Condo holiday rentals in Woodstock

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, 268 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.

4.89 out of 5 average rating, 102 reviews

Luxe Trailside Ski + Bike On/Off. Next to hot tub

Enjoy the best location in Trail Creek! Nearest building to the Snowshed lifts (5 min walk on), Snow Tubing, Grand Hotel Spa, Adventure Center/Bike Park, Ski Home Trail and Sports Center with pool & hot tubs. Renovated living area with VT stone fireplace, new rustic modern kitchen, updated baths, beds and more. Unit backs to private woods and directly to the ski home trail. No stairs & right next to pool/hot tubs (no long walk in the cold). Pop next door for Starbucks or Apres ski at Prestons!

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!

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, 178 reviews

Alpine Condo - AC & Pool - Golf & Bike

Updated 1-bedroom Whiffletree condo with stylish alpine feel—steps from Killington Resort, golf course, and access road. Thoughtfully stocked with essentials, plus a private gear locker for convenience. Relax at the onsite outdoor pool (open Memorial Day–Labor Day). Sleeps 4 with a king bed and queen pullout sofa. Portable AC unit in the living room helps keep the condo comfortable Pack & Play crib, mattress and sheets available upon request for $25 per stay. Reg #007718

A spacious living area features a large stone fireplace with a flat-screen television mounted above. Comfortable seating is arranged around a wooden coffee table, creating an inviting space. In the background, the kitchen and dining area are visible, offering a seamless connection to the living space.

4.94 out of 5 average rating, 111 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

Ski On-Ski Off!! Beautiful remodeled condo is in the heart of Sunrise at Bear Mountain. The designer kitchen features granite counter tops and top of the line stainless steel appliances. The main focal point in the living room is a massive stacked stone fireplace with a flat screen on the mantel. Recent upgrades include new living room furniture, master bed room furniture & updated tile in both showers. Additionally I own the adjoining unit & if you want more info see below

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, 173 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).

4.89 out of 5 average rating, 122 reviews

A cozy living area features a brown leather sofa with decorative pillows and a woven area rug. Nearby, a small table stands beside a stylish lamp. A pass-through connects to the kitchen, equipped with bar stools, enhancing the open and functional layout.

Condo in Warren

Slope-side posh little condo at Sugarbush!

Walk to the chairlift from this sleek little condo in the historic Sugarbush village, just 500 yards from the base of Lincoln Peak. This newly renovated and thoughtfully decorated condo is the perfect place to relax after a day of skiing, hiking, canoeing, or rock jumping. This location is amazing! There is one restaurant IN THE BUILDING, the chair lifts and the Recreation Center with pools, tennis, & fitness gym are a short 500 yard walk away.

4.95 out of 5 average rating, 193 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 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, 336 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!

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, 232 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.

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, 226 reviews

Mtn Green Condo-Ski/Bike Lifts, Covered Parking

Your four-season basecamp at Mountain Green Resort — walk to the lifts for skiing or summer mountain biking, plus hiking and golf nearby. This renovated 1-bedroom sleeps 4, with a reserved garage parking spot and a winter shuttle to Snowshed every 15 min. Enjoy a renovated kitchen, Wi-Fi, and smart TVs. Resort amenities include an indoor pool, hot tub, sauna, and gym year-round, plus an outdoor pool Memorial Day–mid-September.