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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.

Living room of a luxury seasonal rental at Woodstock, Vermont. Stylish carpet in purple and blue tones. Sun coming in from large windows with a view of the Green Mountains.

Winter 2024–2025 Rental
Woodstock 4 Bedrooms | 5 Bathrooms | 12 Guests

Modern rental studio in Killington with queen bed, sleeper sofa and ceiling fan.

Winter 2024–2025 Rental
Killington Studio | 1 Bathroom | 4 Guests

Well-equipped kitchen in light wooden colors. Ceiling fan in bronze.

Winter 2024–2025 Rental
Rutland, near Pico & Killington 2 Bedrooms | 1 Bathroom | 4 Guests

Front of a large multi-floor house in Vermont. Lots of green and sun around it.

Winter 2026 Rental
North Chittenden / Pittsford 4 Bedrooms | 3.5 Bathrooms

Living room of a seasonal rental in Killington, Vermont. High ceiling and lots of light from many windows. Sofa and kitchen island with plentiful seating.

Summer 2025 Rental
Killington 6 Bedrooms | 6 Bathrooms | 8 Guests

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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Winter exterior view of a condo complex near the slopes at the Killington ski resort in Vermont.

Killington Seasonal Rentals

Living room of a luxury vacation home with black-leather armchairs and an mosaic of windows. The Vermont landscape seen outside the windows.

Luxury Rentals Killington, VT

Nicely-decorated vacation-rental property with a large window and sofa. Trees seen outside the window.

Property Management

Interior of a luxurious rental home in Woodstock, Vermont. Large windows with a view of the Green Mountains.

Woodstock Seasonal Rentals

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.

Killington
Welcome to The Behnke Family Retreat at Mt. Green Resort in Killington, VT! Just steps from Killington Ski Resort, this cozy 1BR/1BA condo is perfect for mountain getaways.

Mountain Green 3D23

  • 1 Bedroom
  • 1 Bathroom
  • 4 Guests
Killington
The Bigelow Chalet in Killington, Vermont, is a spacious pet-friendly, multi-level property ideal for large groups, featuring 8 bedrooms, 4.

Bigelow Chalet at Killington

  • 8 Bedrooms
  • 4.5 Bathrooms
  • 16 Guests
Killington
Welcome to your next vacation haven! Nestled in the scenic Mountain Green Resort in Killington, Vermont, our 2-bedroom, 2-bathroom loft condo offers the perfect blend of comfort and convenience for your getaway.

Mountain Green 3G6

  • 2 Bedrooms
  • 2 Bathrooms
  • 6 Guests
Killington
This luxurious 4-bedroom, 4-bathroom home at The Vistas at Sunrise in Killington, Vermont, offers a perfect blend of comfort and adventure.

Vistas 92

  • 4 Bedrooms
  • 4 Bathrooms
  • 8 Guests
Killington
Experience the ultimate Killington escape at Sunrise Timberline M1, a charming ski-in, ski-out condo that perfectly blends comfort and adventure.

Sunrise Timberline M1

  • 2 Bedrooms
  • 2 Bathrooms
  • 6 Guests
Killington
Escape to the Trail Creek Suite in Killington, VT, your perfect mountain getaway! This charming 1-bedroom condo, with a queen bedroom and cozy twin in the living room, welcomes up to 3 guests into a warm, inviting space complete with a crackling fireplace.

Trail Creek #13

  • 1 Bedroom
  • 1 Bathroom
  • 3 Guests
Killington
Welcome to your perfect getaway at Killington Center Inn and Suites in Killington, Vermont! This renovated hotel-style studio is designed for comfort and convenience, ensuring a memorable stay.

Killington Center #523

  • Studio
  • 1 Bathroom
  • 4 Guests
Killington
QUIET, WOODED PROPERTY ON KILLINGTON BORDER, minutes from slopes! Peak Hill is a newly rebuilt ski home on the border of Killington and Pittsfield, Vermont and close to all the activity! This home features three bedrooms, two full bathrooms, living room, kitchen, large deck and outdoor area.

Peak Hill Home

  • 3 Bedrooms
  • 2 Bathrooms
  • 6 Guests
Killington
Killington Vista is a charming five bedroom, three bathroom home located in the heart of Killington. This three floor home features every amenity you could want including hot tub, sauna, game room, media room, streaming TVs, Alexa, professional bubble hockey, foosball, fireplace and large outdoor deck with mountain views.

Tanglewood Vista at Killington

  • 5 Bedrooms
  • 3 Bathrooms
  • 14 Guests
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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