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Vacation Homes in Windsor County
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Our top choices for Windsor County vacation homes
1. Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to WoodstockHartford
10.0 out of 10, Exceptional, (167 reviews)
"Wonderful place."
Marty O.
2. Bright, Family-Friendly Lake View House Close to Okemo, Killington, Pico, Lakes
Bright, Family-Friendly Lake View House Close to Okemo, Killington, Pico, LakesPlymouth
9.8 out of 10, Exceptional, (46 reviews)
"A great stay and the house met expectations. We enjoyed our stay in the area. "
Karl R.
3. The Dorothy-10 minutes from Okemo- freshly renovated
The Dorothy-10 minutes from Okemo- freshly renovatedCavendish
9.6 out of 10, Exceptional, (8 reviews)
"Charming place – – wonderful, responsive hosts. "
Richard P.
4. Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayakBarnard
9.8 out of 10, Exceptional, (82 reviews)
"Classic Vermont property and setting. "
Josh A.
5. Birch Lodge - mountain views, hottub, minutes to Okemo!
Birch Lodge - mountain views, hottub, minutes to Okemo!Ludlow
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful stay everything you need Thanks so much"
Maureen b.
6. PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.Woodstock
9.8 out of 10, Exceptional, (242 reviews)
"Great spot, in a lovely location! "
Beth W.
7. Quechee - Four Season Resort Townhome and access to The Quechee Club
Quechee - Four Season Resort Townhome and access to The Quechee ClubQuechee
9.8 out of 10, Exceptional, (20 reviews)
"We loved our time here. The condo was very clean and everything was as shown and described in the listing. Paige was very communicative with our questions and made checkin/checkout very easy. Loved our time here and in Quechee. We will definitely come back!"
Greg S.
8. SALE! MUSIC on the Mountain! Come enjoy this cozy, renovated home by Okemo Mtn!
SALE! MUSIC on the Mountain! Come enjoy this cozy, renovated home by Okemo Mtn!Ludlow
10.0 out of 10, Exceptional, (35 reviews)
"Perfect for our family. Easy access and everything we needed."
Ryan W.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor County Hotel Reviews
Jackson Gore Village, A Vail Resorts Property
8/10 Good
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