Condo vacation rentals in Windsor County
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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
4.93 out of 5 average rating, 148 reviewsRenovated, w/Covered Parking-Shuttle-Walk to Lifts
Sep 11 – 18
Condo in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
Aug 30 – Sep 6
Condo in Ludlow
4.95 out of 5 average rating, 167 reviewsExceptional Village Fireplace Condo On Shuttle Rte
Aug 5 – 12
Condo in Killington
4.93 out of 5 average rating, 107 reviewsLocation! Cozy 2BR Condo - Mountain Side
Oct 27 – Nov 3
Condo in Killington
4.83 out of 5 average rating, 120 reviewsCharming 3 Bedroom 2 Bath Ski Home/Off
Dec 2 – 9
Condo in Killington
4.82 out of 5 average rating, 250 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Apr 17 – 24
Condo in Mendon
4.88 out of 5 average rating, 100 reviews105 Fox Hollow Village Pvt - Red Fox - Unit B-4
Oct 30 – Nov 6
Condo in Killington
4.82 out of 5 average rating, 148 reviewsSkier's Retreat 2bed/1.5 bath condo w/ Amenities
Jul 23 – 30
Pet-friendly condo rentals
Condo in Ludlow
4.95 out of 5 average rating, 115 reviewsRustic Ski Condo in Historic Mill
May 19 – 26
Condo in Hartford
4.76 out of 5 average rating, 126 reviewsSecluded cabin. Quechee, VT 17 min to Dartmouth
Dec 1 – 8
Condo in Killington
4.97 out of 5 average rating, 36 reviewsFun 2 BR | 2 BA Condo - Spa - Walk/Shuttle to Lift
May 7 – 14
Condo in BRIDGEWTR COR
5.0 out of 5 average rating, 3 reviewsCharming 2BR Condo - 10 min to Skyship Gondola!
Jan 26 – Feb 2
Condo in Bridgewater
4.93 out of 5 average rating, 15 reviewsYear-round Fun in VT: Wonderful Country Apartment
Nov 3 – 10
Condo in Bridgewater
5.0 out of 5 average rating, 31 reviewsFarmhouse Beauty - River, Woodstock, & Killington
Oct 27 – Nov 3
Condo in Ludlow
4.95 out of 5 average rating, 59 reviewsOkemo’s Back Room - on the shuttle route!
Oct 26 – Nov 2
Condo in Killington
4.96 out of 5 average rating, 70 reviewsCozy Mountainside Condo Dog Allowed Sleeps 4
Aug 10 – 17
Condo rentals with a pool
Condo in Killington
4.9 out of 5 average rating, 232 reviewsA Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
Jan 1 – 8
Condo in Killington
4.78 out of 5 average rating, 163 reviewsAmazing,Ski, Golf, Hike, Bike, Adventures
Nov 27 – Dec 4
Condo in Killington
4.86 out of 5 average rating, 107 reviewsSummer rental - Near Resort 4 Bedroom - Pool
Jan 21 – 28
Condo in Killington
4.8 out of 5 average rating, 106 reviewsKillington Escape 2 Story 2BR 2BA Main Building
May 14 – 21
Condo in Killington
4.88 out of 5 average rating, 32 reviewsKillington 2Br/2Ba Ski/Golf/Bike/Hike Sleeps 6
Jun 7 – 14
Condo in Hartford
4.94 out of 5 average rating, 18 reviewsRetreat to Vermont and a lovely 2 BDRM condo
Jun 16 – 23
Condo in Killington
4.95 out of 5 average rating, 38 reviewsWalk to lift, Ski home, Sunny with loft
May 5 – 12
Condo in Killington
5.0 out of 5 average rating, 21 reviewsUpscale Condo in Heart of Killington
Sep 8 – 15
Destinations to explore
- Condo rentals Vermont
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