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Condo vacation rentals in Windsor County

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Top-rated condo rentals in Windsor County

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Guest favorite
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.
Condo in Killington
4.88 out of 5 average rating, 260 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.

Top guest favorite
A living room with a gas fireplace built into a brick facade provides warmth. A comfortable sectional couch faces the fireplace, complemented by a small coffee table. Large sliding glass doors open to a balcony, offering views of greenery outside.
Condo in Killington
4.98 out of 5 average rating, 157 reviews

Cozy Mountain Condo

Updated 1 Bdr Whiffletree condo in the heart of Killington minutes from everything. The condo is fully stocked with all of the essentials you will need for your Vermont get away. Ski locker for all your gear! Sleeps up to 4 with a king bed and queen pullout sofa. Baby Pack & Play crib, mattress and sheets available upon request for $50 per stay. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). Killington Reg #004858

Top guest favorite
The living area features a cozy seating arrangement with a brown couch and recliners, complemented by a decorative area rug. A coffee table sits in front of the seating, and a dining table with wooden chairs is positioned nearby. Soft lighting enhances the welcoming ambiance.
Condo in Killington
4.94 out of 5 average rating, 285 reviews

Walk/Bike to Snowshed Lift 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!

Guest favorite
An aerial view captures the snow-covered Pico Mountain with ski trails visible on the slopes. The surrounding trees are dusted with snow. The Village Square at Pico Condo Association is seen at the base, with buildings arranged neatly alongside a parking area.
Condo in Killington
4.92 out of 5 average rating, 116 reviews

Ski-on/ski-off 3BR at base of Pico Mountain!

Ski-on/Ski-off!! Our condo is at the base of Pico Mountain and offers amazing views from the private balcony. Enjoy all the benefits of being slope side of Pico Mountain while just 10 minutes away from Killington Resort! Pico Mountain offers 57 trails with 6 lifts and is a family-favorite to avoid some of the weekend crowds at Killington. Less then 1 mile from the Long Trail and Deer Leap overlook hiking trail. Both fantastic must-do hikes when in the area!

Top guest favorite
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.
Condo in Killington
4.94 out of 5 average rating, 108 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.

Top guest favorite
A spacious living room features a comfortable sectional sofa facing a propane fireplace. A mounted TV is positioned above the hearth. Natural light enters through sliding glass doors leading to a private porch, surrounded by lush greenery.
Condo in Mendon
4.94 out of 5 average rating, 126 reviews

Hotel Chic - Home Comfort -Ski Easy.

❄️HOTEL CHIC - SKI EASY ❄️ELEGANT - COZY - SPOTLESS ❄️OUR ULTRA COZY RETREAT ❄️WAITS JUST FOR YOU ❄️PERFECT WINTER RETREAT 🏂⛷️❄️❄️❄️❄️⛷️🏂 ⛷️ 🏂Pico-5 minutes ⛷️ 🏂Killington-15 minutes ❄️❄️SUPERHOST RATED❄️❄️ ❄️Squeaky Clean ❄️Fireplace, WIFI ❄️TV in living room & bedroom ❄️Adjustable queen bed ❄️Private covered porch ❄️Keypad check in ❄️Smoke free/Pet free NOTE: Condo regs allow 2 adults(21 yrs). Can not accommodate children.

Top guest favorite
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
4.95 out of 5 average rating, 183 reviews

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.

Top guest favorite
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.
Condo in Killington
4.93 out of 5 average rating, 222 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.

Top guest favorite
A view of the snow-covered path leading to the ski slopes is framed by the C Building’s balconies. Sunlight casts long shadows across the pristine snow, highlighting the tranquil winter scene. The surrounding area is clear and inviting, with ski signage visible in the distance.
Condo in Ludlow
4.93 out of 5 average rating, 168 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 favorite
A cozy living room features a dark leather sofa adorned with decorative pillows. Above the couch, three framed nature-themed art pieces display serene mountain landscapes. A dog rests comfortably on the carpet, with soft lighting from two side lamps enhancing the peaceful ambiance.
Condo in Killington
4.95 out of 5 average rating, 164 reviews

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy gas fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!

