Condo vacation rentals in Windsor County

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Top-rated condo rentals in Windsor County

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Guest favourite

Condo in Killington

4.91 out of 5 average rating, 194 reviews

Ski in/out newly renovated 1brm condo at Pico base

Newly renovated 1 bedroom condo with slope side Mountain view that is seconds away from the lodge and lift.Balcony facing lodge and slopes, 50”flatscreen TV, WiFi,fireplace, new carpet, new queen size mattress/box spring ,custom black walnut headboard and night stands.New queen size sofa bed. Renovated bathroom and new granite kitchen countertops w/new stools.Newer appliances and refurbished cabinets. Fully equip kitchen, free ski locker and firewood. Coin Op laundry.Free bus to Killington base.

Guest favourite

Condo in Plymouth

4.9 out of 5 average rating, 131 reviews

Canyons Unit: Hot Tub, 2mi to Skyeship Gondola

The Canyons Unit is a freshly renovated, fully separate, ground level, 2 bedroom apartment in our four-family French Chalet. We are 1 mile to lakes and summer camps and 2 miles from Killington’s Skyeship Gondola. It is 15 minutes from Killington’s main base area and 20 minutes to Okemo. If this listing isn’t available for your interested vacation dates, check out our sister listing called the Moguls Unit. We also have larger 4 bedroom units (The Ledges and Glades) at this same location too.

Guest favourite

Condo in Killington

4.92 out of 5 average rating, 154 reviews

Renovated 1BR, Walk to Lifts, Covered parking

Our comfortable 1-bedroom condo in Building 3 of the Mountain Green Resort provides a bright yet cozy home base for your Killington getaway. Our condo features a new kitchen, dedicated Wi-Fi, and smart TVs. Conveniently located within walking distance to Snowshead, it's perfect for all your mountain activities. Please note, construction teams are replacing the roof of each bldg 7am-7pm daily through the 1st week of November. Scaffolding is up around the outside and the balcony is unavailable.

Guest favourite

Condo in Ludlow

4.92 out of 5 average rating, 130 reviews

All Season Lovely and Zen Okemo Mt Lodge Condo

Tired of city life and want a fresh breath? Feel the call from nature while also desiring some sporty fun? Come enjoy our lovely and Zen Condo right at the foot of beautiful Okemo! True ski-in/ski-out in the winter. Enjoy your warm ski day lunch by sitting next to the wood-burning fireplace*, while watching all the activities on the slope. In the warm weather, enjoy the beautiful hiking trails and golf course that Okemo offers, as well as water activities at the nearby lakes and rivers.

Guest favourite

Condo in Killington

4.95 out of 5 average rating, 196 reviews

Bike to Lifts/2BR @ Mt. Green Resort next to Golf!

Our CLEAN & SPACIOUS 2 Bedroom and 1.5 Bath Condo is a corner unit in the 4 Season Mountain Green Resort which is located directly across the street from the Snowshed Base Lodge at Killington Mountain (just a 10 minute walk or 2 minute shuttle ride to the slopes) and right next door to the Killington Golf Course. With our recently updated kitchen, renovated master bathroom, luxury vinyl flooring and new furniture, you are sure to enjoy our home away from home in the Green Mountains!

Guest favourite

Condo in Killington

4.93 out of 5 average rating, 125 reviews

CozyCub Shuttle on/ski home, Fireplace, Walk out

Delight in this friendly, fully renovated (2022) modern ski condo next to Killington's popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65" TV. Enjoy the Whiffletree condo association's outdoor pool and tennis courts in the summer, settle in by the gas fireplace, or head out to explore.

Guest favourite

Condo in Killington

4.95 out of 5 average rating, 150 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

<b>Seeking Adventure?</b> This end unit garden level condo is minutes to Killington AND Pico! Easy access to the Appalachian Trail to ATV, mountain bike, hike, and swim. <b>Relaxing?</b> Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to VT nonprofits.

Guest favourite

Condo in Killington

4.96 out of 5 average rating, 125 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

Contactless checkin steps from Killington Skiing/ Mountain Biking/ Adventure Center, refurbished ski-home condo with its own private sauna, hotel-style condo amenities, excellent common area (pool, jacuzzi, showers, etc) in idyllic central Vermont. Travel guide provided after booking! The resort includes an indoor pool, two hot tubs, pool table, treadmills, and is nestled at the base of the mountain with its own ski-home trail (or mountain bike-home in the summer).

Guest favourite

Condo in Ludlow

4.91 out of 5 average rating, 125 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

Guest favourite

Condo in Killington

4.93 out of 5 average rating, 149 reviews

Renovated unit, prime location! Shuttle on/Ski off

We are located in Killington, VT. A newly renovated family friendly condo complex located on East Mountain Rd. Take the free shuttle (modified schedule post Covid) and end your day by skiing back to the condo. In the summer season you can enjoy a day mountain biking and ride home in just under five minutes. Enjoy the outdoor pool during the summer after a day of mountain biking! Year round activities all within a short distance.

Superhost

Condo in Killington

4.82 out of 5 average rating, 153 reviews

Skier's Retreat 2bed/1.5 bath condo w/ Amenities

Welcome to the heart of Killington, a 4 season Resort Style condo with free shuttle and walkabilty to Snowshed lodge. This 900 sqft 2 bedroom, 1.5 Bathroom has everything you could need to relax after a long day on the mountain. Come soak in the hot tub or indoor pool and sauna. Outdoor locker for ski gear and free parking. Updated kitchen and private patio overlooking the back of the golf course. Hope to see you soon!

Guest favourite

Condo in Killington

4.93 out of 5 average rating, 228 reviews

Dogs Welcome! - Spa Onsite w/Pool, Hot Tub 2BD/2BA

This 2 bed, 2 bath home in Killington is located in The Woods, a luxury condo complex. It features a spacious living room, fully equipped kitchen, and wood-burning fireplace. Guests have access to amenities like an indoor pool, hot tub, steam room and spa. The home is also dog-friendly with lots of open space to walk your furry friend. Perfect for a comfortable and enjoyable getaway in Killington!