street in Lee, 8min drive to Main Street in Lenox, 15min drive to GB. Easy commute to Fairview or BMC. Separate entrances for each unit. Separate Kitchens for each unit. Separate Laundry Machines (Washer/Dryer) for each unit in-unit.

    1579 Pleasant St, South Lee, MA 01260
  • /18

    $3,200 per month

    • 3 Beds
    • 1.5 Baths
    • 1,428 Sq Ft
    • House for Rent

    765 Harlemville Rd, Hillsdale, NY 12529

    Tucked up against hill and overlooking farmland, you'll find this peaceful retreat, a Harlemville hideaway. This home is available September 1st for a 1 year lease. The perfect spot if you are looking to get away to the country but still want to be within reach of amenities or you want or need to be close to Hawthorne Valley which is only a 2 min drive or 10 min walk away. The house, a rustic

    Jennifer Sesma Beach & Bartolo Realtors

    765 Harlemville Rd, Hillsdale, NY 12529
  • /48

    $3,600 per month

    • 1 - 3 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • House for Rent

    1579 Pleasant St, South Lee, MA 01260

    Greek revival farmhouse built in 1815 on national historic registry...2min drive to Main St in Stockbridge, 5min drive to Main Street in Lee, 8min drive to Main Street in Lenox, 15min drive to GB. Easy commute to Fairview or BMC. Separate entrances for each unit. Separate Kitchens for each unit. Separate Laundry Machines (Washer/Dryer) for each unit in-unit.

    1579 Pleasant St, South Lee, MA 01260
  • /37

    $2,300 per month

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • House for Rent

    34 Colorado Ave Unit 1, Greenfield, MA 01301

    Set up as a two family with 2 kitchens, 2 bathrooms, 3 total bedrooms but possible 4th bed. Perfect for large families or extended family looking for an inlaw / separate living area. No utilities included. Brand new oil boiler and attic and basement recently insulated by mass save. Located on a private cul de sac with one other home and one mechanic shop / warehouse which is also available for

    Nick Daher Broad Sound Real Estate, LLC

    34 Colorado Ave Unit 1, Greenfield, MA 01301
  • /48

    $3,800 per month

    • 1 - 3 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • House for Rent

    1579 Pleasant St, South Lee, MA 01260

    Greek revival farmhouse built in 1815 on national historic registry...2min drive to Main St in Stockbridge, 5min drive to Main Street in Lee, 8min drive to Main Street in Lenox, 15min drive to GB. Easy commute to Fairview or BMC. Separate entrances for each unit. Separate Kitchens for each unit. Separate Laundry Machines (Washer/Dryer) for each unit in-unit.

    1579 Pleasant St, South Lee, MA 01260
  • /23

    $9,000 per month

    • 4 Beds
    • 3.5 Baths
    • 3,332 Sq Ft
    • House for Rent

    66 Fiddlehead Ln, Ghent, NY 12075

    If you would like an Upstate country get-a-way for the a entire season for the sake of privacy or for an entire year to write a novel or entertain guests around a pond with a canoe but need contemporary surroundings for convenience, then our Fiddlehead Lane listing, just south of the lovely little Spencertown NY hamlet, is perfect for you. The proximity and privacy of this compound is

    Parker Meyer Four Seasons Sotheby's Int.

    66 Fiddlehead Ln, Ghent, NY 12075
  • /12

    $825 per month

    • 6 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • House for Rent

    85 N Branch Pkwy, Springfield, MA 01119

    House for rent!! Perfect for undergrad and graduate college students. The house is close to WNE, AIC, and Springfield College.SAFE location. 6 bedrooms. Each room has door with lock.Stove, Refrigerator included.11 month lease. August 1st 2025 - June 30 2026. All utilities (water, gas, electric) are covered by owner. Cable and internet are

    85 N Branch Pkwy, Springfield, MA 01119
  • /8

    $2,700 per month

    • 2 Beds
    • 1 Bath
    • 1,024 Sq Ft
    • House for Rent

    103 Kirby St, Chicopee, MA 01020

    Welcome home to this cozy and well-maintained 2-bedroom, 1-bath single-family home located in a quiet neighborhood on the Springfield/Chicopee line. This inviting property offers comfort, convenience, and a beautiful backyard perfect for relaxing or entertaining. Inside, you'll find a spacious living area, kitchen with ample cabinet space, and two bedrooms with plenty of natural light. The full

