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, 269 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.

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4.96 out of 5 average rating, 153 reviews

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

Cozy Ski Condo In Historic Mill - on shuttle route

2 bedroom, 1 bathroom condo located in the historic Mill Building (1834). This top floor end unit offers views of Okemo Mtn while overlooking the Black River. With exposed brick walls, wooden beams, high ceilings & a wood burning fireplace we hope you enjoy the coziness of this rustic space after a long day of adventure. Firewood, linens, towels, & cooking needs are provided for added comfort. Our condo is centrally located, walkable to shops/restaurants & is on the shuttle route to Okemo.

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Aerial view captures a large cluster of buildings nestled among vibrant autumn foliage, showcasing shades of orange, yellow, and green. Majestic mountains rise in the background, while a spacious parking area is visible, surrounded by trees.

4.87 out of 5 average rating, 127 reviews

Updated large condo across from AT and skiing

Family friendly, large 3 bedroom condo across the street from hiking and skiing in Killington. WiFi, cable TV, large gathering areas, spacious bedrooms, updated kitchen, and unlimited free firewood in winter. Plenty of après-ski chic touches make this a stylish yet comfortable retreat. 2 minute drive to Pico, 2 min walk to Appalachian Trail! Whether skiing, hiking, playing tennis, swimming, or game nights and cooking at-home meals with friends, this updated condo is a perfect spot to get away.

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4.95 out of 5 average rating, 133 reviews

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

Hotel Chic - Home Comfort -Ski Easy.

HOTEL CHIC - SKI EASY ELEGANT - COZY - SPOTLESS OUR ULTRA COZY RETREAT WAITS FOR YOU. MINUTES TO SKI AND RIDE! WEDDINGS, HIKING, MOUNTAIN BIKING, EASY ACCESS TO AT/LT. BOOK NOW FOR SKI SEASON⛷️ Pico-5 minutes Killington-15 minutes SUPERHOST RATED Air conditioned Fireplace, WIFI TV/living room & bedroom Adjustable queen bed Private covered porch Keypad check in Smoke free/Pet free Seasonal private pool NOTE: Condo regs allow 2 adults(21 yrs). Can not accommodate children/pet

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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.

4.91 out of 5 average rating, 109 reviews

PeeP Hike Golf with Pool and Tennis 2 Bed on Mtn

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!

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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, 185 reviews

Alpine Condo - Close to Ski, Golf & Bike

Updated 1-bedroom condo with stylish alpine feel in the heart of Killington! Just minutes from the ski slopes, Bike Park, Adventure Center, golf, hiking, and scenic drives. ⛷️🚴🏻‍♂️🍂 Enjoy Vermont’s spectacular fall foliage, winter adventures, or a relaxing mountain getaway. After a day outdoors, cozy up by the gas fireplace. Sleeps 4 with king bed + queen pullout. Ski Shuttle available weekends (Dec–April) & ski home trail. Pack & Play available upon request. Reg #007718

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4.93 out of 5 average rating, 124 reviews

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!

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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, 111 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.

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4.95 out of 5 average rating, 194 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.

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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.

4.79 out of 5 average rating, 337 reviews

Serene Top Floor Condo (resort style amenities)

Welcome to Killington! We offer a year round accommodation with the convenience of walking to the lifts, free covered parking, private balcony, full kitchen, and 24/7 keyless entry. The Mountain Green condos have great seasonal amenities in our building such as indoor/outdoor pool, hot-tub, fitness center, ski rental , full service bar/restaurant, outdoor lockers. This is the ideal setup for anyone enjoying the mountain without driving to it!

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4.96 out of 5 average rating, 116 reviews

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

Winterplace - Steps away from Slopes

Newly updated condo at Winterplace Okemo. This sunny corner 3 bedroom unit is just steps to the top of the A-B Quad. Completely renovated from floors to ceiling The delightful fireplace place will keep you toasty in the cozy living area. Outdoor ski locker just outside back door. Front door parking, and firewood included. Pool is open and available to renters all year. Hot tub in winter months and tennis courts in summer.

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