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Windham County, VT Rentals

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  • /8

    $1,850 per month

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

    3550 Coolidge Hwy Unit 2, Guilford, VT 05301

    Property Id: 1504084Find your peace in this adorable 1 bedroom, 2 bathroom unit in Guilford, VT. This second floor property at 3550 Coolidge Highway offers top amenities including full kitchen w/ gas range, washer/dryer, covered balcony, glass shower, storage, and more. Small dogs allowed, utilities included. Available now!

    3550 Coolidge Hwy Unit 2, Guilford, VT 05301
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    $2,100 per month

    • 2 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • House for Rent

    3292 Vt Route 100 N, Londonderry, VT 05148

    Beautifully maintained 2 bedroom home in South Londonderry, VT. Back patio to enjoy the immaculate gardens and the VT outdoors. 1st floor hosts a large eat in kitchen, livingroom, laundry room and full bath. 2nd floor has 2 oversized bedrooms with built-ins and a 3/4 bath. Tenant is responsible for all utilities and services. Credit Check and References required for move in.

    Team BVA Rentals Barrett and Valley Associates Inc.

    3292 Vt Route 100 N, Londonderry, VT 05148
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    $2,000 per month

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • House for Rent

    298 Sweet Pond Rd, Guilford, VT 05301

    Property Id: 23909593 Bedroom Ranch on 1-acre.Quiet location, beautiful country setting.5 miles from the Guilford Country Store.15 minutes to Brattleboro VT, 20 minutes to Greenfield, MA.Easy access to I-91 & Rte. 5UnfurnishedNew renovationsNew Exterior paint: Slate BlueOil, hot water baseboard heatingGas Range stoveWasher and dryer hook-ups in

    298 Sweet Pond Rd, Guilford, VT 05301
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    $2,500 per month

    • 2 Beds
    • 1 Bath
    • 1,456 Sq Ft
    • House for Rent

    85 Parker Hill Rd, Bellows Falls, VT 05101

    Rare chance to rent a stand-alone, two-bedroom home, privately located on a tranquil seven-acre lot. Open fields surround the house and a pathway leads down to a swimming hole under a railroad trestle on the Williams River. The home features an open-concept kitchen with a center island, a living room with hardwood floors and cathedral ceilings with a woodstove with brick hearth, and a dining area

    Steve Schoppmeyer BHG Masiello Brattleboro

    85 Parker Hill Rd, Bellows Falls, VT 05101
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    $8,767 per month

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

    3A Black Pine Unit SI ID1261564P, Dover, VT 05356

    The advertised rate of $8,768/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 19, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    3A Black Pine Unit SI ID1261564P, Dover, VT 05356
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    $2,200 per month

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

    4 Elliot St Unit 5, Brattleboro, VT 05301

    Corner apartment in downtown Brattleboro in the National is located on the corner of Elliot and Main Street. This two-bedroom apartment is in a secure building, laundry facilities on site, with parking down the street in the parking garage. Pets are welcome with an extra pet fee.

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 5, Brattleboro, VT 05301
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    $1,350 per month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    498 Marlboro Rd Unit S35, Brattleboro, VT 05301

    Property Id: 15108101 bed, 1 bath apartment in Brattleboro, VT! This unit features modern amenities like a microwave, oven, and refrigerator. Enjoy off-street parking, on-site laundry, and a beautiful lawn. Pets are welcome! Don't miss out on this gem for $1,350/month. Book your viewing today!

