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
4.88 out of 5 average rating, 51 reviewsKillington Ski Condo: Your Winter Escape!
Home in Mendon
4.88 out of 5 average rating, 230 reviewsRanch at Mendon Mt Orchards
Home in Hartford
5 out of 5 average rating, 23 reviewsLuxury Home w/ Hot Tub - close to Quechee Club
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 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
4.88 out of 5 average rating, 32 reviewsCozy, Renovated Quechee Treehouse
Weekly house rentals
Home in Cavendish
5 out of 5 average rating, 25 reviewsVT Cabin near Okemo & Killington
Home in Woodstock
4.87 out of 5 average rating, 45 reviewsBeautiful Village of Woodstock home near the Inn
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 Hartford
4.97 out of 5 average rating, 99 reviewsLuxury Barn Home w/Hot Tub, Sauna, Gardens MtnView
Home in Sharon
4.99 out of 5 average rating, 96 reviewsThe Willow House: a Modern Vermont Retreat
Home in Woodstock
4.97 out of 5 average rating, 64 reviewsPet Friendly Woodstock Home; Minutes to Killington
Home in Woodstock
4.98 out of 5 average rating, 56 reviewsThe DeerBrook, Distinctive Vermont Lodging
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 Pittsfield
5 out of 5 average rating, 13 reviewsSkyeburst | Modern Mtn Home
Home in Andover
5 out of 5 average rating, 44 reviewsAmazing Views and Sunsets
Home in Woodstock
4.92 out of 5 average rating, 24 reviewsGrange Hall, South Woodstock Historic Home
Home in Hartford
New place to stayQuaint Quechee A-Frame
Home in Mount Holly
4.96 out of 5 average rating, 51 reviewsModern VT Farmhouse w/Hot Tub - 10 mins to Okemo
Home in Ludlow
5 out of 5 average rating, 27 reviewsAFrame w/ lake ~ 5min to Okemo ~ 15 to Killington
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