Condo vacation rentals in Windsor County

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Top-rated condo rentals in Windsor County

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Guest favorite

Condo in Killington

4.89 out of 5 average rating, 205 reviews

Killington-Pico ski in/out Studio at base of Pico

At the base of Pico and 10 minutes from Killington. Free shuttle service from my place to Killington. I have a free ski locker and free wood for the fireplace. There is a laundry room with coin operated machines. There is a brand new 50” flat screen tv with cable. It’s a smart tv, that’s hooked up to WiFi, so you can use your Netflix, Amazon or Hulu account if you want. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for 1 day. No daily cleaning service. No parties.

May 14 – 21

R1,891 ZAR per night

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 131 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? 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 local VT nonprofits

Sep 18 – 25

R1,893 ZAR per night

Superhost

Condo in Ludlow

4.92 out of 5 average rating, 123 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.

May 10 – 17

R1,775 ZAR per night

Guest favorite

Condo in Killington

4.94 out of 5 average rating, 176 reviews

Walk or Shuttle to Lifts/2BR @ Mt. Green Resort

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!

Aug 16 – 23

R2,758 ZAR per night

Guest favorite

Condo in Killington

4.83 out of 5 average rating, 121 reviews

Charming 3 Bedroom 2 Bath Ski Home/Off

Looking to access everything Killington has to offer within 2 minutes? This is your spot! Ski off access, right on the bus route, a 2 minute drive to the mountain. Whether you're skiing, hiking, biking, shopping, or eating and drinking, you will love the convenient location to everything that is Killington. This three bedroom, two bathroom condo was just updated with a fresh look and is ready for you to come relax on the sofa in front of the gas fireplace after a long day with nature.

Oct 27 – Nov 3

R3,124 ZAR per night

Guest favorite

Condo in Bridgewater

4.89 out of 5 average rating, 113 reviews

Southgate Healing

The completely furnished apartment is newly renovated with granit countertops, new appliances, new TV and fully furnished kitchen ..It has a clawfoot bathing tub.A large deck has a lovely view. It is .7 miles to the Bridgewater Country store for essentials and the Long Trail Brewery for lunch. I am 15 minutes from both Killington and Woodstock. The internet is fiberoptic cable 5g service with cable tv. No pets .I live upstairs so quiet please after 10. No smoking.No guns or glitter.

Oct 30 – Nov 6

R2,859 ZAR per night

Guest favorite

Condo in Killington

4.96 out of 5 average rating, 103 reviews

CozyCub Pets, AC, Bike to Mtn, 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.

Oct 30 – Nov 6

R4,466 ZAR per night

Guest favorite

Condo in Killington

4.81 out of 5 average rating, 140 reviews

1BR Modern Condo @ Whiffletree Ground Fl Walkout

PRIME BASE AREA LOCATION THE HOME → King Beautyrest mattress → Coffee/Tea/Cocoa Bar → Nintendo Wii + Games → Fully Equipped & Stainless Kitchen → Fast Wifi SKI IN / SHUTTLE OUT (2022: Winter Only; Weekends only) → Shuttle to Snowshed/K1 → Ski home on a gorgeous quiet ski home trail OFF SEASON → World Class hiking & biking on Killington Mountain OFF THE MOUNTAIN → Breweries → Antique Malls → Golf Courses → Quechee Gorge → Disk Golf → Llamas Petting

Oct 8 – 15

R3,592 ZAR per night

Guest favorite

Condo in Killington

4.87 out of 5 average rating, 149 reviews

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

This rustic Mountain Green Resort condo offers easy access to ski/mtn bike lifts with resort style amenities. Features include 4K Smart TVs, High speed WiFi, private balcony with mountain views, board games, and full kitchen. On-site health spa including pool, sauna, hot tub, gym, masseuse. Restaurants and nightlife are minutes down the road. Restaurant/bar and ski/rental shop also within resort. Free shuttle to lifts available during ski season.

May 19 – 26

R2,386 ZAR per night

Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 123 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.

Jun 16 – 23

R1,914 ZAR per night

Guest favorite

Condo in Killington

4.93 out of 5 average rating, 138 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.

Oct 17 – 24

R2,455 ZAR per night

Superhost

Condo in Killington

4.82 out of 5 average rating, 148 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 or walkable 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!

Jun 6 – 13

R2,527 ZAR per night