Bennington County, VT Rentals

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  $40,000 per month

  • 4 Beds
  • 3 Baths
  • 2,791 Sq Ft
  • House for Rent

  33 Strattonwald Rd, Winhall, VT 05340

  Lock in your rental for next year! This cheerful, modern-yet-classic Strattonwald chalet is nestled in a private community just 9 minutes to Stratton's Main Base, with shuttle access. There is so much room for everyone, with two primary bedroom suites plus two more bedrooms; a gourmet open-concept kitchen/dining/living room with wood stove; second living/TV room; and downstairs game room with bar

  Jamie Luke TPW Real Estate

  33 Strattonwald Rd, Winhall, VT 05340
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  $1,300 per month

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

  178 S Branch St Unit 178, Bennington, VT 05201

  Second floor two bedroom in quiet neighborhood.- two good sized bedrooms, each with closet- living room- eat in kitchen with new floor- bathroom with shower stall- new windows- newer carpet / newly painted- great quiet neighborhood but still close to downtown- propane heat (tenant pays)- off peak electric hot water (tenant pays)- property owner pays for

  178 S Branch St Unit 178, Bennington, VT 05201
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  $1,295 per month

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

  201 Division St Unit 201, Bennington, VT 05201

  Property Id: 2255313This freshly painted, recently renovated 2 bedroom unit, located in a nice neighborhood near downtown, is now available! 1295/month rent. Washer and Dryer hookups in the unit. Heat pump system with multiple heads handles the heat and cooling. Water/Sewer and trash, but not heat, included in the rent as well as one parking space. Owner is willing to consider pets with a

  201 Division St Unit 201, Bennington, VT 05201
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  $6,000 per month

  • 3 Beds
  • 3 Baths
  • 2,425 Sq Ft
  • House for Rent

  3436 Main St, Manchester, VT 05254

  Summer Rental | July 1 – October 15, 2026 Winter Rental | December 2026 - March 2027Offered for the first time, this exceptional Manchester residence presents a rare opportunity to enjoy refined village living in the heart of Manchester, Vermont. Beautifully renovated and fully furnished, the home artfully blends timeless elegance with modern sophistication.At the center of the home is a

  

  Kristin Comeau

  TPW Real Estate

  (802) 474-3905

  3436 Main St, Manchester, VT 05254
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  $2,700 per month

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • House for Rent

  127 Mountain Ridge Rd, Peru, VT 05152

  If you're looking for a year-round rental in the Peru/Londonderry area, this contemporary mountain home has so much to offer. The inviting open-concept layout features a kitchen, living and dining space that extends out to a charming sun porch and back deck. Nestled close to Flood Brook, Bromley, and all that Londonderry and Peru have to offer, the location is convenient. And across the street

  Jamie Luke TPW Real Estate

  127 Mountain Ridge Rd, Peru, VT 05152
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  $1,300 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  172 S Branch St Unit 172, Bennington, VT 05201

  First floor two bedroom- walk to town- living room, dining room, kitchen, full bathroom with shower stall, comes with newer electric stove and fridge, washer/dryer hookups- heat is forced hot air (fuel oil)- rent DOES NOT INCLUDE utilities- I pay for lawncare, plowing and garbage- I take first month's rent, last month's rent and one month's rent as a security deposit (3x

  172 S Branch St Unit 172, Bennington, VT 05201
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  $1,400 per month

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

  40 Rootville Rd Unit 40A, Manchester Center, VT 05255

  $1,400 / 1br - 900ft2 - Manchester Vermont one bedroom (Manchester)Manchester VT One bedroom apartment , approximately 900 square feet , all on one floor , highly efficient with air conditioning. A one car garage and driveway parking for two cars. One bedroom apartment. Available February 1st. $1,400 a month - utilities not included. Manchester one and a half miles to the center of

  40 Rootville Rd Unit 40A, Manchester Center, VT 05255
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  /23

  $7,000 per month

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft
  • House for Rent

  65 Cranberry Hill Rd, Bondville, VT 05340

  Never before offered: This Strattonwald contemporary ski house is a well cared-for home base for all who love the mountain lifestyle, in a private woodland setting just 9 minutes to Stratton's Main Base. The expansive living room is the ultimate gathering spot from morning to night, with soaring cathedral ceilings, a super-cozy wood stove, and extraordinary windows looking out at the private

