
House holiday rentals in Windsor County
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Top-rated house rentals in Windsor County
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Windsor County
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Pond, Pool, Mountain Views | Au Bout du Chemin

Ranch at Mendon Mt Orchards

Walk to Okemo Ski Lift - Private Classic VT Ski Ch

Dana Road House Sunlit VT Country Home w/HotTub

Bright & Modern Quechee Town House - Self Check-In

Private Farmhouse with in ground pool!

Comfortable, relaxing large country home
Weekly house rentals

Ludlow Lake & Ski Cottage - Adventure Awaits!

New Listing! Close to Woodstock, Country Setting

Cornish-Windsor Bridge Retreat with Amazing Views

Quechee Vermont Home

Cheerful, Restored 1940s Cape- 5 mins to Woodstock

Hiker’s Hygge on 21 Acres and Aqueduct Trails

Stunning 3 br Timber Frame ski retreat on 6 Acres

OQ Farm Refectory House with Fire Place and Sauna
Private house rentals

19th Century Bohemian Barn House

BEST Views! Close to Silver Lake + Woodstock VT

Beautiful Village of Woodstock home near the Inn

Tranquility Farm 3

The Cornish Cottage

Renovated Farmhouse: serene, modern & private

Riverside Home Woodstock VT

The Barn at Cold River ~ 20 minutes to Ski Resorts
Destinations to explore
- Rentals with a firepit Windsor County
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- Rentals with a sauna Windsor County
- Fitness-friendly rentals Windsor County
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- Bed and breakfasts Windsor County
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- Farm stay rentals Windsor County
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- Rentals with a fireplace Windsor County
- Rentals with pools Windsor County
- Family-friendly rentals Windsor County
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pats Peak Ski Area
- Fort Ticonderoga
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Dorset Field Club
- Tenney Mountain Resort
- Stratton Mountain Resort
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Bretwood Golf Course
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Baker Hill Golf Club
- Mount Sunapee Resort
- Veterans Memorial Recreation Area Ski Hill
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Crotched Mountain Ski and Ride
- Things to do Windsor County
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