Find Chalets in Windsor County

Off-Grid Hideaway in the Vermont Hills — Peace, Privacy & Pure SimplicityPlease read the full description before booking ;)If you’ve been craving a true escape — a place to slow down, unplug, and reconnect with nature — welcome to our private, off-grid cabin tucked away just 2 miles off Route 103. Quiet, cozy, and surrounded by trees and sky, this four-season retreat is the perfect balance of wilderness seclusion and easy access to Vermont adventures.Step inside our newly built cabin, thoughtfully designed for comfort and simplicity. The open, airy layout features a full kitchen, woodstove, and propane heat for year-round comfort. There’s one ground-floor bedroom, plus a loft with twin mattresses and a double bed — perfect for couples, small families, or a solo retreat.This is authentic off-grid living, with a few modern comforts: Hand pump inside (water must be heated for washing and bathing)Potable water providedClean, odor-free composting toilet inside and outhouse outsideSpend your days exploring nearby world-class skiing (downhill and cross-country just 15 minutes away), hiking trails, and scenic drives through two charming nearby villages with excellent restaurants. Or simply stay in — curl up by the woodstove with a book, listen to the babbling brook at the foot of the drive, and watch the light shift through the trees from the cabin’s many windows.At night, step outside to a sky full of stars and the sound of silence.It’s peaceful, grounding, and deeply refreshing — a balm for the busy modern world.Come experience Vermont the simple way — off-grid, off the beaten path, and absolutely unforgettable.About pets:Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.2 children max.About customRules:Guests use ladder accessing loft at their own risk.Propane heat turned down to 55 when not in the cabin for the day and Dishes all washed and kitchen tidied.. We need to stay ahead of the mice!!,Leaving: humanure bucket emptied , linens in mudroom. 'Fridge cleaned out, dishes washed, take garbage/ trash with you. Leave recycle items.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.

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.

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.

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.

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!.

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.

Cozy private cabin located just 10 minutes from Okemo! This cabin features a mud room to store all your ski gear. One bedroom with a double bed, double sized bunk bed, and mini crib. The living room features a 60” TV and pull out couch. Bring your snowmobiles for direct access to the VAST trails across the street.About pets:Pets allowed: dogs (limit 1 total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:-Keep food and drinks in kitchen and dining area. -Please do all your dishes - Any dirty towels place in tub - Do not leave trash/ food outside.When leaving the house and when checking out unplug all space heaters and turn heat down to low "L" in the winter. In the summer keep heater unplugged.About checkIn:Check in after 3:30 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

Wake up to sweeping Vermont views from this designer-built Mt. Ascutney cabin — with fire pit, chef’s kitchen, and cozy wood fireplace. Great for skiers and snowshoers, solitude seekers, couples, families, and remote workers looking to unwind and reconnect. This designer-built Vermont cabin offers a perfect base for exploring the best of the Green Mountains.Tucked on the slope of Mt. Ascutney, you're steps from hiking and snowshoeing trails at the center of Vermont’s iconic attractions, culinary destinations, and charming towns.Inside the home:- Enjoy a chef’s kitchen with gas cooking and quality tools- Relax by the Jøtul wood-burning fireplace- Retreat to a primary suite with a private balcony- Refresh in a rainfall shower in the second full bath- Sleep up to 6 with a second bedroom featuring twin bunk bedsNearby Attractions (10–40 minutes):- Woodstock, VT – Covered bridges, artisan shops, art galleries, and The Woodstock Inn & Spa- Quechee, VT – Home to the Simon Pearce flagship for upscale dining and glassblowing- Ludlow & Okemo Mountain Resort – Skiing, gondola rides, mountain biking- Harpoon Brewery (Windsor) – Casual dining, events, and beer tasting- Twin Farms (Barnard) – Exclusive resort for fine dining and spa access (reservations required)- Montshire Museum of Science, Hood Museum of Art, farm stands, and family-friendly riverside parksOr go nowhere, just gather by your private fire pit or sip coffee/beers on the deck surrounded by nature and watch snow falling outside through our huge sliding doors. Pet-friendly: We love our four legged friends and welcome respectful pet owners! Any pet damage is the guest’s responsibility, but it’s rarely an issue. The French around the house is natural, rockwalls and tree lines separating the property from nearby houses. the road in front is close to 300 ft from the house.This is a peaceful, high-quality retreat- not meant to accommodate any events or large gatherings.About 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.

The log cabin at Trail End Ranch, which boasts the most comfortable beds, a well appointed kitchen/ living area. A 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.