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Windham County, VT Rentals

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  • /9

    $2,500 per month

    • 2 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Townhouse for Rent

    950 Western Ave, Brattleboro, VT 05301

    This spacious townhouse is in the back of an historic building situated just off the common in West Brattleboro. Enjoy a quiet living spot surrounded by beautiful stone walls and gardens. Two large bedrooms and two full baths, with an additional room for office or hobbies. Open concept living room / kitchen with vaulted ceiling. A wood paneled dining area done in pub (Stube) style.

    950 Western Ave, Brattleboro, VT 05301
  • /12

    $1,800 per month

    • 1 Bed
    • 1 Bath
    • 1,100 Sq Ft
    • Condo for Rent

    29 Green St, Bellows Falls, VT 05101

    SHORT TERM/LONG TERM Rental available! Enjoy the best of Vermont in this gorgeous, centrally located historic home. Large first floor apartment (approximately 1100 square feet) convenient to all local and regional amenities!Minutes from I-91, you'll enjoy ease of travel to all points in north, south and central Vermont - and just across the Connecticut River you'll discover the

    29 Green St, Bellows Falls, VT 05101
  • /12

    $1,800 per month

    • 1 Bed
    • 1 Bath
    • 1,100 Sq Ft
    • Condo for Rent

    29 Green St, Bellows Falls, VT 05101

    SHORT TERM/LONG TERM Rental available! Enjoy the best of Vermont in this gorgeous, centrally located historic home. Large first floor apartment (approximately 1100 square feet) convenient to all local and regional amenities!Minutes from I-91, you'll enjoy ease of travel to all points in north, south and central Vermont - and just across the Connecticut River you'll discover the

    29 Green St, Bellows Falls, VT 05101
  • /11

    $1,650 per month

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

    110 Estey St Unit 3, Brattleboro, VT 05301

    This quaint 3rd floor apartment on a quiet side street in town. The apartment is partially furnished, with one off street parking space. The rent includes heat and electric. This unit shares laundry facilities with the apartment downstairs. This apartment as unique as it comes with individual rooms for the shower, sink and toilet. There is also an additional loft space for storage. Its a must see

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    110 Estey St Unit 3, Brattleboro, VT 05301
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    $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
  • /12

    $2,500 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
  • /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
  • /12

    $1,700 per month

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Condo for Rent

    566 S Main St Unit 566 South Main Street, Brattleboro, VT 05301

    Naturally sunlight 3 bedroom apartment with off street parking (2spots) within walking distances to Main Street, grocery stores, hospital, gym, restaurant, high school, middle school, career center, elementary school, and Fort Dummer State Park hiking trails.

    566 S Main St Unit 566 South Main Street, Brattleboro, VT 05301
  • /26

    $500 per month

    • 2 Baths
    • 352 Sq Ft
    • House for Rent

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

    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 but would rather

    Jessica Landers Barrett and Valley Associates Inc.

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

    $1,400 per month

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

    498 Marlboro Rd Unit S34, Brattleboro, VT 05301

    Property Id: 1510809One bedroom apartment for rent in a professionally managed apartment building in West Brattleboro, Vermont. Clean, bright, with on-site laundry and off-street parking. Rents include heat and hot water. All units are non smoking. Small pets would require approval and an additional security deposit.

    498 Marlboro Rd Unit S34, Brattleboro, VT 05301
  • /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
  • /7

    $1,700 per month

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

    4 Elliot St Unit 7, Brattleboro, VT 05301

    In town, one bedroom apartment, with bright sunlit rooms. The apartment is only three rooms and has a combined kitchen and living room, with a separate bedroom. This apartment is furnished. Coin operated laundry is on site, trash removal, and a secure building. Pet friendly building

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 7, Brattleboro, VT 05301
  • /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

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    1138 River Rd, Jamaica, VT 05343
  • /32

    $40,000 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
  • /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
  • /12

    $1,850 per month

    • 3 Beds
    • 1 Bath
    • 1,700 Sq Ft
    • Apartment for Rent

    1155 Putney Rd Unit 1A, Brattleboro, VT 05301

    Newly renovated second floor apt above local Restaurant. Conveniently located on the roundabout at Exit 3 of I-91. Great apartment with all new appliances, countertops, flooring, upgraded electrical and more. Easy location near shopping and restaurants. Non smokers and no pets. All utilities by tenant.

    Jim Bialowski BHG Masiello Keene

    1155 Putney Rd Unit 1A, Brattleboro, VT 05301
  • /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
  • /20

    $12,207 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
  • /32

    $35,000 per month

    • 4 Beds
    • 4 Baths
    • 3,500 Sq Ft
    • House for Rent

    896 Melendy Hill Rd, Londonderry, VT 05155

    PRICE REDUCTION!! Stunning, gorgeous, brand-new post-and-beam contemporary home for rent this season. Barely lived in, never rented. ALL NEW, EVERYTHING. THIS HOUSE SLEEPS 12+ VERY COMFORTABLY, SO COULD BE A GREAT IDEA FOR A 2 FAMILY SHARE.. LIVE IN PURE COMFORT AT A VERY REDUCED COST! this winter 4 bedrooms, all with en-suite bathrooms. Huge living room with 2-story windows facing east and

    Wilkie Bushby TPW Real Estate

    896 Melendy Hill Rd, Londonderry, VT 05155
  • /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
  • /12

    $2,200 per month

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

    4 Elliot St Unit 6, 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 6, Brattleboro, VT 05301
  • /19

    $65,000 per month

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

    16 Winterberry Heights, Stratton, VT 05360

    Best of the Best. Ski on Ski off. never rented before, pristine clean and original owners. Largest Treetops there is.. 4 bedroom/4 bath, den family room, amazing views, hot tub.. everything you want and need for an amazing winter season. Loads of room for family and guests and entertaining. Enjoy all that Stratton has to offer as well as all the other ski areas close by and Manchester shopping

    Wilkie Bushby TPW Real Estate

    16 Winterberry Heights, Stratton, VT 05360
  • /14

    $15,500 per month

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

    4591 Vermont 30, Jamaica, VT 05343

    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, full bath, laundry and family room with TV,

    Wilkie Bushby TPW Real Estate

    4591 Vermont 30, Jamaica, VT 05343
  • /13

    $1,800 per month

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

    995 Western Ave Unit 200, Brattleboro, VT 05301

    This full floor, renovated two-bedroom apartment is up a flight of steps on the 2nd floor. Amenities include eat-in kitchen with tile backsplash, dishwasher, windows on all sides, pantry or small office, a private, glassed-in porch with woods and mountain views, 1/2 open garage plus parking in the driveway for a second car, separate entrance, and a large backyard. Mowing, snow removal and heat

    995 Western Ave Unit 200, Brattleboro, VT 05301
  • /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
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