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 Plainfield
4.89 out of 5 average rating, 119 reviewsHistoric Home on 17 acres of land. Go escape!
Home in Woodstock
4.98 out of 5 average rating, 52 reviewsDana Road House Sunlit VT Country Home w/HotTub
Home in Hartford
5.0 out of 5 average rating, 20 reviewsCozy, Renovated Quechee Treehouse
Home in Killington
5.0 out of 5 average rating, 31 reviewsBearmont! Pool, HotTub, AC, FirePit
Home in Killington
5.0 out of 5 average rating, 29 reviews* Slope Side Sauna w/ Shuttle *
Home in Bridgewater
4.9 out of 5 average rating, 41 reviewsLuxurious family retreat home in the mountains
Home in Killington
4.98 out of 5 average rating, 46 reviewsGlamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
Home in Springfield
4.93 out of 5 average rating, 87 reviewsSki Mountain View Estate
Weekly house rentals
Home in West Windsor
4.98 out of 5 average rating, 127 reviewsFirewheel Hill: Private, contemporary house
Home in South Londonderry
4.85 out of 5 average rating, 101 reviewsLovers Honey Pond Treehouse with hot tub & sauna
Home in Rochester
4.98 out of 5 average rating, 124 reviewsModern Farmhouse on 25 Acres - Superb Views
Home in Reading
4.87 out of 5 average rating, 117 reviewsGreystone 1830
Home in West Windsor
4.97 out of 5 average rating, 58 reviewsBirdie's Nest Guesthouse
Home in Barnard
4.98 out of 5 average rating, 90 reviewsThe Looking Glass, a modernistic escape
Home in Cornish
4.95 out of 5 average rating, 19 reviewsDreamy Nature & Art Farm near Dartmouth, KUA, DHMC
Home in Hartland
4.95 out of 5 average rating, 39 reviewsCozy 1 bedroom home with private hot tub
Private house rentals
Home in Thetford
5.0 out of 5 average rating, 28 reviewsPop's Lodge
Home in Windsor
5.0 out of 5 average rating, 54 reviewsModern custom home on a side of Mt Ascutney
Home in South Woodstock
5.0 out of 5 average rating, 75 reviewsQuintessential Vermont 1820s 4-Bd Stone Farm House
Home in Cavendish
5.0 out of 5 average rating, 99 reviewsMidcentury Hillside Retreat - Summer Paradise
Home in Hancock
4.91 out of 5 average rating, 89 reviewsThe Branch House | between Sugarbush & Killington
Home in Hancock
4.96 out of 5 average rating, 47 reviewsShimla - A Mountain Retreat
Home in West Windsor
5.0 out of 5 average rating, 56 reviews3BR Country Retreat: Close to Mt Ascutney
Home in Woodstock
4.84 out of 5 average rating, 74 reviewsRiverside Home Woodstock VT
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