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Vacation rentals in Windsor County

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Top-rated vacation rentals in Windsor County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Entire cottage · Plymouth
Safe Haven! Cute Cottage in Plymouth, Vermont.
Romantic Retreat~ Rent a "room" at an inn for $260+ or rent a cottage for $250. "Like renting a whole B&B for yourself!" Private cottage for two adults. One BR & two BA. Rustic charm, modern amenities. King bed, living/dining area, full kitchen, fireplace, hot tub, porch, and fire pit. Between Killington & Okemo Mt areas 15 minutes. Woodstock 30 minutes - Ludlow 10 minutes. Overlooks Lake Amherst. Canoe Dog friendly All you need are your own clothes & food! Generous amenities.
$250 per night
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Entire rental unit · Cavendish
Murphys4Seasons Studio Proctorsville
Keep it simple at this peaceful and centrally-located place. Close to Okemo, walking distance to restaurants and brewery in the village with outdoor activities close by. Working chicken farm, we have fresh eggs and love to share. Short drive to the lakes and local swimming holes in summer. No smoking on property, no vapes, please look elsewhere if you feel the need. Kid friendly and we do have a big baby girl of a dog, she begs for pets and love, super friendly. Designated parking space on site.
$58 per night
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Private room · Cornish
Fitch Family Farm
A 225 yr old hilltop farm and house with gorgeous views, a true feeling of rural living. Newly remodeled upstairs guest bedroom with queen bed, and a full bath that is shared with the hosts. Second bedroom with double bed available for $35. Kitchen not available for cooking meals but we can accommodate small warm-ups. Pond for swimming, trails for hiking or mountain biking. No pets please. Cleaning fee included in the price. Visit our website, FitchFamilyFarm for info.
$60 per night

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Other great vacation rentals in Windsor County

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Private room · Baltimore
Wake up to Mountain views in a Vermont studio Apt.
$85 per night
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Entire rental unit · Cavendish
One Bedroom Suite Near Okemo
$113 per night
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Entire condo · Ludlow
Okemo Clock Tower Base Ski-in/Ski-out Condo
$92 per night
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Entire rental unit · Ludlow
One Bedroom Suite Near Okemo
$155 per night
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Entire guesthouse · Hartland
Cozy Guest Cabin with hot tub use and private bath
$81 per night
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Entire rental unit · Ludlow
Law Office Apartment
$100 per night
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Entire loft · Claremont
Beautiful 1 bedroom apartment with balcony
$91 per night
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Entire rental unit · Andover
Private Hilltop farm apartment
$105 per night
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Entire condo · Ludlow
Updated Condo in Downtown Ludlow
$109 per night
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Entire condo · Ludlow
Updated Two Bedroom Condo in Heart of Ludlow
$137 per night
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Entire rental unit · Hartland
Sunny Studio Apartment in Hartland
$120 per night
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Private room · Tunbridge
Mountain view
$35 per night
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