    Rich Tariff William Raveis R.E. & Home Services

    103 Kirby St, Chicopee, MA 01020
  • /4

    $2,400 per month

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

    177 Laurel St, Lee, MA 01238

    Located in Lee, is this 2BR, 1 Bath, duplex home, with updated bathroom tile floor, hardwood and laminated flooring throughout, freshly painted. No smoking 1st and last references and credit check

    177 Laurel St, Lee, MA 01238
  • /18

    $8,500 per month

    • 3 Beds
    • 2 Baths
    • 1,858 Sq Ft
    • House for Rent

    1100 Harlemville Rd, Ghent, NY 12075

    If you want to amplify that seasonal feeling, driving the Upstate's country roads until you reach your Greek Revival farmhouse tucked away very privately from the road and adjacent to tall grass hay fields blowing in the breeze is probably high on your list. We are pleased to offer a 3 bedroom 2 full bathroom historic farm house for lease for the upcoming school year to help fulfill your Upstate

    Parker Meyer Four Seasons Sotheby's Int.

    1100 Harlemville Rd, Ghent, NY 12075
  • /16

    $3,600 per month

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

    165 Stockbridge Rd, Lee, MA 01238

    Modern 2bdrm guesthouse w/ private porch with sweeping views on historic property. Price does not include utilities, but we can offer an all-inclusive monthly rate. Primary bedroom and the living room have skylights (sun-filled daytime). Primary bdrm has door to porch. Bathroom has Rain-shower and tub. Top of line W/D. Kitchen used and loved by chefs. Farmhouse dining table + kitchen

    165 Stockbridge Rd, Lee, MA 01238
  • /28

    $7,000 per month

    • 3 Beds
    • 1.5 Baths
    • 2,216 Sq Ft
    • House for Rent

    33 High St, Chatham, NY 12037

    Seasonal Rental with a pool in the Village of Chatham now available for the month of September. One month minimum rental. Sitting up on a hill on a quiet street this 3 bed, 1.5 bath village home is fully furnished and sleeps 6. The first level features a living room, dining room, kitchen, mudroom, half bath and sunroom. Access the rear patio from either the mudroom or sunroom where you'll find a

    Jennifer Sesma Beach & Bartolo Realtors

    33 High St, Chatham, NY 12037
  • /21

    $2,700 per month

    • 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
  • /17

    $25,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,490 Sq Ft
    • House for Rent

    35 Bird Ln, Copake, NY 12516

    Beautiful, open and sunny rental walking distance to Copake Lake. Vaulted great room, gourmet kitchen, inviting bedrooms make for the perfect place to spend some time.

    Emma French Gabel Real Estate

    35 Bird Ln, Copake, NY 12516
  • /10

    $6,300 per month

    • 5 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • House for Rent

    23 N Maple St, Hadley, MA 01035

    Make this large updated conveniently located house your next home. This house includes all standard appliances in addition to 2 fridges, dishwasher, washer and dryer, Nest thermostats and smart oil gauge. All off-street parking including a 2 car finished garage with plenty of storage throughout the house. A large well lit basement, porch and large back yard for entertaining guests. Property has

    23 N Maple St, Hadley, MA 01035
  • /14

    $3,900 per month

    • 3 Beds
    • 2.5 Baths
    • 2,012 Sq Ft
    • House for Rent

    136 Macedonia Rd, Chatham, NY 12037

    Your own Country Retreat! Beautiful Secluded Post and Beam home w/ large spring fed pond on 8 acres. Located only 10 minutes from the Village of Chatham. Open concept w/ rustic cozy feel with 3BR and 2 1/2 BA, large country kitchen, 2 family rooms, glass enclosed sun-room, field stone wood burning fireplace, pellet stove, laundry room with washer and dryer, first floor bedroom w/BA. Views of pond

