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!
Jan 1 – 8
Home in Killington
4.98 out of 5 average rating, 46 reviewsGlamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
May 10 – 17
Home in Woodstock
4.98 out of 5 average rating, 52 reviewsDana Road House Sunlit VT Country Home w/HotTub
Apr 27 – May 4
Home in Hartford
5.0 out of 5 average rating, 20 reviewsCozy, Renovated Quechee Treehouse
Feb 10 – 17
Home in Bridgewater
4.9 out of 5 average rating, 41 reviewsLuxurious family retreat home in the mountains
Dec 29 – Jan 5
Home in Killington
5.0 out of 5 average rating, 29 reviews* Slope Side Sauna w/ Shuttle *
Sep 18 – 25
Home in Hartford
4.95 out of 5 average rating, 19 reviewsNew! Top of the Hill - 3 bd/2.5ba home!
Nov 7 – 14
Home in Hartford
5.0 out of 5 average rating, 35 reviewsLuxury Lodge Oasis Near Dartmouth and Ski Resorts
Oct 26 – Nov 2
Weekly house rentals
Home in West Windsor
4.98 out of 5 average rating, 127 reviewsFirewheel Hill: Private, contemporary house
Sep 10 – 17
Home in Rutland
4.83 out of 5 average rating, 145 reviewsThe Green Mountain Getaway
Jun 16 – 23
Home in South Londonderry
4.85 out of 5 average rating, 101 reviewsLovers Honey Pond Treehouse with hot tub & sauna
Aug 29 – Sep 5
Home in Rochester
4.98 out of 5 average rating, 124 reviewsModern Farmhouse on 25 Acres - Superb Views
Dec 5 – 12
Home in Reading
4.87 out of 5 average rating, 117 reviewsGreystone 1830
Sep 9 – 16
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
Jul 30 – Aug 6
Home in West Windsor
4.96 out of 5 average rating, 56 reviewsBirdie's Nest Guesthouse
Jan 12 – 19
Home in Cornish
4.95 out of 5 average rating, 19 reviewsDreamy Nature & Art Farm near Dartmouth, KUA, DHMC
May 16 – 23
Private house rentals
Home in Woodstock
4.98 out of 5 average rating, 45 reviewsPet Friendly Woodstock Home; Riverside Getaway!
Oct 13 – 20
Home in Pomfret
5.0 out of 5 average rating, 42 reviewsPrivate Vermont Oasis Under 10 Mins from Woodstock
Nov 27 – Dec 4
Home in Chester
5.0 out of 5 average rating, 16 reviewsCozy 1850 farmhouse in Stone Village of Chester
Feb 22 – Mar 1
Home in South Woodstock
5.0 out of 5 average rating, 75 reviewsQuintessential Vermont 1820s 4-Bd Stone Farm House
May 10 – 17
Home in Windsor
5.0 out of 5 average rating, 54 reviewsModern custom home on a side of Mt Ascutney
Jan 1 – 8
Home in Cavendish
5.0 out of 5 average rating, 99 reviewsMidcentury Hillside Retreat - Summer Paradise
Nov 11 – 18
Home in Woodstock
4.84 out of 5 average rating, 74 reviewsRiverside Home Woodstock VT
Oct 21 – 28
Home in Thetford
5.0 out of 5 average rating, 28 reviewsPop's Lodge
Oct 28 – Nov 4
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