Superhost
The living area features a spacious navy sofa adorned with colorful pillows and a light wooden coffee table. A round dining table with black chairs is present, alongside a large mirror and soft lighting that enhance the inviting space. Natural light filters through the sliding doors.
Condo in Killington
4.89 out of 5 average rating, 148 reviews

Location + Spa! - Cozy 2BR Condo - Mountain Side

Our cozy two-bedroom condo is just steps from the lifts, spa, ski shops, and restaurants, with a three-minute drive to Killington. Nestled in the Green Mountains, you’ll have access to skiing, hiking, world-class golf, snow tubing, and scenic mountain views. The condo features seasonal amenities including a pool, fitness center, hot tub, sauna, steam room, and more — perfect for both adventure and relaxation!

Top guest favorite
A cozy living room features a large gray sectional sofa and plush armchair, inviting relaxation. A wooden coffee table sits in the center, with a textured throw draped casually over it. Natural light streams through multiple windows, enhancing the welcoming ambiance of the space.
Condo in Killington
4.98 out of 5 average rating, 134 reviews

SnowCub Pets Indoor Pool Hot Tub Sauna, FirePlace

Your group will be close to everything when you stay at this centrally-located condo. Enjoy two bedrooms plus a loft for a variety of sleeping options. Condo amenities include pool, gym, spa, tennis and hot tub. You will be close to the bars, restaurants, market and coffee shops and just minutes to the Killington resort base areas.

Popular amenities for Windsor County condo rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly condo rentals

Guest favorite
A functional kitchen features wooden countertops and stainless steel appliances, including a refrigerator and stove. Soft lighting enhances the minimalist design. A dish rack is placed next to the sink, creating an organized space for food preparation.
Condo in Killington
4.85 out of 5 average rating, 47 reviews

Moonridge condo

Top guest favorite
The living room features a spacious sofa and a reclining chair, with a coffee table at the center. Natural light enters through sliding doors leading to a private deck, offering views of greenery. Two lamps provide additional lighting, complementing the soft carpeted flooring.
Condo in Ludlow
5 out of 5 average rating, 53 reviews

Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area

Superhost
Condo in Killington
4.9 out of 5 average rating, 21 reviews

Valley Park D1: Cozy Retreat Near Killington

Guest favorite
A spacious living area is highlighted by a comfortable gray sofa and a wooden coffee table. Natural light streams through large windows, complementing the warm wood paneling that separates the sleeping nook. A flat-screen TV and a cozy seating arrangement add to the inviting ambiance.
Condo in Killington
5 out of 5 average rating, 30 reviews

Cozy Slopeside Studio at Pico

Condo in Hartford
4.75 out of 5 average rating, 4 reviews

2BR condo, fireplaces, balcony, tennis, pools, w/d

Top guest favorite
A spacious living area features a large sectional sofa and cozy bean bags, complemented by a wood-burning fireplace. Natural light enters through sliding glass doors that open to a view of the outdoors. A dining table is positioned nearby, enhancing the inviting communal space.
Condo in Killington
4.9 out of 5 average rating, 60 reviews

Cozy 1BR/1BA Condo

Guest favorite
A bright living area features a spacious sectional sofa arranged around a circular wooden coffee table. A fireplace with a stone facade provides warmth, while large windows allow natural light to fill the space. Decorative art adorns the wall above the fireplace.
Condo in Hartford
5 out of 5 average rating, 21 reviews

Community Pool, Cozy Fireplace - Coach Road 7A

Guest favorite
The living room features a high wooden ceiling and a large, central fireplace. Sofas and a loveseat provide ample seating, while artwork depicting skiing is mounted above the fireplace. Windows allow natural light to enter, offering a view of the outside.
Condo in Ludlow
4.94 out of 5 average rating, 105 reviews

Okemo Ski Condo, Steps from Trails. Modern & Cozy

Pet-friendly condo rentals

Guest favorite
The living area features high wooden beam ceilings and exposed brick walls, creating a rustic ambiance. A cozy wood burning fireplace is situated beneath the wall-mounted television. Comfortable seating includes a checkered sofa and a leather chair, all complemented by a central area rug.
Condo in Ludlow
4.96 out of 5 average rating, 147 reviews

Cozy Ski Condo In Historic Mill - on shuttle route

Guest favorite
Condo in Bridgewater
4.96 out of 5 average rating, 52 reviews

Foliage and Ski Retreat by Woodstock & Killington

Guest favorite
A cast iron gas fireplace is centered on a stone hearth, providing warmth. A wooden ladder holds colorful blankets, while a woven basket filled with magazines is placed nearby. Light filters in through a window with horizontal blinds, enhancing the cozy ambiance.
Condo in Ludlow
4.9 out of 5 average rating, 39 reviews

Fully walkable 2BR condo in Ludlow’s village!

