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
Get the amount of space that is right for you
Popular amenities for Windsor County condo rentals
Weekly condo rentals
Condo in Killington
4.9 out of 5 average rating, 119 reviewsCozy & Convenient Ski Home Condo
Condo in Plymouth
4.89 out of 5 average rating, 123 reviewsCanyons Unit: 2mi to Killington’s Skyeship Gondola
Condo in Killington
4.94 out of 5 average rating, 178 reviewsWalk or Shuttle to Lifts/2BR @ Mt. Green Resort
Condo in Ludlow
4.95 out of 5 average rating, 167 reviewsExceptional Village Fireplace Condo On Shuttle Rte
Condo in Killington
4.82 out of 5 average rating, 250 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Condo in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
Condo in Mendon
4.88 out of 5 average rating, 100 reviews105 Fox Hollow Village Pvt - Red Fox - Unit B-4
Condo in Killington
5.0 out of 5 average rating, 37 reviewsEntire Condominium for your base camp
Pet-friendly condo rentals
Condo in Ludlow
4.95 out of 5 average rating, 115 reviewsRustic Condo-Long Term Summer Rental Available
Condo in Hartford
4.76 out of 5 average rating, 128 reviewsSecluded cabin. Quechee, VT 17 min to Dartmouth
Condo in Bridgewater
4.93 out of 5 average rating, 15 reviewsYear-round Fun in VT: Wonderful Country Apartment
Condo in Ludlow
4.95 out of 5 average rating, 59 reviewsOkemo’s Back Room -Heart of the village on shuttle
Condo in Ludlow
4.89 out of 5 average rating, 36 reviewsModern Okemo condo! Walk to town, 1/2mi to lifts
Condo in Bridgewater
5.0 out of 5 average rating, 31 reviewsFarmhouse Beauty - River, Woodstock, & Killington
Condo in Killington
4.96 out of 5 average rating, 71 reviewsCozy Mountainside condo - Dogs Welcome!
Condo in Killington
4.97 out of 5 average rating, 36 reviewsFun 2 BR | 2 BA Condo - Spa - Walk/Shuttle to Lift
Condo rentals with a pool
Condo in Killington
4.93 out of 5 average rating, 107 reviewsLocation! Cozy 2BR Condo - Mountain Side
Condo in Ludlow
4.8 out of 5 average rating, 149 reviewsEnjoy a Ski-On/Ski-Off Okemo Ski Getaway
Condo in Killington
4.83 out of 5 average rating, 121 reviewsCharming 3 Bedroom 2 Bath Ski Home/Off
Condo in Killington
4.86 out of 5 average rating, 107 reviewsSummer rental - Near Resort 4 Bedroom - Pool
Condo in Killington
4.78 out of 5 average rating, 163 reviewsAmazing,Ski, Golf, Hike, Bike, Adventures
Condo in Cavendish
4.79 out of 5 average rating, 47 reviewsHotel Standard Condo Minutes from Okemo
Condo in Killington
4.83 out of 5 average rating, 65 reviewsSnowshed, Ramshead Ski Lodges in walking distance!
Condo in Killington
4.79 out of 5 average rating, 70 reviews3BR Condo Minutes from the Slopes!
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