Find Chalets in Windsor County

Escape to this peaceful, pet-friendly hideaway nestled in the snowy Vermont woods — 6 miles from Okemo and 14 miles from Killington Skyeship. Spend your days skiing or snowboarding on world-class slopes, snowshoeing through quiet forest trails, or exploring charming nearby towns like Woodstock and Manchester. After a full day on the mountain, cozy up by the crackling fireplace. Your perfect Vermont winter getaway awaits.🔥 Fire pit & fireplace🐾 Pet-friendly⚡ Fast Wi-Fi⛷️Near skiing Book your perfect winter getaway today!"We had a beautiful time just disconnecting and reconnecting with each other. Definitely looking forward to coming back."-Katie "Cute chateau and great location. This was our first trip to Vermont and we couldn't have asked for a better host or place to stay. Jeanne was great about communicating to suggest things to see and making sure we had what we needed. Even a later check out time. We will definitely stay again when we're out this way."-LonnieAbout pets:Pets allowed: dogs (limit 2 total).No pets on furniture. Please pick up after pet..About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Known as 'The Cabin', this 5,000 S.F. home that is surrounded by ten private acres within brilliant wilderness, the majestic mountain range in your own backyard. Designed with the purpose of bringing people together, it perfect setting for hosting gatherings for friends, families and special events. Experience the perfect balance of privacy yet still have the comfort of knowing you're just a five-minute walk from the local convenience store and the Long Trail Brewery. A short drive away from the slopes of Killington & Okemo Mountains as well as many other famous attractions year round.A popular destination for weddings, corporate events, family reunions and other gathers. *please make sure to ask about our special wedding and corporate event ratesThe Cabin features a 22’ ft teepee offering a unique way to gather and experience Vermont. Imagine gathering around a fire inside a large cozy teepee getting a firsthand experience of what life was like as a native American living on the land. To those that have been coming to The Cabin over the years can now look forward to a new experience during the spring, summer and fall seasons. Once inside they are fully furnished and cozy foam mattresses and authentic hand-painted art and coverings. Perform group activities within the teepee including yoga sessions, drum circle, meditation, singing around the campfire to name just a few.The Cabin is set on a private plot with is surrounded by Mountains and a huge valley which includes a private backyard creek. Located seven miles away from The Skyeship Base Lodge about six miles east of where the Killington access road intersects with Route 4. Avoid the lines and take the Skyeship Gondola, with a stop at the mid station, runs to Skye Peak. About pets:Pets allowed: dogs and cats (limit 4 total).Please make a request with your inquire.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:- PLEASE, ABSOLUTELY NO SMOKING.No check in or check out on Saturday..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.Smoking fee of $250 from your security.About minBookingAge:Minimum age to rent: 25.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 99,Yes, but must be approved by owner in writing.

Sweeping Vermont Views | Designer Mount Ascutney Cabin | Fire Pit | Near OkemoWake up to sweeping Vermont mountain views from this designer-built cabin on the slopes of Mount Ascutney. Thoughtfully designed with a chef’s kitchen, wood-burning fireplace, and private fire pit, this peaceful retreat is ideal for skiers, snowshoers, couples, families, and remote workers looking to unwind and reconnect.Ski where you feel like:Okemo is just 30 minutes away, while Killington and Mount Sunapee are about 40 minutes.Set into the mountainside, the home is steps from hiking and snowshoeing trails and centrally located to some of Vermont’s most loved towns, dining destinations, and outdoor experiences.The HomeChef’s kitchen with gas range, quality cookware, and full place settingsCozy Jøtul wood-burning fireplacePrimary suite with private balcony and mountain viewsSecond full bath with a spa-style rainfall showerSleeps up to 6 guests, including a second bedroom with twin bunk bedsLarge sliding glass doors that frame the forest and snowfall beautifullyOutdoor LivingPrivate fire pit for evenings under the starsSpacious deck for coffee, meals, or après-ski drinksNatural rock walls and tree lines provide a strong sense of privacyThe nearest road is approximately 300 feet from the houseNearby Attractions (10–40 minutes)Woodstock, VT – Covered bridges, artisan shops, galleries, and The Woodstock Inn & SpaQuechee, VT – Simon Pearce flagship dining and glassblowingLudlow & Okemo Mountain Resort – Skiing, gondola rides, mountain bikingHarpoon Brewery (Windsor) – Casual dining, tastings, and eventsTwin Farms (Barnard) – Renowned fine dining and spa experiences (reservations required)Montshire Museum of Science, Hood Museum of Art, farm stands, and riverside parksAbout pets:Pets allowed: dogs and cats (limit 2 total).Love pets but request pets not get on the beds..About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

