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