Vacation rentals in Windsor County

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Top-rated vacation rentals in Windsor County

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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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SUPERHOST

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