Find Chalets in Windsor County

Combining sweeping views of distant hills with complete privacy and wraparound porches on two sides, the Red House is a custom cabin built for couples and smaller families. Surrounded by working farms and within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont and awaits the discerning traveler. 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.

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.

The log cabin at Trail End Ranch, which boasts the most comfortable beds, a well appointed kitchen/ living area. Summer perfect deck to enjoy the night sky, morning coffee, or afternoon relax time while watching the horses graze on our beautiful ranch pastures. Comfort and the outdoors, manicured lawns, Weber charcoal grill (charcoal/lighter fluid and grilling tools provided), Adirondack chairs and fire pit (kindling and wood provided). The BEST ski resorts to choose just 6- 30 minutes, access to VAST Trails 1/2 mi away for the days adventures to unfold, snowmobiling at its best is right here! Lowell Lake State Park, restaurants nearby and nightlife at Magic Mountain ski area just 6 minute drive. Ranch life will be alive around you and you'll feel on your own and right at home. Welcome to the Log Cabin at Trail End Ranch!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.No smoking allowed on premises, no pets..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

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 & fireplacePet-friendlyFast Wi-FiNear 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.

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.

Ideal to host up to 6 guests, this home on 2 acres of land is a perfect retreat for anyone looking to be in the heart of nature. Chester and Ludlow, VT are minutes away and call you to explore historic landmarks and enjoy skiing at Okemo Mountain (located 15 minutes away). With modern facilities & a private location, this will be your home away from home!The Space:This 2-story home features 2 comfortable bedrooms, well-kept bathrooms, a fully furnished kitchen, cozy living space w/ bunk bed, dining area, and a majestic deck to spend some time in the company of captivating nature views. New in 2024, enjoy a side yard patio equipped with a large fire pit, 7-person Jacuzzi Hot Tub, and picnic area. Stay connected to the world & easily work from home as high-speed Wi-Fi is available at the property. The vast greenery and clear blue sky are a treat for nature lovers. Everything at this home has been thoughtfully designed and managed to make your stay as homely as possible. Book this home for your next Chester, VT stay – your ease, comfort and happiness will be our foremost priority!Mountains Nearby:-Okemo (~15 minutes)-Killington (~35 minutes)-Bromley (~40 minutes)-Stratton (~50 minutes)-Mount Snow (~60 minutes)Key Highlights for an Amazing Stay -2-Acre Area w/ 100% Privacy-Jacuzzi Hot Tub large enough for 7 people-Outdoor patio area with Large Fire Pit and Picnic Area-Indoor Gas Fireplace-Less than 15 Minutes from Okemo Mountain-Outdoor Propane Grill-Star Gazing with nearly 0 light pollution-Peaceful Vicinity-Fascinating Nature Views-Well-Appointed Bedrooms -2 Queen Beds + additional Bunk Bed-Gourmet Kitchen w/ Modern Appliances-Large Deck w/ Seating -Super-Fast Wi-Fi (350 Mbps+)-Smart TVs w/ Netflix Access-AC + Heating-Lots of Reading Material + Board Game Activities-Laundry (Built-in Washer & Dryer)-Essentials (Towels, Linens, Basic Toiletries, Kitchenware & Cutlery)-Free Parking (Note: 4WD/AWD Vehicles are REQUIRED as the hill is steep)Guest Access:Guests will have access to the entire house. Please feel free to reach out in case of any further questions, we are here to help!Other Details to Note:• The road and driveway leading up to our home is quite steep and hence 4WD/AWD Vehicles (SUV recommended) are a MUST in the winter and highly recommended otherwise, throughout the year. During times of heavy snowfall, the road may be inaccessible. However, the roads generally get plowed within a few hours of snow build-up. • Maximum Occupancy is 6 at a time. • Hosting Events or Parties is not allowed.• Please do not cause any damage to the property or the furniture. It has been decorated with so much love and care for your stay.• MIN AGE 25About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:AWD/4WD SUV Vehicles are highly recommended in the warmer seasons and required in the colder seasons..Primary guest must provide copy of Drivers License within 24 hours of booking,Guests must have prior reviews on VRBO that are positive.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.

