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Windham County, VT Rentals

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  • 3550 Coolidge Hwy Unit Short Term Rental, Guilford, VT 05301
    3550 Coolidge Hwy Unit Short Term Rental, Guilford, VT 05301
    3550 Coolidge Hwy Unit Short Term Rental, Guilford, VT 05301
    /15

    $1,350 per month

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

    3550 Coolidge Hwy Unit Short Term Rental, Guilford, VT 05301

    Property Id: 2293016Welcome to your new cozy 1 bedroom, 1 bathroom unit located at 3550 Coolidge Highway in Guilford, VT. This multi-family property features hardwood floors, a washer and dryer in-unit, and a balcony/deck for relaxing outdoors. Rent includes garbage, internet, sewage, and water. Small dogs and cats are welcome. Don't miss out on this charming rental for $1350/month

    3550 Coolidge Hwy Unit Short Term Rental, Guilford, VT 05301
  • 91 Central St Unit 2, Brattleboro, VT 05301
    91 Central St Unit 2, Brattleboro, VT 05301
    91 Central St Unit 2, Brattleboro, VT 05301
    /6

    $1,800 per month

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    91 Central St Unit 2, Brattleboro, VT 05301

    Property Id: 2252475This furnished one-bedroom apartment in Downtown Brattleboro is available starting at $1800 month (all utilities included). This is an outstanding opportunity for medical professionals as it's located within a 10 minute-walk from Brattleboro Memorial Hospital and the Brattleboro Retreat. However, this could work for anyone interested in a mid-term rental between a

    91 Central St Unit 2, Brattleboro, VT 05301
  • 722 Vermont 30, Townshend, VT 05353
    722 Vermont 30, Townshend, VT 05353
    722 Vermont 30, Townshend, VT 05353
    /12

    $1,700 per month

    • 1 Bed
    • 1 Bath
    • 524 Sq Ft
    • House for Rent

    722 Vermont 30, Townshend, VT 05353

    Single Family home located in Townshend, newly renovated with fresh paint and flooring. All rooms have natural light and plenty of windows to enjoy the nature right outside the window. This home has a large private yard, just minutes from shopping.

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    722 Vermont 30, Townshend, VT 05353
  • 197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301
    197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301
    197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301
    /38

    $2,000 per month

    • 3 Beds
    • 1 Bath
    • 2,200 Sq Ft
    • Condo for Rent

    197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301

    Available December 1Spacious and sun-filled 3-bedroom apartment with an additional office, offering room to live, work, and relax. Enjoy a full dining room, large kitchen, comfortable living room, and your own private porch—perfect for morning coffee or unwinding at the end of the day.This home features new windows, clean carpeting, and excellent natural light from every direction. You’ll

    197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301
  • 131 Green St, Brattleboro, VT 05301
    131 Green St, Brattleboro, VT 05301
    131 Green St, Brattleboro, VT 05301
    /12

    $1,400 per month

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

    131 Green St, Brattleboro, VT 05301

    Welcome to your future home in the charming district of Brattleboro, VT! This delightful property offers a perfect blend of comfort and convenience, situated just minutes away from great dining options and the Brattleboro Memorial Hospital.This 1st floor, one bedroom, 3 room residence features ample living space with central heating.Please note that rent does include heat, hot

    131 Green St, Brattleboro, VT 05301
  • 4 Elliot St Unit 11, Brattleboro, VT 05301
    4 Elliot St Unit 11, Brattleboro, VT 05301
    4 Elliot St Unit 11, Brattleboro, VT 05301
    /9

    $1,700 per month

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

    4 Elliot St Unit 11, Brattleboro, VT 05301

    In town, one bedroom apartment, with bright sunlit rooms. The apartment has a combined kitchen and living room, with a separate bedroom. Coin operated laundry is on site, trash removal, and a secure building. Pet friendly building, Photos are virtually staged and apartment is not furnished.