    498 Marlboro Rd Unit S35, Brattleboro, VT 05301
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    $2,300 per month

    • 2 Beds
    • 1 Bath
    • 930 Sq Ft
    • Townhouse for Rent

    60 Brookside Dr Unit 3, Brattleboro, VT 05301

    This warm and inviting 2-bedroom condo comes fully furnished with everything you will need to just move in and relax. The first-floor open concept kitchen/living room makes for easy entertaining while you cook dinner. Upstairs are both bedrooms and the 3/4 bathroom. This comes with a full basement that has the washer and dryer and still usable space for storage or another room. This condo is not

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    60 Brookside Dr Unit 3, Brattleboro, VT 05301
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    $1,400 per month

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

    210 Elliot St Unit 3, Brattleboro, VT 05301

    210 Elliot St Unit 3, Brattleboro, VT 05301
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    $22,000 per month

    • 3 Beds
    • 2 Baths
    • 2,255 Sq Ft
    • House for Rent

    378 Tuttle Hill Rd, Londonderry, VT 05155

    Get ahead of the '26-'27 ski season with this turnkey mountain modern gem. Fully renovated with attention to detail, this cheerful, sunny Scandinavian Modern space welcomes and inspires. 15 minutes to Stratton Base, 14 minutes to Bromley Village, and 10 minutes to Magic Mountain, you are in the middle of it all, with your choice to either explore or stick to your home mountain. The main floor

    Jamie Luke TPW Real Estate

    378 Tuttle Hill Rd, Londonderry, VT 05155
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    $1,925 per month

    • 1 Bed
    • 1.5 Baths
    • 835 Sq Ft
    • Condo for Rent

    18 Henry St Unit Townhouse-like Apartment, Bellows Falls, VT 05101

    18 Henry St Unit Townhouse-like Apartment, Bellows Falls, VT 05101
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    $1,700 per month

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

    4 Elliot St Unit 2, Brattleboro, VT 05301

    Corner apartment in downtown Brattleboro in the National is located on the corner of Elliot and Main Street. This one-bedroom apartment is in a secure building, laundry facilities on site, with parking down the street in the parking garage. Pets are welcome with an extra pet fee.

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 2, Brattleboro, VT 05301
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    $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
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    $1,600 per month

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

    118 Vt Route 30 Unit 1, Newfane, VT 05345

    Sweet first-floor apartment in fantastic location! Clean and ready for new occupant. Apartment features open concept living space, recessed lighting and over-sized windows. Bonuses include laundry room, covered parking and bonus of electric car charging port. Fresh interior paint and carpet cleaning after change of tenant. An easy 15-minute commute to Brattleboro and I-91. Low maintenance as rent

    Jessica Landers Barrett and Valley Associates Inc.

    118 Vt Route 30 Unit 1, Newfane, VT 05345
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    $1,600 per month

    • 2 Beds
    • 1 Bath
    • 1,250 Sq Ft
    • Condo for Rent

    92 Prospect St Unit 1, Brattleboro, VT 05301

    Close to downtown Brattleboro.2 bedroom, beautiful wood floors, Covered porch, pantry, non-working fireplace, 2 parking spaces.Heat, Hot Water, Dumpster on site, Plowing included in rent. Tenants pay all utilities - Electricity/Cable/Internet.$1600/month - First and security deposit required.

    92 Prospect St Unit 1, Brattleboro, VT 05301
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    $1,550 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
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    $2,100 per month

    • 2 Beds
    • 1.5 Baths
    • 1,100 Sq Ft
    • Condo for Rent

    238 Fairview St Unit 238 Fairview Street, Brattleboro, VT 05301

    This is a completely renovated three story furnished duplex built in 1932 with a renter on the other side. The renovation included removing the traditional kitchen and dining room, opening up the first floor space to include a galley kitchen with a marble island, a cozy sitting area with a propane stove, a half bath, and a comfortable living room space. The second floor has a small laundry room,

    238 Fairview St Unit 238 Fairview Street, 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
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    $1,950 per month

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

    995 Western Ave Unit 100, Brattleboro, VT 05301

    This 2-bedroom apartment is just being renovated and is freshly painted. Amenities include an eat-in kitchen, new dishwasher and refrigerator, pantry, new or refinished flooring throughout, new bathroom, new windows, large screened porch, 1/2 garage plus parking for a second car in the driveway, separate entrance, and a large backyard with room to garden. Mowing, snow removal and heat are

    995 Western Ave Unit 100, Brattleboro, VT 05301
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    $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
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    $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
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    $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
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    $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
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    $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
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    $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
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    $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
  • /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
  • /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
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    $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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