Townhome holiday rentals in Windsor County

Ski-in Ski-Out Cozy Mountainside Condo

Come relax at our cozy retreat after a day of skiing or golf. 36 challenging holes or Ski-in/out from your door. Sweeping mountain views, vaulted ceilings, huge sleeping loft & fireplace, this open concept home is a great escape for couples/families. Strong Wi-Fi & dedicated office space make it easy for distance working. 4 smart TVs & plenty of games/toys for relaxing at home too! Plus our guests have access to all Quechee Resort amenities like gym/sauna/pools/beach/racquet/dining & more…

Bear Woods Lodge

Come stay in this chalet style property on a dead end off the access road! Endless rear woods, exposed beams, plenty of parking, and easy access make it perfect for getting together with friends or family. PLUS! Desks, fast internet, and onsite laundry make remote working/long term stays a dream come true. Restaurants, Pizza, Bars, Ski/Board Shop, Ice Cream, and more are all within an easy 5-10 min WALK. Only a 5 min drive to the lifts or catch the shuttle right at the end of the road

Garden Retreat, Lake Fairlee, Dartmouth & Ski-way

Set in a lovely 3 acre garden setting, our Airbnb is 1/4 mile from the lake and 23 minutes from Dartmouth College or the Ski-way. This private, comfortable apartment is built onto our house with its own entrance, hardwood floors, radiant heat, large windows, full kitchen and bath, & gorgeous garden views. The wrap around loft has 3 generous semi-private sleeping areas with 2 queens + 1 twin. A queen futon is downstairs. Rental includes pass to Treasure Island Recreation area & beach: 1.5 mi..

Mountain Edge Living

Enjoy life in the mountains with outdoor adventures abound. Bike Hike Ski 3BR Sleeps 6 Trailside Slopeside Townhouse in Brownsville/West Windsor Vermont next to Ascutney Outdoors and Ascutney Trails. Walk into the spacious ground-floor entry and store your gear. Master Bedroom, Kitchen, Dining Area, Family Room, Hall Bath, and Laundry ALL on the entrance/ground level for an easy move-in experience. Step down to the lower level to the game room, another full bath, and 2 spacious bedrooms.

Luxury Okemo Condo at Castle Hill Resort

This beautiful 1850 square foot 3 bedroom condo at the historical Castle Hill Resort is located close to everything Okemo and Ludlow have to offer. This home is well equipped and is in pristine condition. This rental showcases a central spacious kitchen with granite countertops and stainless-steel appliances. Guests are sure to enjoy the large living area on the main floor that offers plenty of seating for everyone to gather around the gas fireplace after a long day of outdoor adventure.

Cozy condo near Ludlow, Okemo & Killington

This charming condo nestled at the top of a mountain at the Hawk property contains 3 bedrooms and 2 baths for a family stay. Our cabin style townhouse features a stone fireplace and greenhouse windows with unforgettable views of the surrounding nature and sunsets. An ideal place for anyone seeking outdoor activities or some time to just relax! It is secluded and yet a short drive from the ski resorts of Killington and Okemo, along with the village of Ludlow, and the picturesque Woodstock.

Lovely Trailside 2 Bedroom Townhouse

Enjoy a fun outdoor adventure at this centrally-located condo on Mt. Ascutney. Trails are just outside the door, with miles of back-country skiing and snow shoeing, including Ascutney Outdoors lodge, lift-assisted tubing/sledding, and beginner skiing (t-bar). Maple Kitchen restaurant and Brownsville Butcher & Pantry are within a mile. Great sporting, shopping, eating and family activities nearby at Okemo, Killington, Woodstock, Hanover, Harpoon Brewery, King Arthur Flour and more.

SKI ON/OFF Spruce Glen B | AC | Sauna| Fireplace

Come and enjoy the largest private trailside property in Killington (almost 4 acres), with more convenience and value than large house rentals and more privacy than condo villages. The direct ski on/off is the easiest you'll find in Killington. Quiet and serene, the mature New England Evergreens and gentle mountain stream are a tranquil relief. An ideal ski in ski out or any season vacation getaway. Great Eastern is the longest green run in the East. Welcome to Spruce Glen!

Renovated 2bd/2.5bath/Den + Pool Access (pets ok)

Recently updated ski condo - modern kitchen appliances and new furniture. Minutes away from Killington Ski base. Drive there or use a paid bus service, steps away from the condo. Part of the luxurious Woods Spa Resort and stay includes use of resort amenities including gym, pool, steam/sauna and hot tub. Spa service available but not included in fee (please check for open hours) Warm, cozy and welcoming-custom built for ski lovers to relax after a long day on the mountains.