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 11, Brattleboro, VT 05301
  • 1889 Vermont 30 Unit 1, Townshend, VT 05353
    1889 Vermont 30 Unit 1, Townshend, VT 05353
    1889 Vermont 30 Unit 1, Townshend, VT 05353
    /6

    $1,700 per month

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

    1889 Vermont 30 Unit 1, Townshend, VT 05353

    First Floor 2 bedroom apartment with natural light, close to town and is available now. Off street parking and a yard make the location ideal. Apartment is not furnished

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    1889 Vermont 30 Unit 1, Townshend, VT 05353
  • 167 Howard Rd Unit 2, Wardsboro, VT 05355
    167 Howard Rd Unit 2, Wardsboro, VT 05355
    167 Howard Rd Unit 2, Wardsboro, VT 05355
    /12

    $2,000 per month

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

    167 Howard Rd Unit 2, Wardsboro, VT 05355

    Property Id: 2203648One bedroom one bathroom apartment completely remodeled, open concept located on a dead end road in Wardsboro Vermont. Furnished/Unfurnished/ Partially furnished upon tenants request. Close to Mount Snow, Stratton & Bromley Mountains. Use of one bay in garage. All kitchen appliances are new stainless steel in addition landlord provides blender, coffeemaker,

    167 Howard Rd Unit 2, Wardsboro, VT 05355
  • 4 Elliot St Unit 3, Brattleboro, VT 05301
    4 Elliot St Unit 3, Brattleboro, VT 05301
    4 Elliot St Unit 3, Brattleboro, VT 05301
    /8

    $1,700 per month

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

    4 Elliot St Unit 3, Brattleboro, VT 05301

    The National, featuring this 1 Bedroom apartment with bright sunlit rooms, amazing hardwood floors and views of downtown. Coin operated Laundry is on site and off-street parking is available in the parking garage. The building is pet friendly

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 3, Brattleboro, VT 05301
  • 21 Vermont 121 Unit 1,2,4,5,6, Grafton, VT 05146
    21 Vermont 121 Unit 1,2,4,5,6, Grafton, VT 05146
    21 Vermont 121 Unit 1,2,4,5,6, Grafton, VT 05146
    /26

    $500 per month

    • 2 Baths
    • 352 Sq Ft
    • House for Rent

    21 Vermont 121 Unit 1,2,4,5,6, Grafton, VT 05146

    OFFICE SPACE AVAILABLE. The Windham Walkups now available for rent. Second floor office spaces now available above the Grafton Garage in Grafton Village VT. 5 separate office spaces are available and vary in rent based on size from $425-$650/month. Rent includes heat, electric and plowing. Shared parking area located just behind building. Two shared bathrooms and kitchenette space. Work remotely

    Jessica Landers Barrett and Valley Associates Inc.

    21 Vermont 121 Unit 1,2,4,5,6, Grafton, VT 05146
  • 67 Vermont Route 100, Jamaica, VT 05155
    67 Vermont Route 100, Jamaica, VT 05155
    67 Vermont Route 100, Jamaica, VT 05155
    /29

    $18,000 per month

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

    67 Vermont Route 100, Jamaica, VT 05155

    Discover the charm of this delightful rental nestled along a quintessential river in Vermont! With its prime location on a major road, you're just 7 miles away from the slopes of the Stratton Mountain ski resort, making it the perfect getaway for winter sports enthusiasts. This spacious home boasts multiple living areas, ensuring everyone has their own space to relax and unwind. With four

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    67 Vermont Route 100, Jamaica, VT 05155
  • 1070 Hells Peak Rd, Londonderry, VT 05148
    1070 Hells Peak Rd, Londonderry, VT 05148
    1070 Hells Peak Rd, Londonderry, VT 05148
    /23

    $5,000 per month

    • 3 Beds
    • 1.5 Baths
    • 2,092 Sq Ft
    • House for Rent

    1070 Hells Peak Rd, Londonderry, VT 05148

    Charming Antique Home on 60 Acres – Hell’s Peak Road, Londonderry, Vermont Set on 60 rolling acres in the quaint hamlet of Londonderry, this beautiful antique home offers the perfect Vermont retreat. With availability for the upcoming 2025–26 ski season, it’s an ideal opportunity for those seeking both seasonal enjoyment and year-round serenity. Located near three premier ski areas with a direct