  Jamie Luke TPW Real Estate

  65 Cranberry Hill Rd, Bondville, VT 05340
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  $2,200 per month

  • 2 Beds
  • 2.5 Baths
  • 1,265 Sq Ft
  • House for Rent

  212 Dewey St, Bennington, VT 05201

  This property is available now, and is fully furnished. Water/sewer included. The whole interior of the home has just been repainted in the last couple of years. Wood floors sanded. New stove. New Washer and Dryer, new flooring in the kitchen. Two bedrooms, 2.5 baths. The basement holds huge potential for storage. Small back deck to enjoy the creek. Two car garage. Just take a look at the photos

  212 Dewey St, Bennington, VT 05201
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  $1,575 per month

  • 3 Beds
  • 1.5 Baths
  • 980 Sq Ft
  • House for Rent

  218 Abbott St, Bennington, VT 05201

  Please don't click the "Request To Apply" button as it will cause a delay in our ability to respond to you. Read below for instructions on how to apply.3br MANUFACTURED HOME for rent!Unit: A-218Apply To: Mountain View CommunityRent: $1575/moBeds/Baths: 3 beds 1.5 bathsSize: 980 square feetPets: Cat & Dog friendly, all animals must be approved. Pet deposit not

  218 Abbott St, Bennington, VT 05201
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  $850 per month

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

  318 School St Unit 125 Adams, Bennington, VT 05201

  318 School St Unit 125 Adams, Bennington, VT 05201
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  $2,300 per month

  • 2 Beds
  • 1 Bath
  • 1,018 Sq Ft
  • Condo for Rent

  214 Coombs Rd Unit 214, Manchester Center, VT 05255

  Carefree Living in the Heart of Manchester EastEnjoy the perfect blend of comfort and convenience in this spacious, one-level condominium. Located in the highly sought-after Manchester East community, this home is designed for those who want to spend less time on chores and more time enjoying everything the area has to offer. Key FeaturesSpacious Layout: Two bright bedrooms and one full

  Robin Apps Four Seasons Sotheby's Int'l Realty

  214 Coombs Rd Unit 214, Manchester Center, VT 05255
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  $1,550 per month

  • 3 Beds
  • 1.5 Baths
  • 924 Sq Ft
  • House for Rent

  36 W Road Park, Woodford, VT 05201

  Please don't click the "Request To Apply" button as it will cause a delay in our ability to respond to you. Read below for instructions on how to apply.3br MANUFACTURED HOME Available for rent!Unit: 36Apply To: West Road CommunityRent: $1550/moBeds/Baths: 3 beds 1.5 bathsSize: 924 square feetPets: Cat & Dog friendly, all animals must be approved. Pet deposit

  36 W Road Park, Woodford, VT 05201
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  $1,550 per month

  • 3 Beds
  • 1.5 Baths
  • 924 Sq Ft
  • House for Rent

  47 Dudley Plaza, Woodford, VT 05201

  Please don't click the "Request To Apply" button as it will cause a delay in our ability to respond to you. Read below for instructions on how to apply.3br MANUFACTURED HOME for rent!Unit: D-047Apply To: Mountain View CommunityRent: $1550/moBeds/Baths: 3 beds 1.5 bathsSize: 926 square feetPets: Cat & Dog friendly, all animals must be approved. Pet deposit not

  47 Dudley Plaza, Woodford, VT 05201
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  $2,750 per month

  • 2 Beds
  • 2 Baths
  • 1,910 Sq Ft
  • House for Rent

  477 Myers Rd, Shaftsbury, VT 05262

  Charming circa 1910 two-bedroom unfurnished Vermont Farmhouse in the town of Shaftsbury. Located on a town-maintained road, non-smoking, no pet property, with parking limited to two cars. The included appliances are a washer, dryer, refrigerator, and electric stove. All showings will be scheduled for Wednesday and Thursday afternoons only.

