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Vermont Seasonal Rentals

Experience Vermont like a local with a seasonal rental that offers all the comforts of home for an extended stay. Whether you’re here for the vibrant fall foliage, winter skiing, or the tranquil summers, a fully-furnished extended stay lets you settle in and savor the best of the Green Mountain State. Book with us to enjoy space, privacy, great locations, and the flexibility to explore Vermont at your own pace.

Featured Winter Seasonal Rental

Contemporarily-decorated guest house at seasonal rental. Large windows with panoramic views of Woodstock, VT.

Luxurious Casita Alta in Woodstock, VT

  • Main house + guest house + heated outdoor pool for the winter season!
  • Spacious 3400 ft2 main house with 3 floors.
  • 4 bedrooms / 5 bathrooms / Sleeps 12.
  • Stunning mountain views from nearly every room, the pool, and the balcony.
  • Main floor:
    • Open living, dining, and kitchen area, fireplace, 16-foot balcony for sunset views.
    • King master suite with private bath, shower, and jacuzzi.
    • Spacious, gourmet kitchen with high-end appliances.
    • Half bathroom & mudroom.
  • Available for seasonal rental from November 1 to May 1.

Tastefully Decorated and Full of Light

  • Private 20 x 40 ft outdoor heated pool, doubles as an extra-large hot tub!
  • Ground level floor:
    • Bedroom with king and queen beds.
    • Bathroom.
    • Space for working out, yoga, or air hockey.
    • Dedicated office space with a printer and an Apple desktop computer.
  • Top floor:
    • Bedroom with 2 full-size beds, private bathroom, and books and toys to entertain kids.
    • Unique balcony with sunset views.

Beautiful Guest House with Stunning Views

  • Includes a 1000 ft2 guest house with exotic Brazilian wood finishes and panoramic mountain views from 10-foot windows!
  • Guest house features a spacious living/dining/kitchen area, luxurious wood decking, and a Murphy full bed.
  • Ideal for stargazing with clear views of the Milky Way.
  • The property is a short 0.5-mile walk to downtown Woodstock, offering a peaceful yet convenient retreat.
  • Only 0.2 miles to East Park for outdoor activities.
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Contemporarily-decorated guest house at seasonal rental. Large windows with panoramic views of Woodstock, VT.
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Comfortable Studio at Killington Center Inn & Suites

  • Charming second-floor studio in a prime Killington location.
  • Features a cozy queen bed and an additional sleeper sofa for extra comfort.
  • Kitchenette equipped with a microwave, mini fridge, sink, and all essentials for light cooking and snacks.
  • Counter-height table, ideal for dining for two.
  • Private bathroom with a shower.
  • Air conditioning (heating and cooling).
  • Smart TV, high-speed Wi-Fi, and keyless smart locks.
  • Available for seasonal rentals from November 15 to May 15 for $10,000, with end-of-stay cleaning included (utilities covered).

The Ideal Base for your Killington Getaway

  • Convenient location along the bus route to Killington Resort—reach the slopes with ease!
  • Many dining and nightlife options close by, including The Rivershed Killington, The Foundry at Summit Pond, and Back Country Cafe, all at walking distance.
  • Killington Center Inn & Suites holds a 97% average customer satisfaction rating based on guest feedback.
  • (Please note: The studio is accessible via one flight of stairs.)
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Other Vermont Properties

The properties shown above are tailored for full-season rentals, offering the ideal setup for those looking to stay in Vermont for most of the season. If you are planning to stay for a month or two, or for one or more shorter periods, explore our portfolio of regular Vermont vacation rentals. Simply enter your dates on the page to see available units. Prices will reflect the full period selected. A few examples follow.

Cabin in a beautiful Vermont scenery, presumably a vacation rental that receives competent property management.

SIMPLE, Inc VACATION RENTALS

Give Us A Call At:

802-736-7467

SIMPLE, Inc VACATION RENTALS

Give Us A Call At:802-736-7467

CONTACT US

505 Killington Rd
Killington, VT 05751


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