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    1070 Hells Peak Rd, Londonderry, VT 05148
  • 1138 River Rd, Jamaica, VT 05343
    1138 River Rd, Jamaica, VT 05343
    1138 River Rd, Jamaica, VT 05343
    /33

    $6,000 per month

    • 5 Beds
    • 3 Baths
    • 2,912 Sq Ft
    • House for Rent

    1138 River Rd, Jamaica, VT 05343

    WINTER MONTHLY RENTAL - $6,000/Month Plus prepaid utilities ($750/month) | Total due in Full Before Occupancy. Spend the winter in the mountains with this spacious and fully updated 5-bedroom, 3-bath home with a cozy loft in scenic Jamaica, VT. Nestled in a quiet wooded setting, this inviting retreat comfortably accommodates up to 12 guests. After a day on the slopes, relax by the fireplace with

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    1138 River Rd, Jamaica, VT 05343
  • 4669 Vermont Route 100, Londonderry, VT 05148
    4669 Vermont Route 100, Londonderry, VT 05148
    4669 Vermont Route 100, Londonderry, VT 05148
    /32

    $35,000 per month

    • 7 Beds
    • 4.5 Baths
    • 5,343 Sq Ft
    • House for Rent

    4669 Vermont Route 100, Londonderry, VT 05148

    GET THE BEST OF THE BEST. Just the 3 prime skiing months..JAN- MARCH. NOW AT A VERY REDUCED RATE!! Very Special rental opportunity... for 2 very lucky families. Sleeps 12+ easily. An amazing house, property, outbuildings, barns, land, total privacy.. to spend a totally fun enchanting winter together in Vermont heaven. This beautifully restored Vermont classic farmhouse has room for many, 2

    Wilkie Bushby TPW Real Estate

    4669 Vermont Route 100, Londonderry, VT 05148
  • 1303 Goodaleville Rd, South Londonderry, VT 05155
    1303 Goodaleville Rd, South Londonderry, VT 05155
    1303 Goodaleville Rd, South Londonderry, VT 05155
    /24

    $40,000 per month

    • 5 Beds
    • 5 Baths
    • 3,000 Sq Ft
    • House for Rent

    1303 Goodaleville Rd, South Londonderry, VT 05155

    Stunning expansive farmhouse ready for your winter enjoyment. Just ten minutes from Stratton's access road entrance . Located on a beautiful country road. 5 attractive bedrooms , 3 full baths, 2 half baths. Yoga room. Sauna. Wood burning fireplace. Garage. This decorator appointed home is the perfect winter vacation respite for you and your family and friends. Utilities , Owners's

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    1303 Goodaleville Rd, South Londonderry, VT 05155
  • 923 Landgrove Rd, Londonderry, VT 05148
    923 Landgrove Rd, Londonderry, VT 05148
    923 Landgrove Rd, Londonderry, VT 05148
    /23

    $4,000 per month

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

    923 Landgrove Rd, Londonderry, VT 05148

    This three-bedroom, three-bathroom cape is located in the exclusive rural town of Landgrove and it is absolutely darling. Situated on a huge parcel of land equipped with space for snowshoeing, cross-country skiing, and a pond. Enjoy your "tucked away" Norman Rockwell style winter/ski home this season and reap the benefits and ease of being just a short drive from Stratton, Bromely,

    Peggy O'neill Cummings & Co

    923 Landgrove Rd, Londonderry, VT 05148
  • 3A Black Pine Unit ID1261564P, Dover, VT 05356
    3A Black Pine Unit ID1261564P, Dover, VT 05356
    3A Black Pine Unit ID1261564P, Dover, VT 05356
    /20

    $12,537 per month

    • 3 Beds
    • 3 Baths
    • 1,194 Sq Ft
    • Condo for Rent

    3A Black Pine Unit ID1261564P, Dover, VT 05356

    This gorgeous three-bedroom condo is situated directly across from Mount Snow, offering everything you need for the perfect getaway. Whether you're planning a ski trip in the winter, an action-packed summer vacation, or a relaxing fall leaf-peeping trip, this is a great spot to call your home away from home. Wake up in the morning and take in the beautiful views of Mount Snow from your windows;