  

  Kristin Comeau

  TPW Real Estate

  (802) 520-0672

  477 Myers Rd, Shaftsbury, VT 05262
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  $1,350 per month

  Apartment for Rent

  1 Bed

  87 Cone Rd, Manchester Center, VT 05255

  12 Month Lease, $1,350 deposit, Available NowRoomy 1 bedroom apartments located on a quiet dead end road near the center of town. Open living, dining and kitchen area, washer and dryer, air conditioning, patio. No pets, no smoking. $1,350.00/month plus utilities. One year lease, first, last and security due on signing.87 Cone Rd is an apartment community located in Bennington

  87 Cone Rd, Manchester Center, VT 05255
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  $10,000 per month

  • 4 Beds
  • 3 Baths
  • 5,624 Sq Ft
  • House for Rent

  37 Burnt Hill Rd, Winhall, VT 05340

  MARCH 2026 ONLY. Location, Stratton ski shuttle, style, and so much space: Welcome to your mountain home! This luxurious Strattonwald home offers bedrooms for the whole crew, plus loads of living space, light, a well-equipped, gourmet kitchen for cooking and entertaining, and a hot tub for après-ski memories. It is well-built, lovingly cared-for, and a rare opportunity to rent for just one month

  Jamie Luke TPW Real Estate

  37 Burnt Hill Rd, Winhall, VT 05340
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  /19

  $4,000 per month

  • 4 Beds
  • 1.5 Baths
  • 1,404 Sq Ft
  • House for Rent

  937 Route 30, Dorset, VT 05251

  Welcome home! This beautiful and well maintained 4 bedroom, 1.5-bath home is in the charming town of Dorset. It offers over 1,404 sq feet of single-story living. This very well thought out and comfortable floor plan features a bright, large living and dining room and many windows throughout the entire house. A separate dining area perfect for gatherings. Enjoy the outdoors on the large back deck

  Martina Dvorak-Grattan Wohler Realty Group

  937 Route 30, Dorset, VT 05251
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  /19

  $35,000 per month

  • 3 Beds
  • 3 Baths
  • 2,920 Sq Ft
  • House for Rent

  2 Aspen Ln, Winhall, VT 05340

  *Available for a partial season discount.* Stratton views, sunlight, space, and location: this ski chalet has it all! The open floor plan of the main level brings everyone together around the spacious kitchen, dining area, and living room, under a vaulted cathedral ceiling and with a wall of windows overlooking the forest below and Stratton's peak ahead. Front deck offers dining area and a grill

  Jamie Luke TPW Real Estate

  2 Aspen Ln, Winhall, VT 05340
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  $10,000 per month

  • 5 Beds
  • 3.5 Baths
  • 4,017 Sq Ft
  • House for Rent

  11 Founders Hill Rd, Winhall, VT 05360

  Stratton Mountain location for full time or vacation style living! Spacious home that you can walk to Village, gondola, golf and Sports center. Corner lotjust down the street from the Stratton Mountain Club and the Base Lodge. Home has five bedrooms with a chefs kitchen that has Viking Stove, ice-maker and three dishwashers for entertaining guests. Living room and dining room are graced with

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  11 Founders Hill Rd, Winhall, VT 05360
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  $1,350 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Condo for Rent

  254 Union St Unit B, Bennington, VT 05201

  Second Floor Renovated Two Bedroom Apartment- second floor 2 bedroom, each bedroom has a closet- renovated, new windows and entry door- washer/dryer hookups in kitchen- new stove, new fridge- egress windows and carbon monoxide detectors- includes heat, garbage, plowing and lawncare- tenant pays hot water (electric) and electric - all new!- walk to all amenities,

  254 Union St Unit B, Bennington, VT 05201
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  $4,600 per month

  • 3 Beds
  • 1.5 Baths
  • 1,948 Sq Ft
  • House for Rent

  10 Rocky Rd, Winhall, VT 05340

  Location, location location..... This three-bedroom gem is located in one of the most desirable areas in the tri-mountain area. Centrally located between Stratton and Manchester; you will find yourself less than a 15-minute drive to each. Bromley is around the corner. The perfect chalet to come home to after a fun day of skiing. Sit by the roaring fire with a cup of cocoa and

