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 Mendon
4.88 out of 5 average rating, 229 reviewsRanch at Mendon Mt Orchards
Home in Killington
4.98 out of 5 average rating, 120 reviewsSugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace
Home in Woodstock
4.96 out of 5 average rating, 57 reviewsDana Road House Sunlit VT Country Home w/HotTub
Home in Hartford
4.94 out of 5 average rating, 18 reviews4 bedroom Farmhouse w/ Peloton & spacious yard
Home in Plainfield
4.89 out of 5 average rating, 136 reviewsHistoric Home on 17 acres of land. Go escape!
Home in Hartford
4.88 out of 5 average rating, 32 reviewsCozy, Renovated Quechee Treehouse
Home in Hartford
4.87 out of 5 average rating, 15 reviewsElegance Meets Rustic Charm: Vermont 3-Bed Retreat
Weekly house rentals
Home in Pittsfield
5 out of 5 average rating, 13 reviewsSkyeburst | Modern Mtn Home
Home in Cavendish
5 out of 5 average rating, 25 reviewsVT Cabin near Okemo & Killington
Home in Hartford
4.85 out of 5 average rating, 53 reviewsQuechee Vermont Home
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 Windsor
4.99 out of 5 average rating, 72 reviewsMountainside cabin close to everything, with views
Home in Cavendish
4.95 out of 5 average rating, 19 reviewsCharming 3BR 1Bth New England Cape- Experience VT!
Home in Bridgewater
5 out of 5 average rating, 14 reviewsCozy 1890s farmhouse
Private house rentals
Home in Plymouth
4.95 out of 5 average rating, 43 reviewsKillington - Woodstock: Private Oasis w/ Hot-Tub
Home in Barnard
4.99 out of 5 average rating, 88 reviewsBEST Views! Close to Silver Lake + Woodstock VT
Home in Rutland
4.95 out of 5 average rating, 19 reviewsMountain Getaway: 10 mins to Pico 20 to Killington
Home in Bridgewater
4.96 out of 5 average rating, 23 reviewsOQ Farm Refectory House with Fire Place and Sauna
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, 99 reviewsLuxury Barn Home w/Hot Tub, Sauna, Gardens MtnView
Home in Ludlow
5 out of 5 average rating, 26 reviewsAFrame w/ lake ~ 5min to Okemo ~ 15 to Killington
Home in West Windsor
5 out of 5 average rating, 77 reviews3BR Country Retreat: Close to Mt Ascutney
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