Airbnb, Cabins, Vacation Rentals in Windsor County, VT
Compare 2,680 available, short term vacation home properties, starts from $18
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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*
10 (26 reviews)
Beautiful Vacation Home with Spectacular Views
Holiday home · 2 Guests · 1 Bedroom
$425 /night*
9.8 (44 reviews)
Beautiful Mountain Getaway for Skiing
Holiday home · 2 Guests · 1 Bedroom
$335 /night*
10 (47 reviews)
Elegant Killington Condo with True Ski-on/Ski-Off.... Lodges A-103
Condo · 2 Guests · 1 Bedroom
$600 /night*
9.6 (142 reviews)
New Lakeside Cottage near Okemo and Killington
Cottage · 2 Guests · 1 Bedroom
$260 /night*
10 (64 reviews)
Stunning Lakeside home - ideal family getaway or work from home spot
Holiday home · 2 Guests · 1 Bedroom
$650 /night*
Cozy Hartford Escape - Fire Pit, Near Skiing
Apartment · 2 Guests · 1 Bedroom
$380 /night
8.7 (19 reviews)
The Lincoln Inn & Restaurant At The Covered Bridge
Inn · 2 Guests · 1 Bedroom
$190 /night
10 (9 reviews)
Ski, hike, swim or relax with family & friends in this nature lovers delight!
Holiday home · 2 Guests · 1 Bedroom
$309 /night*
9.1 (232 reviews)
The Quechee Inn at Marshland Farm
Inn · 2 Guests · 1 Bedroom
$157 /night
9.3 (98 reviews)
Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel
Resort · 2 Guests · 1 Bedroom
$218 /night
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*
Spacious Mountain Home Close to Killington and Woodstock
Holiday home · 2 Guests · 1 Bedroom
$307 /night
10 (40 reviews)
Carriage House - 250 Private Acres; Views, Gardens, Skiing, Farm, Serenity
Holiday home · 2 Guests · 1 Bedroom
$250 /night*
9.3 (276 reviews)
506 On the River Inn Woodstock
Accommodation · 2 Guests · 1 Bedroom
$289 /night
9.6 (4 reviews)
Modern Farmhouse with Breathtaking River Views
Holiday home · 2 Guests · 1 Bedroom
$410 /night*
8.4 (182 reviews)
The Shire Woodstock
Hotel · 2 Guests · 1 Bedroom
$190 /night
9.2 (38 reviews)
Ski in/out Spruce Glen Townhomes on Great Eastern Trail
House · 2 Guests · 1 Bedroom
$543 /night
9.0 (44 reviews)
Lake Rescue Chalet - 6-Bedroom Lake & Ski House with Hot Tub
Chalet · 2 Guests · 1 Bedroom
$550 /night*
8.3 (203 reviews)
Align Inn Vermont
Hotel · 2 Guests · 1 Bedroom
$132 /night
Airbnb, Log Cabin Rentals with Fireplace in Windsor County, VT
Fireplace
9.0 (44 reviews)
Lake Rescue Chalet - 6-Bedroom Lake & Ski House with Hot Tub
Chalet · 2 Guests · 1 Bedroom
$550 /night*
Fireplace
9.6 (74 reviews)
Log Cabin home with Mt Ascutney views and pool table
Cabin · 2 Guests · 1 Bedroom
$367 /night*
Fireplace
Inviting Vermont Cabin On Mount Ascutney!
Cottage · 2 Guests · 1 Bedroom
$431 /night
What Are The Most Popular Amenities in Windsor County, VT?
Top Rental Amenities in Windsor County, VT
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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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Which Accommodations Should I Pick in Windsor County, VT?
Best Accommodation Types in Windsor County, VT
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How Many Accommodations Are Pets Allowed in Windsor County, VT?
Percentage of Pet Friendly Rental Properties in Windsor County, VT
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Where Should We Visit in Windsor County, VT Area?
Points of Interests In Windsor County, VT
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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
Full Kitchen
Viewmont Chalet
Holiday home · 2 Guests · 1 Bedroom
$716 /night
Full Kitchen
10 (30 reviews)
Reading Farms Estate
Holiday home · 2 Guests · 1 Bedroom
$4,625 /night*
Full Kitchen
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*
Airbnb, Vacation House with Hot Tub in Windsor County, VT
* 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.