  Peggy O'neill Cummings & Co

  10 Rocky Rd, Winhall, VT 05340
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  /20

  $5,800 per month

  • 3 Beds
  • 2 Baths
  • 2,348 Sq Ft
  • House for Rent

  8 Rocky Rd, Winhall, VT 05340

  Located in one of the most sought-after spots in the area. This three-bedroom "mid-century vibed" beauty is just a 10-minute drive to the Stratton Access Road and a 12-minute drive to Manchester. Bromley is literally around the corner and Magic is a quick 15-minute drive.There is a beautiful stream in the backyard that adds additional "802" ambiance to the property. Truly a peaceful setting

  Peggy O'neill Cummings & Co

  8 Rocky Rd, Winhall, VT 05340
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  /23

  $28,000 per month

  • 4 Beds
  • 3 Baths
  • 2,406 Sq Ft
  • House for Rent

  35 Strattonwald Rd, Winhall, VT 05340

  $28,000 Winter Rental Rate | Spend the winter in Vermont at this inviting 4-bedroom, 3-bath Strattonwald chalet, available mid-November through mid-April. Nestled among the woods yet just minutes from Stratton Mountain, this home offers a welcoming retreat and the perfect base for the ski season. The main living area features soaring vaulted ceilings and a pellet stove, creating a bright and cozy

  Cheyanne Pugliese

  35 Strattonwald Rd, Winhall, VT 05340
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  $1,275 per month

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

  18 Main St Unit C, North Bennington, VT 05257

  Centrally located 3 family house with awesome tenants and awesome neigbors.

  18 Main St Unit C, North Bennington, VT 05257
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  $1,650 per month

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

  9 Church St Unit 9 Church St, North Bennington, VT 05257

  Beautifully maintained 2 bedroom unit (half of a duplex) in desirable North Bennington. Heat included with rent.Credit and background checks required. First and security due at lease signing. Sorry no smoking, and no pets.

  9 Church St Unit 9 Church St, North Bennington, VT 05257
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  $1,500 per month

  • 2 Beds
  • 1.5 Baths
  • 852 Sq Ft
  • Condo for Rent

  432 South St Unit B4, Bennington, VT 05201

  Discover a delightful living experience at 432 South St. Unit B4, a welcoming 2-bedroom, 1.5-bathroom condo nestled in the highly sought-after Nathaniel Court neighborhood of Bennington, VT. Enjoy a range of amenities, including laundry hookups, a dedicated parking space, lawn care, plowing, and garbage taken care of by the association. Please note that pet will not be considered and smoking

  432 South St Unit B4, Bennington, VT 05201
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  $995 per month

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

  302 Silver St Unit 304.5, Bennington, VT 05201

  Thiis is a four unit right in town with great considerate tenants.

  302 Silver St Unit 304.5, Bennington, VT 05201
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  $5,000 per month

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft
  • House for Rent

  397 Powderhorn Rd, Manchester Center, VT 05255

  SPRING/SUMMER RENTAL: Charming newly renovated ranch with 3 bedrooms, 2 baths is the perfect summer rental, offering a cozy and inviting atmosphere! Conveniently located close to town for easy access to shops and dining. Enjoy a fenced-in backyard with a deck, perfect for grilling and outdoor relaxation. The kitchen and living room are located on the first floor, along with the spacious primary

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 729-7527

  397 Powderhorn Rd, Manchester Center, VT 05255
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  $6,500 per month

  • 4 Beds
  • 3.5 Baths
  • 2,340 Sq Ft
  • House for Rent

  294 Green Peak Orchard S, Dorset, VT 05253

  Escape to a stunning summer/winter retreat in Southern Vermont, featuring 4 spacious bedrooms and 3.5 baths. Nestled in the heart of nature, this property offers breathtaking mountain views, perfect for relaxation and outdoor adventures. Open-concept living/kitchen area with plenty of seating, a wood burning fireplace, and panoramic mountain views. Kitchen is fully equipped with modern