Superhost
An open living space features a bright red sofa with decorative pillows, complemented by a warm wood dining area with stools. The kitchen, equipped with stainless steel appliances, is visible in the background. Soft lighting creates a welcoming ambiance throughout the suite.
Condo in Killington
4.89 out of 5 average rating, 252 reviews

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

Guest favorite
A cozy living room features a large sectional sofa and a coffee table. Above a stone fireplace, a flat-screen TV is mounted on the wall. Natural light filters through a window adorned with simple curtains, while decorative elements add a touch of warmth to the space.
Condo in Killington
4.93 out of 5 average rating, 45 reviews

Cascade - 2nd Floor at the Powder Day Chalet*

Superhost
Condo in Killington
4.95 out of 5 average rating, 22 reviews

Trailside Village #1: Ski In Ski Out 1BR. Hot Tub.

Guest favorite
A spacious living area is highlighted by a stone-clad fireplace, surrounded by a large sectional sofa. Natural light filters through the draped windows, revealing a serene outdoor view. A rustic wooden shelf holds decorative items, and a stack of firewood is neatly arranged beside the fireplace.
Condo in Killington
4.97 out of 5 average rating, 157 reviews

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

Top guest favorite
A serene sleeping area features a spacious bed with plush bedding, complemented by side tables on either side. A warm lamp casts a gentle glow, illuminating an artistic wall hanging that adds character to the room. Soft textures enhance the inviting ambiance.
Condo in Ludlow
4.98 out of 5 average rating, 47 reviews

The Otto: A Warm and Cozy Ski In + Ski Out Lodge

Condo rentals with a pool

Guest favorite
The exterior of the building is shown against a backdrop of a green and orange hillside. Surrounding landscaping includes neatly trimmed bushes, with a paved parking area featuring two parked cars. The structure has a mix of stone and brick accents, complemented by gray roofs.
Condo in Mendon
4.88 out of 5 average rating, 121 reviews

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

Superhost
Condo in Killington
4.85 out of 5 average rating, 106 reviews

1 BR Best Location w/ Pools/Massage Chair/Hottub!

Top guest favorite
The living area features a cozy fireplace surrounded by stone, with a wooden mantel. A dining table with white chairs is positioned near the kitchen, complemented by bar stools at the counter. Light floods in through large windows, enhancing the open layout.
Condo in Ludlow
4.95 out of 5 average rating, 111 reviews

Winterplace - Steps away from Slopes

Top guest favorite
An aerial view of the Trail Creek development, showcasing a cluster of buildings surrounded by vibrant autumn foliage. Key landmarks, including the Ski Home Trail and Sports Center, are highlighted. The distance to the hotel and lifts is emphasized for easy navigation.
Condo in Killington
4.91 out of 5 average rating, 96 reviews

Luxe Trailside Ski On/Off. Next to hot tub

Guest favorite
A modern studio space is presented with wood paneling and a vaulted ceiling. Stainless steel kitchen appliances are featured alongside a dining table and a comfortable seating area. Two vintage ski boards are mounted on the wall, and a sliding glass door provides access to a private balcony.
Condo in Killington
4.78 out of 5 average rating, 323 reviews

Serene Top Floor Condo (resort style amenities)

Guest favorite
The open-concept kitchen features wooden cabinetry and modern appliances, including a stainless-steel refrigerator and stove. A breakfast bar is complemented by pendant lighting. A dining area with wooden chairs is visible, while a staircase leads to a loft area above.
Condo in Killington
4.84 out of 5 average rating, 63 reviews

Adventure Winter Ski & Spa Escape

Guest favorite
The exterior of a multi-story building is showcased, featuring a distinct clock tower and the Mountain Green logo. Balconies are visible on the upper floors, and trees surround the structure. Soft lighting lines the path leading to the entrance, enhancing the welcoming ambiance.
Condo in Killington
4.79 out of 5 average rating, 189 reviews

Amazing,Ski, Golf, Hike, Bike, Adventures

Top guest favorite
A living room area is highlighted by a stone fireplace and a large skylight, allowing natural light to fill the space. Comfortable seating includes a sofa, two armchairs, and a wooden coffee table. A television is positioned on a nearby console, complementing the inviting atmosphere.
Condo in Killington
4.95 out of 5 average rating, 86 reviews

Walk to lift, Ski home, Sunny with loft

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