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Airbnb, Vacation rentals and hotel deals in Windsor County, VT

9.8 (95 reviews)
The Little Red Cabin! Less than 15 minutes to Okemo! Close to Everything VT!
Cabin · 2 Guests · 1 Bedroom
$150 /night*
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10 (26 reviews)
Beautiful Vacation Home with Spectacular Views
Holiday home · 2 Guests · 1 Bedroom
$425 /night*
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9.8 (44 reviews)
Beautiful Mountain Getaway for Skiing
Holiday home · 2 Guests · 1 Bedroom
$335 /night*
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10 (47 reviews)
Elegant Killington Condo with True Ski-on/Ski-Off.... Lodges A-103
Condo · 2 Guests · 1 Bedroom
$600 /night*
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9.6 (142 reviews)
New Lakeside Cottage near Okemo and Killington
Cottage · 2 Guests · 1 Bedroom
$260 /night*
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10 (64 reviews)
Stunning Lakeside home - ideal family getaway or work from home spot
Holiday home · 2 Guests · 1 Bedroom
$650 /night*
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Cozy Hartford Escape - Fire Pit, Near Skiing
Apartment · 2 Guests · 1 Bedroom
$380 /night
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8.7 (19 reviews)
The Lincoln Inn & Restaurant At The Covered Bridge
Inn · 2 Guests · 1 Bedroom
$190 /night
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10 (9 reviews)
Ski, hike, swim or relax with family & friends in this nature lovers delight!
Holiday home · 2 Guests · 1 Bedroom
$309 /night*
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9.1 (232 reviews)
The Quechee Inn at Marshland Farm
Inn · 2 Guests · 1 Bedroom
$157 /night
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9.3 (98 reviews)
Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel
Resort · 2 Guests · 1 Bedroom
$218 /night
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10 (27 reviews)
Sunrise Village/Bear Mountain, Ski Lift, Pool, Hot Tub and Gym, Sleeps 6, 3BR
Holiday home · 2 Guests · 1 Bedroom
$495 /night*
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Spacious Mountain Home Close to Killington and Woodstock
Holiday home · 2 Guests · 1 Bedroom
$307 /night
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10 (40 reviews)
Carriage House - 250 Private Acres; Views, Gardens, Skiing, Farm, Serenity
Holiday home · 2 Guests · 1 Bedroom
$250 /night*
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9.3 (276 reviews)
506 On the River Inn Woodstock
Accommodation · 2 Guests · 1 Bedroom
$289 /night
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9.6 (4 reviews)
Modern Farmhouse with Breathtaking River Views
Holiday home · 2 Guests · 1 Bedroom
$410 /night*
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8.4 (182 reviews)
The Shire Woodstock
Hotel · 2 Guests · 1 Bedroom
$190 /night
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9.2 (38 reviews)
Ski in/out Spruce Glen Townhomes on Great Eastern Trail
House · 2 Guests · 1 Bedroom
$543 /night
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9.0 (44 reviews)
Lake Rescue Chalet - 6-Bedroom Lake & Ski House with Hot Tub
Chalet · 2 Guests · 1 Bedroom
$550 /night*
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8.3 (203 reviews)
Align Inn Vermont
Hotel · 2 Guests · 1 Bedroom
$132 /night
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Airbnb, Log Cabin Rentals with Fireplace in Windsor County, VT

9.0 (44 reviews)
Lake Rescue Chalet - 6-Bedroom Lake & Ski House with Hot Tub
Chalet · 2 Guests · 1 Bedroom
$550 /night*
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9.6 (74 reviews)
Log Cabin home with Mt Ascutney views and pool table
Cabin · 2 Guests · 1 Bedroom
$367 /night*
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Inviting Vermont Cabin On Mount Ascutney!
Cottage · 2 Guests · 1 Bedroom
$431 /night
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What Are The Most Popular Amenities in Windsor County, VT?
Top Rental Amenities in Windsor County, VT
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Above shows the popular amenities in Windsor County and the number of the rental properties associated with each amenity. In Windsor County, 1245 rentals offer Internet or Wifi, 1216 rentals offer TV, 1161 rentals offer Bed linens provided. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Pets Friendly, Air Conditioning.
Which Price Range Is Considered As A Good Deal in Windsor County, VT Area?
Vacation House & Condo Rental Price Information in Windsor County, VT
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The graph shows the percentages of vacation homes in each price bucket. Windsor County has the largest percentage (15.88%) of homes in $150 - $200 price range.
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Which Accommodations Should I Pick in Windsor County, VT?
Best Accommodation Types in Windsor County, VT
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In Windsor County, 43.88% of listings are House, which is the most popular accommodation out of 19 total accommodation types. Avg price per night for House is around $372. And the most searched amenities for House accommodation is Pool.The least popular accommodation in Windsor County is Resort rentals
How Many Accommodations Are Pets Allowed in Windsor County, VT?
Percentage of Pet Friendly Rental Properties in Windsor County, VT
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24.93% of vacation homes in Windsor County are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
Which Airports Should I Choose To Get To Windsor County, VT?
Top Airports in Windsor County, VT
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Airbnb, Vacation House with Full Kitchen, and Other Rental Options in Windsor County, VT

Viewmont Chalet
Holiday home · 2 Guests · 1 Bedroom
$716 /night
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10 (30 reviews)
Reading Farms Estate
Holiday home · 2 Guests · 1 Bedroom
$4,625 /night*
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9.6 (93 reviews)
Luxury Ski House on Killington Mtn, 2 beds & Den w/ 3 en-suite baths, hot tub
Holiday home · 2 Guests · 1 Bedroom
$850 /night*
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Airbnb, Vacation House with Hot Tub in Windsor County, VT

Hakuna Matata - 10 Minutes to Killington Lifts
Holiday home · 2 Guests · 1 Bedroom
$543 /night
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Viewmont Chalet
Holiday home · 2 Guests · 1 Bedroom
$716 /night
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8.7 (3 reviews)
Fat Sheep Farm & Cabins
Farmhouse · 2 Guests · 1 Bedroom
$270 /night
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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