House vacation 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.
Vacation rentals for every style
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Popular amenities for Windsor County house rentals
House rentals with a pool
Home in Killington
4.9 out of 5 average rating, 184 reviewsLuxury Condo Tucked in the Heart of Killington
Home in Killington
4.9 out of 5 average rating, 49 reviewsKillington Ski Condo: Your Winter Escape!
Home in Mendon
4.88 out of 5 average rating, 228 reviewsRanch at Mendon Mt Orchards
Home in Killington
4.98 out of 5 average rating, 118 reviewsSugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace
Home in Woodstock
4.96 out of 5 average rating, 56 reviewsDana Road House Sunlit VT Country Home w/HotTub
Home in Plainfield
4.89 out of 5 average rating, 136 reviewsHistoric Home on 17 acres of land. Go escape!
Home in Bridgewater
4.89 out of 5 average rating, 46 reviewsLuxurious family retreat home in the mountains
Home in Hartford
4.9 out of 5 average rating, 31 reviewsCozy, Renovated Quechee Treehouse
Weekly house rentals
Home in Plymouth
4.95 out of 5 average rating, 43 reviewsKillington - Woodstock: Private Oasis w/ Hot-Tub
Home in Cavendish
5 out of 5 average rating, 24 reviewsVT Cabin near Okemo & Killington
Home in Pomfret
5 out of 5 average rating, 44 reviewsCheerful, Restored 1940s Cape- 5 mins to Woodstock
Home in Ludlow
5 out of 5 average rating, 89 reviewsStunning Views of Okemo - 3 Bedrooms, 3 Bath Home
Home in Bridgewater
5 out of 5 average rating, 48 reviewsHot Tub w/views! Minutes to the Mountain!
Home in Bridgewater
5 out of 5 average rating, 14 reviewsCozy 1890s farmhouse
Home in Ludlow
5 out of 5 average rating, 25 reviewsAFrame w/ lake ~ 5min to Okemo ~ 15 to Killington
Home in Woodstock
4.97 out of 5 average rating, 63 reviewsPet Friendly Woodstock Home; Minutes to Killington
Private house rentals
Home in Barnard
4.99 out of 5 average rating, 86 reviewsBEST Views! Close to Silver Lake + Woodstock VT
Home in Woodstock
4.86 out of 5 average rating, 44 reviewsBeautiful Village of Woodstock home near the Inn
Home in Woodstock
4.84 out of 5 average rating, 79 reviewsRiverside Home Woodstock VT
Home in Hartford
4.97 out of 5 average rating, 98 reviewsLuxury Barn Home w/Hot Tub, Sauna, Gardens MtnView
Home in West Windsor
5 out of 5 average rating, 76 reviews3BR Country Retreat: Close to Mt Ascutney
Home in Plymouth
5 out of 5 average rating, 7 reviewsCamp Amherst Ski and Lakeside Retreat
Home in Rutland
4.95 out of 5 average rating, 60 reviewsCheerful home near Killington, Okemo, Pico, trails
Home in Woodstock
5 out of 5 average rating, 28 reviewsWoodstock Village Retreat
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