    3A Black Pine Unit ID1261564P, Dover, VT 05356
  • 3550 Coolidge Hwy, Guilford, VT 05301
    3550 Coolidge Hwy, Guilford, VT 05301
    3550 Coolidge Hwy, Guilford, VT 05301
    /12

    $1,000 per month

    • 1 Bed
    • 1 Bath
    • 200 Sq Ft
    • House for Rent

    3550 Coolidge Hwy, Guilford, VT 05301

    Property Id: 1565026THIS IS A SHARED SPACE - ROOMMATE WANTEDSpacious 1-bedroom shared property located at 3550 Coolidge Highway in Guilford, VT. Built in 1979, this cozy unit comes with modern amenities including a refrigerator, washer, dryer, and more. Enjoy the convenience of off-street parking, on-site laundry, and a fireplace. Utilities included in the rent are electric,

    3550 Coolidge Hwy, Guilford, VT 05301
  • 4 Elliot St Unit 8, Brattleboro, VT 05301
    4 Elliot St Unit 8, Brattleboro, VT 05301
    4 Elliot St Unit 8, Brattleboro, VT 05301
    /13

    $2,200 per month

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

    4 Elliot St Unit 8, Brattleboro, VT 05301

    The National, featuring this 2 Bedroom apartment with bright sunlit rooms, amazing hardwood floors and views of downtown and the mountain. Coin operated Laundry is on site and off street parking is available in the parking garage. The building is pet friendly

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 8, Brattleboro, VT 05301
  • 4591 Vermont 30, Jamaica, VT 05343
    4591 Vermont 30, Jamaica, VT 05343
    4591 Vermont 30, Jamaica, VT 05343
    /14

    $2,500 per month

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft
    • House for Rent

    4591 Vermont 30, Jamaica, VT 05343

    ITS NOT TOO LATE.. SNOW IS JUST STARTING TO FLY..This is a delightful Winter retreat...After a long fun day of skiing come home to this warm and cozy, meticulously maintained 4 bedroom home that is in great shape. Just 8 minutes from Stratton access Rd.Upstairs there are 2.5 bedrooms , kitchen, and living room with wood burning fireplace. Downstairs is another full bedroom and a 2nd kitchen,

    Wilkie Bushby TPW Real Estate

    4591 Vermont 30, Jamaica, VT 05343
  • 111 Wiswall Hill Rd Unit Tiny home/mini cottage, Newfane, VT 05345
    111 Wiswall Hill Rd Unit Tiny home/mini cottage, Newfane, VT 05345
    111 Wiswall Hill Rd Unit Tiny home/mini cottage, Newfane, VT 05345
    /19

    $850 per month

    • Studio
    • 1 Bath
    • 200 Sq Ft
    • Condo for Rent

    111 Wiswall Hill Rd Unit Tiny home/mini cottage, Newfane, VT 05345

    Initial lease term will be months to months to ensure both sides are happy with the living situation as the cottage is in close proximity to our main home.utilities can be agreed on with a flat fee of aprox $150.-/monthdriveway will be snow cleared by the owner. walkway to the unit and stairs are the responsibility of the tenant. parking is available.

    111 Wiswall Hill Rd Unit Tiny home/mini cottage, Newfane, VT 05345
  • 194 Main St, Grafton, VT 05146
    194 Main St, Grafton, VT 05146
    194 Main St, Grafton, VT 05146
    /32

    $4,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,080 Sq Ft
    • House for Rent

    194 Main St, Grafton, VT 05146

    VACATION RENTAL. In the center of Grafton Village find the refined Phebe Frost house. Beautifully maintained and thoughtfully decorated, spend some special time in Vermont! Lovely features include wood floors, double sided fireplace in living and dining, comfortable family room/den and stocked pantry. Delightful master suite on main floor and two additional bedrooms bookend a full bath upstairs.

    Jessica Landers Barrett and Valley Associates Inc.

    194 Main St, Grafton, VT 05146
Vermont Windham County

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