Find Chalets in Windsor County

Secluded ski chalet with centralized location to Okemo Mt., Killington Mt. (around 15 minutes to each), Woodstock and lots of outdoor adventures nearby! Peaceful and woodsy location perfect for nature lovers, offering outdoor fire pits. Multi-family and pet friendly.Enjoy the drive in, as you travel through the beautiful dirt roads, where you find this home nestled in the hills of Calvin Coolidge State Forest. Just a walk down the dirt road leads you to Americas oldest Cheddar Cheese factory, PLYMOUTH VT ARTISAN CHEESE 🧀 😋 The House comfortably sleeps 10 with the following accommodations:- First Floor, Queen Bed with twin bunk - First Floor, Full bath- Main Floor, Bedroom 1 Queen- Main Floor, Bedroom 2 Queen- Main Floor, Full bath- Loft, One Queen, three twins (It should be noted, the loft area possess a risk of injury, as a wooden loft ladder is utilized for access).- Loft, Powder roomThe house has two living rooms which is great for accommodating multiple families, adults/kids or finding a quiet couch to nestle on beside a fire while reading a book. First floor living room is equipped with board games as well as video games and a toasty wood burning stove. The house has multiple Smart TVs, free high speed WiFi, coffee maker, (2) refrigerators, oven, grill, griddle, microwave and a table that comfortably seats 8. Near by fun:- Ski mountains within a short drive; Killington, Pico, Okemo, Suicide 6 (Saskadena Six)- Snowmobile’s access the Vermont Association of Snow Travelers (VAST) trails less then a mile away- Breweries/Distilleries; Long Trail Brewing (7 miles) Harpoon, Whistle Pig Tap room, SILO Distillery- Sherborne Mountain Biking Trails - Kayaking the near by lakes- Hiking Mt. Killington via Sherborne Trail - ATV Vermont (VT Tours) cruise the mountains on your own ATV- Farm & Wilderness Plymouth camp- Echo Lake BeachEssential information: This private ski chalet is nestled in the state forest along a dirt road that is well maintained in the winter. That said, we recommend and encourage people to have all wheel drive or front wheel drive capabilities. Due to the secluded area, cellular reception is limited but WiFi calling capable. Exterior camera on driveway for security and driveway maintenance. About pets:Pets allowed: dogs (limit 1 total).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.

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.

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.

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.

Get away to the Caven Cabin! Secluded quintessential Vermont log cabin nestled below a pine filled ridge. Have your morning coffee on the large wrap around deck overlooking Elm Brook before your day hiking, brewery hopping, or hitting the slopes! The cabin provides open floor plans centered around the large stone face fireplace, the perfect space for gatherings of family, friends, or a couples retreat! Each floor provides its own unique bedroom for a private relaxed nights stay. See you soon!So much to do so close by!- Snowmobile in/out to Vast Trail in 5 min- 8 min to downtown Ludlow- 10 min to Okemo- 15min to buttermilk falls- 6 min to Singletons store- 5 min to Outter Limits Brewery- 8 min to Eight oh Brew Brewery- 2 min to fly fishing the Black River- 15 min to lake rescue - 25 min to KillingtonLarge parking area directly outside of the cabin for easy in and out access. The street is extremely private and is plowed by the town in the winter months. No steep inclines in or out of the property from the main road. Dirt road access easy to navigate.About pets:Pets allowed: limit 1 total.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Only registered guests allowed on property. No open flame allowed in cabin or on deck. No smoking on property ($500 charge). No weapons of any kind..No fireworks, glitter, or confetti allowed. Do not leave food or garbage on the deck. Only toilet paper in the toilets. Quiet hours 10PM-8AM.,Late checkout will incur a $50 per hour charge unless approved by host. Pets brought on the property without registering them will incur a $300 charge.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 23.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.

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.

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!.