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 644-7034

  294 Green Peak Orchard S, Dorset, VT 05253
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  $1,250 per month

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  180 Northbranch St Unit B, Woodford, VT 05201

  180 Northbranch St Unit B, Woodford, VT 05201
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  $8,000 per month

  • 3 Beds
  • 3 Baths
  • 1,980 Sq Ft
  • House for Rent

  3093 Route 30, Dorset, VT 05251

  Wonderful Dorset Village Historic Colonial, private and completely protected by the established vintage tree line that buffers the neighbors and Route 30. Walk to Village location, this property has been fully renovated with updated kitchen and baths. The house is warm and welcoming with front and side covered porch entrance while the rear screened porch creates an expansive summer room to the

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 255-8729

  3093 Route 30, Dorset, VT 05251
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  $12,500 per month

  • 4 Beds
  • 4.5 Baths
  • 4,393 Sq Ft
  • House for Rent

  163 Taconic Rd, Manchester, VT 05255

  Exclusive Taconic Avenue walk to Village Location... Rarely found, Recently Constructed in 2002 this High Country Colonial is on one acre seamlessly blending within the historic district. Aesthetically pleasing among the area's recently restored Houses of the Hildene era, this residence meets all expectations! Deep front porch entry to soaring foyer flanked with formal rooms while the family

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 255-8917

  163 Taconic Rd, Manchester, VT 05255
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  $1,750 per month

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Condo for Rent

  9 Mechanic St Unit B, North Bennington, VT 05257

  9 Mechanic St Unit B, North Bennington, VT 05257
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  $1,275 per month

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

  18 Main St Unit C, North Bennington, VT 05257

  Centrally located 3 family house with awesome tenants and awesome neigbors.

  18 Main St Unit C, North Bennington, VT 05257
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  $1,500 per month

  • 1 Bed
  • 1 Bath
  • House for Rent

  126 Simeon Dean Rd, Shaftsbury, VT 05262

  Property Id: 1215378Oak Tree Farm is a beautifully restored 1800's colonial farm house. The apartment is upstairs and has a private entrance. The area is quite and the views are tranquil. From the upstairs apartment you will have a water view of our 6 acre pond, horse's and rescue donkies! The apartment has all the charm of an older restored 1800's colonial farm house. It has wide

  126 Simeon Dean Rd, Shaftsbury, VT 05262
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  $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
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  $3,850 per month

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • House for Rent

  1180 N Rd, Sunderland, VT 05252

  Property Id: 1573034Have your own slice of quintessential Vermont with this 3 acre property at the base of the Green Mountains. A lush, wooded, private property, you will love this 4 bed, 2.5 bath Sunderland home. The 1st floor is an open floor plan with plenty of natural light with a bonus recreational room/office and half bath. The kitchen has granite counters with an updated faucet and

  1180 N Rd, Sunderland, VT 05252
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  $11,300 per month

  • 5 Beds
  • 3 Baths
  • 4,432 Sq Ft
  • House for Rent

  303 W View Estates, Manchester, VT 05255

  Gorgeous 4,432 Square Foot - 5 bedroom, 3 bath Log Home in the Heart of Manchester and the Green Mountains! You won't find a better equipped, more spacious and luxury home, located in one of the best Winter and Summer vacation spots in Vermont. 1st Floor boasts a beautiful great room with cathedral ceiling, stone fireplace seamlessly flows into an open-concept kitchen/dining area. Great for

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 300-4671

  303 W View Estates, Manchester, VT 05255
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  $30,000 per month

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft
  • Townhouse for Rent

  90 Turkey Run Rd, Winhall, VT 05340

  Intervale Rental. Available for the winter 25-26 winter season. Also available for summer or fall monthly rental. Entry mud room for boot storage. Main floor has wood burning fire place, and the deck off the living room is a overlooks the pond. Main floor has primary suite. Two bedrooms plus a sleeping loft on the upper floor. One bedroom has an en suite bathroom, and a hallway full bathroom

  Christiane Carroccio TPW Real Estate

  90 Turkey Run Rd, Winhall, VT 05340

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