Condo vacation rentals in Windsor County
Find and book unique condos on Airbnb
Top-rated condo rentals in Windsor County
Guests agree: these condos are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Windsor County condo rentals
Weekly condo rentals
Condo in Killington
4.98 out of 5 average rating, 41 reviewsLuxury Ski Condo - with Garage Parking and Pool
Condo in Ludlow
5 out of 5 average rating, 24 reviews2 BR/2BA Ski In/Ski Out Condo on Okemo- Sleeps 6
Condo in Ludlow
5 out of 5 average rating, 17 reviewsSki Haven: 1-Bed Ski-in/out Condo, Okemo Base Area
Condo in Killington
4.95 out of 5 average rating, 98 reviews⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace
Condo in Killington
4.95 out of 5 average rating, 56 reviewsBright & Cozy ski in condo with fireplace & views
Condo in Killington
4.85 out of 5 average rating, 82 reviews1 BR Best Location w/ Pools/Massage Chair/Hottub!
Condo in Killington
4.86 out of 5 average rating, 7 reviewsKillington Renovated Studio Condo w/ Kitchenette
Condo in Rutland
5 out of 5 average rating, 20 reviewsLuxury, downtown apt w/ balcony
Pet-friendly condo rentals
Condo in Bridgewater
4.95 out of 5 average rating, 21 reviewsYear-round Fun in VT: Wonderful Country Apartment
Condo in Hartford
4.83 out of 5 average rating, 6 reviews2bd/2.5ba end-unit condo in the heart of Quechee
Condo in Bridgewater
5 out of 5 average rating, 37 reviewsFarmhouse Beauty Minutes to Woodstock & Skiing
Condo in Hanover
4.89 out of 5 average rating, 73 reviewsWalk to town - 2 bedroom condo
Condo in Killington
4.98 out of 5 average rating, 42 reviewsFun 2 BR | 2 BA Condo - Pool/Spa - Walk to Lift
Condo in Killington
4.98 out of 5 average rating, 57 reviewsDog/Family Friendly Getaway with Pool & Hot Tub
Condo in Killington
4.98 out of 5 average rating, 137 reviews2 Bedroom Condo with Loft & POOL @ The Woods
Condo in Ludlow
4.88 out of 5 average rating, 40 reviewsUnbeatable Location Ski In/Out Okemo Mt. 4 bdrm
Condo rentals with a pool
Condo in Killington
4.93 out of 5 average rating, 88 reviewsCozy 1-bed, Mountain Green Resort - Killington, VT
Condo in Killington
4.9 out of 5 average rating, 10 reviewsNorthlands at Trail Creek
Condo in Killington
4.95 out of 5 average rating, 60 reviews2 BED BEST Rates $ Book Now 2 min to Mtn & Apres
Condo in Quechee
4.9 out of 5 average rating, 87 reviewsCondo on Quechee Golf Course with Private Feel
Condo in Killington
4.89 out of 5 average rating, 74 reviewsLuxe Trailside Ski On/Off. Next to hot tub
Condo in Ludlow
5 out of 5 average rating, 19 reviewsJackson Gore/Okemo Ski-in/Out Slopeside Studio
Condo in Killington
4.89 out of 5 average rating, 61 reviews1BR Ski-Home Pool/HotTb, Walk 2 Lifts, golf
Condo in Killington
4.96 out of 5 average rating, 45 reviewsWalk to lift, Ski home, Sunny with loft
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