Gather with family and friends at our spacious home nestled in the Vermont woods.The Blue Moon Bungalow is your home away from home, with everything you need for a relaxing getaway, with the beauty of nature all around. Our large, open floor plan, secluded 2 acres and spacious bedrooms make it the perfect location for multiple groups and families to enjoy.We're a short 13 minute drive from Okemo/Jackson Gore and a 9 minute drive to downtown Chester with plenty to do and explore!The Blue Moon Bungalow is a renovated camp with rustic charm and modern amenities. With enough beds to sleep 10 and a large great room on the first floor, it's the perfect escape for a group or multiple families. All linens and towels are provided.Inside our cozy interior you'll find three flat screen tvs with Rokus to log into your preferred streaming services. Watch a movie, share a family dinner and play board games in our great room around the gas fireplace.Take in the natural beauty of Vermont while relaxing on our sunny deck, playing yard games, exploring the property and making s'mores by the firepit. Be sure to check out the amazing stargazing from the deck on a clear night!Perfectly located between Chester and Ludlow/Okemo there's something to do for the whole family. Outdoor lovers will enjoy the skiing, mountain biking, snowmobiling, hiking and leaf peeping. During the summer months book a scenic chairlift ride to the top of Okemo, take a ride on their mountain coaster and challenge yourself on their ropes course.Within a 15 minute drive of the Blue Moon Bungalow you'll find plenty of antiquing, fine dining, breweries, live music, golf and more!Please note: - We have two security cameras, one next to the front door and one on the front of the house. They will be on during your stay. - We highly recommend 4WD or AWD to get up the hill to our house in the winter.- Pets are allowed with owner approval + a $75 pet fee. Please contact us for more information.About pets:Pets allowed: limit 1 total.Pets are allowed with owner approval + $75 pet fee.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:All gatherings must be kept to your reserved group. No additional guests allowed on the premises. Pets ok with approval + $75 fee. Msg for pet rules..No smoking, unauthorized pets, fireworks, firearms and/or explosives are allowed in/on the property. A $300 fee will be charged to offenders.,All trash & recycling must be securely sealed in bags and left inside the cans in the trash enclosure next to the driveway..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 24.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.

Wake up to lake views just 2 miles from Okemo at Lou Lou’s Landing. Enjoy year-round fun—kayak and swim in summer, ski nearby mountains in winter, or relax on the deck and by the fire pit. This 2BR + loft home sleeps 8, with a full kitchen, spacious living area, and private dock on Lake Pauline. Perfect for families, couples, and all-season getaways.Our family’s love for this lake began in the 1970s, when our Aunt Mary Lou (“Loulou”) purchased the A-frame next door. Since then, Lake Pauline has been the heart of our family for generations — and we’ve designed this home so you can create your own lasting memories here.Inside, you’ll find:Open-Concept Living – Large windows frame lake views in the living room, plus a SmartTV and games for cozy nights in.Fully Stocked Kitchen – Stove/oven, microwave, dishwasher, cookware, utensils, coffee, creamers, and pantry basics.Two Queen Bedrooms – One on the main floor (ensuite bath with shower) and one upstairs (ensuite bath with tub).Loft Sleeping Area – Twin bed + twin trundle, plus a pull-out sofa in the living room.Outdoor Highlights:Large deck with lounge chairs & propane blackstone grillFire pit for marshmallow nightsKayak & lake floats includedFlat backyard for games and gatheringsThings to KnowWinter:4WD or AWD recommended for snowy conditions.Driveway is plowed, but walkways can be slippery — tread carefully.The lake does not fully freeze — no ice access allowed.Summer:Life vests recommended for all water activities.Please return floats and kayaks to shed storage after use.About pets:No pets allowed.About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.About events:No events allowed.

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.