Condo vacation rentals in Windsor County

A cozy living space features a large window providing natural light. A comfortable couch and chair are positioned around a coffee table. The room includes a spacious bed with a blue and black patterned blanket, while a 50-inch TV is mounted on the wall.

4.88 out of 5 average rating, 265 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.

A cozy living area features a deep leather sofa positioned near a stone fireplace. A large window opens to the balcony, inviting natural light. A TV is mounted above a wooden mantle, and a small table and chair provide a space for work or dining.

4.99 out of 5 average rating, 160 reviews

Elegant Alpine Condo - Golf, Bike & Pool!

Newly renovated 1-bedroom Whiffletree condo with an upscale alpine feel—just minutes from Killington Resort, golf course and access road. Fully stocked with essentials and includes a locker for your gear. Relax and enjoy the onsite outdoor pool (Open Memorial Day - Labor Day). Easy access to summer fun and scenic Vermont trails! Sleeps up to 4 with a king bed and queen pullout sofa. Baby Pack & Play crib, mattress and sheets available upon request for $25 per stay. Killington Reg #007718

A spacious living area features comfortable seating on a plush sofa and armchairs. A round wooden coffee table is positioned centrally, alongside a dining table with multiple wooden chairs. Natural light fills the space through large windows, enhancing the cozy atmosphere.

4.82 out of 5 average rating, 172 reviews

Free Shuttle Route-Charming 3 BR 2 BA Ski Home/Off

Looking to enjoy all that Killington has to offer in just minutes? Ski home access, a prime location on the shuttle route, and just a 2-minute drive to the slopes. Super convenient! This newly refreshed three-bedroom, two-bathroom condo offers modern comfort and a cozy vibe. After a day of outdoor fun, kick back on the plush sofa and unwind by the warmth of the gas fireplace. It's the ultimate retreat to recharge and enjoy the beauty of Vermont. SHUTTLE OPERATES FRIDAY-SUNDAY & HOLIDAY WEEKS

A tranquil sleeping area features a cozy bed with soft bedding and accent pillows. Nightstands with lamps are placed on either side, providing gentle light. A large horse portrait adorns the wall above the bed, contributing to the serene ambiance.

4.92 out of 5 average rating, 107 reviews

Spring Great Deal Cozy 2 Bedroom .2 mi to lift

Come enjoy this peaceful retreat, a warm fire and ski-in trail (depends on snowfall) with beautiful Mountain views! Our cozy 2 bedroom 1 bath is nestled away right on the golf course near Snowshed; Minutes away from ski lifts, restaurants and night life. Enjoy a warm space by the fire after skiing, snowmobiling, tubing and shopping! Shuttle every 30 min weekend & holiday weeks- Common laundry room -free washer/dryer Ski Locker- Pool heated in the summer Enjoy the Beast of the East!

4.94 out of 5 average rating, 105 reviews

A living area features a gray sofa adorned with decorative pillows in various patterns. A wooden coffee table sits in front, and a side table with a lamp complements the space. Light filters through a sliding glass door, which opens to a patio.

Condo in Ludlow

Ground Floor, Okemo True Ski-in/Ski-Out

Put your gear on the patio and just walk out to the slopes! Okemo Mountain Lodge ground floor unit. C-building is the closest property to the A-Quad/B-Quad lift. Come enjoy convenient skiing, free parking and fast internet. Ski school gathers right outside the patio. How convenient it is to make your own meal during a powder day! Please note there is no AC at this condo complex summer time. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

A spacious living area features large windows allowing natural light to fill the room. A comfortable sectional sofa is arranged around a coffee table, and a TV is positioned near a wood-burning fireplace. A decorative artwork of a bull's head adorns the wall.

4.96 out of 5 average rating, 171 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).

A modern kitchen with a circular dining table surrounded by four wooden chairs is featured. Stainless steel appliances, including a microwave and oven, are present. A stylish light fixture hangs above the table, while the fireplace and sports equipment are visible in the background.

4.92 out of 5 average rating, 220 reviews

Cozy 1BR, Shuttle/Walk to Lifts, Covered Parking

Our bright and cozy 1-bedroom condo in Building 3 at Mountain Green Resort is the perfect home base for your Killington getaway. Reserved parking spot in the garage. Walk to Snowshed Base Lodge or hop on the winter shuttle that runs every 15 minutes. Enjoy a renovated kitchen, dedicated Wi-Fi, and smart TVs for easy streaming. Resort amenities include an indoor pool, hot tub, sauna, and gym year-round, plus an outdoor pool from Memorial Day through mid-September.

A spacious living room features a real wood fireplace with a modern hearth, surrounded by a cozy seating arrangement. A flat-screen television is mounted above the fireplace. Large windows provide natural light and a view of the outdoor balcony, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 110 reviews

⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed

Ski On-Ski Off cozy mountain condo with Real Wood Fire Place and King Size Bed in Sunrise Village on Killington Mountain. Updates include all new furniture in the Master Bedroom & Guest Bedroom, all new top of the line Stainless Steel Appliances in the gourmet kitchen, Tastefully decorated Living Room with new queen size sleep sofa & matching chairs. Simply walk to the end of the parking lot to the Ski On/Off trail. I own the adjoining unit -more info below.

4.95 out of 5 average rating, 189 reviews

A cozy living room features warm wooden paneling and a plush sofa facing a mounted flat-screen television. A circular coffee table sits in the center, complemented by a floor lamp and a side chair. A fireplace adds a comforting touch, creating a welcoming space.

Condo in Ludlow

Lovely 1-Bedroom condo with indoor fireplace!

This cozy condo is exactly what a close group of 4-5 people need for a wonderful ski experience. Located centrally in the beautiful town of Ludlow this location is close to everything you could want. It sits on the bus route for Okemo Mountain, and is walkable to groceries, restaurants and bars. "Eight Oh Brew" tap house is located on the base floor of the building. This location has free onsite parking, free firewood and coin laundry machines.

A spacious living area features a plush sofa, a wooden dining table with chairs, and a large window allowing natural light. An electric fireplace is positioned against a stone wall, and a smart TV is mounted above a media console. The decor includes subtle rustic elements.

4.95 out of 5 average rating, 168 reviews

Spring Deals • Quiet Dog-Friendly Mountain Escape

🌸 Spring deals now available — enjoy one of the best values in Killington this season Escape to a quiet, dog-friendly mountain retreat surrounded by nature. Close to hiking trails and outdoor adventures, this cozy condo features an electric fireplace, Xbox, arcade game, cable TV, and fast Wi-Fi for a fun and relaxing stay. While on-site amenities are temporarily closed for maintenance, alternate access is available upon request.

A cozy living area is furnished with a grey sofa and two patterned chairs. A wooden coffee table sits center stage, complemented by a stone fireplace. A large television is positioned on a wooden media console, while sliding glass doors offer access to an outdoor balcony, revealing greenery.

4.94 out of 5 average rating, 231 reviews

Newly renovated ski retreat at Killington

Located at Mountain Green Resort, Building III. Walk to Snowshed Lodge to begin your day of skiing, or take the free shuttle that will pick you up outside the entrance. After your day of skiing ends and you return to the unit, to experience the many amenities that the resort has to offer: indoor pool, eucalyptus steam room, two spas, sauna, fitness center,. You may prefer to stay in the unit and watch skiers come down the mountain.

Superhost

Aerial view of the Mtn Green Resort complex, surrounded by a blanket of fresh snow. The snow-covered mountains in the background and the tree-lined foreground offer a serene winter landscape. Several condo buildings are visible, showcasing multiple stories and a mix of windows.