Situated on 12 acres with views of Okemo Mountain and direct access to VAST snowmobile trail. Minutes to charming village of Ludlow and Okemo Mountain base for skiing and sledding in the winter. In the summer there is mountain biking and a host of activities at Jackson Gore, including the mountain coaster, miniature golf and ropes course. Enjoy golf nearby at Fox Run golf course, kayaking at the finger lakes and hiking in the Okemo Valley summer and fall. Main floor has 2 bunk rooms and open concept living room, kitchen and dining area with stone fireplace. Wrap around deck with gas grill and fire pit a short distance away. Upper level with 2 en suite bedrooms with fantastic views of Okemo and master has gas woodstove and private balcony. Lower level has bedroom, bath, living space with ROKU TV and multigame table. Perfect space for multiple families. Plenty of outdoor space to snowshoe, cross country ski or hike. Private trail to VAST snowmobile trails which run through the meadow in the back of the property. In the summer months great space for lawn games, camping and enjoying the view of the mountain by the firepit. About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Please strip sheets on used beds, put in laundry room along with used towels. Put used dishes in dishwasher and turned on before leaving..House is on septic tank. Please no food or oil down the kitchen drain and no paper wipes, diapers or feminine hygiene products down the toilets.,No parking in garage, sensitive carbon monoxide alarm. Put garbage in garage. Keep garage keypad closed. NO CHARGING ELECTRIC/HYBRID VEHICLES AT HOUSE.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

A true Ski in / Ski out house on the beginner Sachem trail at Okemo Mountain. This beautiful eight-bedroom chalet is ideal for your upcoming getaway. Situated right on the renowned Okemo Mountain Resort. You'll have easy access to world-class skiing, snowboarding, and a wealth of outdoor adventures.As you step inside, you'll be greeted by a cozy and well-appointed interior, complete with two fireplaces, multiple smart TV's and a game room. There are two fully stocked kitchens, equipped with two stoves, three ovens, three refrigerators, grill and all the necessary appliances, invites you to unleash your culinary creativity and savor delicious meals with your loved ones.Unwind in the game room, where you can challenge your friends to a game of foosball or explore the selection of video games and other entertaining diversions. For a more relaxed evening, gather around the fireplace and enjoy the serene ambiance overlooking the ski slopes and the Town of Ludlow.With 4 full bathrooms and 2 half baths, and ample towels, you'll have everything you need to feel right at home. And with the added comforts of linens and basic toiletries, this chalet is perfect for families and groups of all sizes.Whether you're seeking a cozy retreat or an action-packed getaway, this Ludlow chalet offers the perfect blend of comfort, convenience, and access to the best the area has to offer. Book your stay today and experience the ultimate vacation in the heart of the mountains!About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Early check in if available is $300 and late check out if available is $300.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 25.

Completely renovated 7 bedroom, 3 bathroom modern mountain house, located in Ludlow. Outdoor deck with BBQ, hot tub, across the street from the mountain shuttle. All rooms with smart Tvs, game room with billiards and board games, large chefs kitchen with dining room and kitchen island. Mudroom at back entry.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Please turn the thermostats to 62° before check out.Please make sure the hot tub is covered after each use,Please throw all the garbage in the outside bin and make sure that lid is closed.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

This rustic, cozy little cabin sits on Lake Pauline, approximately 2 miles from Okemo Mountain (Jackson Gore), on a dead-end road. You are close to everything but feel like you are away from it all! Lake Pauline is a 'quiet' lake, with fishing, swimming, canoes & kayaks allowed - no motor boats. There are kayaks, a canoe, and life vests at the cabin, with plenty of rental options close by. The cabin has 2 bedrooms on the main floor that contain full sized beds and a loft containing 4 twin beds. There are (2) full baths on the main floor and in the heated, walk-out basement, both w/ walk-in showers. There is wood burning fireplace and streaming tv in the main room and a tv/dvd combo in the loft. The kitchen has full-sized appliances and is stocked with the necessities, the table is expandable to seat 8. Washer/Dryer in the basement & secure wifi internet access. Outside there is a grill, deck, firepit & dock.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.Cabin is not child-proofed, watch your children!.About checkIn:Check in after 4:00 PM.About smoking:Smoking allowed: in designated areas.Don't care what you are smoking but do it outside!.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.Small cabin with neighbors nearby - no parties!.