    Elizabeth Hendler Berkshire Hathaway HomeService

    136 Macedonia Rd, Chatham, NY 12037
  • /21

    $6,450 per month

    • 5 Beds
    • 3.5 Baths
    • 2,500 Sq Ft
    • House for Rent

    36 N Maple St, Hadley, MA 01035

    Make this large updated conveniently located house your next home. This house includes all standard appliances in addition to 2 fridges, dishwasher, washer and dryer, Nest thermostats and smart oil gauge. All off-street parking including a 2 car finished garage with plenty of storage throughout the house. A large well lit basement, porch and large back yard for entertaining guests. Property has

    36 N Maple St, Hadley, MA 01035
  • /45

    $7,700 per month

    • 9 Beds
    • 5 Baths
    • 12,000 Sq Ft
    • House for Rent

    147 Rock City Rd, Old Chatham, NY 12136

    Escape the city and discover Bellavista Country Estate—a luxurious 12,000 sq. ft. Georgian brick home on 60 private acres in the foothills of the Berkshires, between the Hudson Valley and Berkshires. Perfect for getaways, house-hunting stays, or events, it features 6-9 bedrooms, 5 baths, fireplaces, a stocked kitchen, and formal dining. Enjoy an in-ground pool, gym, home theater, trails, a pond,

    Joseph Briggs William Pitt Sotheby's

    147 Rock City Rd, Old Chatham, NY 12136
  • /17

    $2,200 per month

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

    130 Mazarin St, Springfield, MA 01151

    Updated ranch in great section of Indian Orchard . Fenced yard with patio . New kitchen and newer bathroom. Available for showing after September 1st . Please submit application before asking for showing . Thank you

    130 Mazarin St, Springfield, MA 01151
  • /51

    $24,000 per month

    • 9 Beds
    • 5 Baths
    • 12,000 Sq Ft
    • House for Rent

    147 Rock City Rd, Old Chatham, NY 12136

    Escape the hustle of city life and discover Bellavista Country Estate, a luxurious 12,000 sq. ft. Georgian brick home nestled on 60 private acres in the foothills of the Berkshires, perfectly situated between the Hudson River Valley and the Berkshires. Whether you're looking for a serene getaway, a temporary home while house-hunting, or an unforgettable event venue, Bellavista offers the space,

    Joseph Briggs William Pitt Sotheby's Int'l

    147 Rock City Rd, Old Chatham, NY 12136
  • /18

    $2,950 per month

    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft
    • House for Rent

    375 Hadley Rd, Sunderland, MA 01375

    Come check out this lovely 4-bedroom home set on scenic Rt. 47 in Sunderland. Beautiful hardwood floors throughout, leaded glass windows, craftsman style interior millwork, updated kitchen and bathrooms, wrap around covered porch, views of farm fields and walking access to the Connecticut River. Easy access to UMass and the other colleges, Amherst, Northampton, and Greenfield. Oil fired furnace,

    375 Hadley Rd, Sunderland, MA 01375
  • /41

    $3,200 per month

    • 2 Beds
    • 3 Baths
    • 1,600 Sq Ft
    • House for Rent

    113 Norwich Lake, Huntington, MA 01050

    Welcome to 113 Norwich Lake! This year round, lake front oasis is a hidden gem. Stunning, serene views of the lake and surrounding skylines are just one element that makes this home spectacular. Enjoy all of the outdoor activities such as swimming, fishing, boating and skating right in the convenience of your backyard. Included is a private concrete dock, perfect for a boat owner. The 2 story

    Robert Canon Canon Real Estate, Inc.

    113 Norwich Lake, Huntington, MA 01050
  • /15

    $2,400 per month

    • 4 Beds
    • 1.5 Baths
    • 2,000 Sq Ft
    • House for Rent

    81 Bridge Rd, Northampton, MA 01062

    Furnished House available Sept 1st (earliest date) - June 15th (latest date) The owner will considered a lease that is a minimum of 6 months or lease up to 10 months)  4 bedroom, 1.5 bath fully furnished CAPE home with CENTRAL AC! Large bedroom with a king size bed, a guest room with a queen size bed, and a smaller room with a full sized bed and another room with two twin beds and a queen.

    81 Bridge Rd, Northampton, MA 01062
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