Falcon House is a 2+ bedroom, 2 bath architect designed chalet, accommodating 5 guests in comfort and spa-like style. Located beside a year round brook on 25 acres of private forested property with private hiking, single track biking & snow shoe trails. All just 2.5 miles (5 min) from Woodstock Village; you can easily bike to town on pretty country roads! Just 13 miles to Killington's Skyeship base (19 min).New >>Outdoor Finnish sauna ! This unique and beautiful Scandinavian style spa home is airy, spotlessly clean, peaceful and very comfortable. Locally owner managed and hosted, assuring you have a 5 star experience! Re-connect with nature as you explore the private hiking/snowshoe trails, Enjoy sun salutations on the yoga platform or refresh in the outdoor shower (seasonal). Return home to warm yourself by the fire, dine on the brookside deck and enjoy a wonderful meal prepared in the well equipped kitchen. Large windows all around bring the beauty of the Vermont's outdoors into the home. The house features 2 beautiful bedrooms: The lofted king master suite with en-suite bath on upper level and a queen bedroom on the main floor. Also a quiet den with a private and comfortable full sized futon and TV on the lower level . 2 full baths, one on the main floor plus the bath en-suite to the 2nd floor master. Fully equipped chef's kitchen with stainless steel appliances and a view to woodlands for the chef to enjoy. The living room has a cozy gas fireplace, flat-screen TV and lots of comfy seating and open floor plan. Dining table with seating for 6+, plus (seasonal) deck dining for 6.An elegant spiral staircase leads to the loft style master suite with custom made live edge cherry king bed and spa-like en-suite bath. The main floor bedroom has a pretty queen sleigh bed; main floor full bath is adjacent. Lower level den offers a very comfortable full size futon and TV, adding additional private sleeping for 1 or 2 and living space. Private deck with brook-side dining and BBQ. Wood burning fire-pit just off the deck, we supply your fire wood for and evening fire under the stars!Falcon house is meticulously maintained, fresh and spotlessly clean! The owner will personally and thoughtfully prepare the house for your stay.Owners/Hosts live locally and are available any time, while leaving you in privacy to enjoy the house.Ideal location just across historic Lincoln covered bridge! Falcon House sits on 20 wooded acres accessed by our private hiking/biking/ snowshoe trails, with a year round brook running right past the house. Located 2.5 miles (5 min by car) from lovely Woodstock Village and 15 minutes to Killington ski resort. Woodstock's bike route runs right in front of the house, just a few minutes pedal to the village, also a favorite running route. Follow Falcon House on Instagram & faceBook @Falconhousevt and @GrayBarnsVT for more photos, updates and just some fun.-House amenities include 2 flat screen TVs with Satellite and DVD players, fast Wifi & internet.-A full laundry area is available for guest use, brand new machines; lower level. -Private spa amenities include a yoga platform at the edge of the woods, outdoor shower (seasonal) and outdoor Finnish sauna. -Miles of forested trails to explore as a forest bathing experience, or a serene hike or snow shoe..-Plan your Vermont nature retreat! You could your day with a few sun salutations on the yoga platform or take a hike on your private woodland trails on the 60 acre private property. BBQ and dine on the deck then complete your day with an evening campfire by the brook or a relaxing sauna bath. We've provide bikes (4), yoga mats and outdoor seating for your convenience and enjoyment. Please also visit our other Woodstock VT vacation properties: Dana Road House Vrbo #223034 is a 3BR / 2BA for 6 guests, just 1.7 mi. to village and Vrbo# 2603052. Windfall at Quechee Lakes resort accommodates 4 guests.Explore beautiful Woodstock Vermont! Go skiing, biking, hiking, horseback riding or walk around the village and enjoy the fine shops and restaurants. Voted 'the prettiest town in Vermont' Woodstock is truly a special place. Visit Marsh-Billings National Park, shop and dine in beautiful Woodstock village or take a short drive to nearby Quechee to hike Quechee gorge, explore VINS raptor center or enjoy a great meal and glassblowing at Simon Pearce. And so much more! Please ask us about our online guest guide with our curated list of local favorites.Vermont rooms & Meals Tax license # MRT10094275001About pets:No pets allowed.No pets please.About checkOut:Check out before 12:00 PM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.No smoking..About minBookingAge:Minimum age to rent: 29.About events:No events allowed.All events must be pre-approved by owner (Kat).

With a stay at this cabin in Ludlow, you'll be next to a golf course, within a 10-minute drive of Okemo Mountain Resort and Dorsey Park. This golf cabin is 3.7 mi (6 km) from Blue Lot and 4.2 mi (6.8 km) from Skywalker Carpet. This smoke-free cabin features snowboarding nearby, cross-country skiing nearby, and hiking/biking trails nearby. Make yourself comfortable in your cabin, featuring a refrigerator and a Smart TV. Complimentary wireless internet access is available to keep you connected. Conveniences include a desk and a coffee/tea maker.