Find Chalets in Windsor County

Discover this 5-bedroom gem in Chester. This charming chalet offers a serene and lovely retreat for guests. With a mix of king, queen, twin, and bunk beds, everyone will find their perfect spot to unwind. Enjoy the soothing ambiance of the multiple bathrooms equipped with showers and hair dryers. Whether you're relaxing in the AC-cooled rooms or taking in the fresh air outside, this property is the perfect escape. We'll be available to answer any questions while you stay at our place.About pets:No pets allowed.About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.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.

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.

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 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.

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.

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 events:No events allowed.

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.

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 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: 25.About events:No events allowed.

Quechee Cabin, an authentic Vermont offering - 4 Season Resort Townhouse nestled in a picturesque nature setting in historic Quechee Vermont: Ski/Board, hike, bike, relax, swim, sightsee, take a class, work out, dine, and golf at one of two private, prestigious golf courses.Welcome to this cabin inspired quintessential Vermont getaway!This quiet, cozy, Vermont authentic cabin inspired end unit is located in what might be the most picturesque setting in the northeast. There isn't a bad view anywhere in Quechee! We challenge you to find one! Its a "Hallmark" movie wherever you go.Aside from it being part of a 4 season resort community, it's a nature lovers dream. This townhouse is 5 minutes each from Quechee Gorge and Vermont Institute of Natural Science, moments from skiing/boarding, hiking, mountain biking, and snowshoeing. 5 Minutes from the Quechee Lakes Country Club, Ski Quechee, 10 minutes from Woodstock, and just 30 minutes from Killington. The resort community itself has 2 prestigious golf courses, an indoor and outdoor pool and spa, tennis, pickleball and its own ski area: Ski Quechee. Country Club resort use is available to guests for additional but reasonable fees and time reservations. Inquire for more details, happy to answer questions or point you to someone who can!The cabin is complete with games, ski and golf storage, dedicated work space with fast internet, 2 smart TVs, dining area, and has been recently refreshed, still reflecting the time period it was built in. It has a wood burning stove and a two story open loft, which we have listed as a second bedroom. Exposed beam ceilings and hardwood floors, cabinets and countertops make this feel so cozy you won't want to leave! During the non winter months there's a very spacious and private deck off the back, with seating and a portable grill. There is a laundry room 3 doors away which operates using a gift card type of service. Bath is stocked with shampoo, conditioner and body wash, and even an extra toothbrush or razor in case you forget. For a little cabin, it's got a cozy cook's kitchen, and its stocked with coffee, tea, and pantry basics. Hopefully, we have thought of everything to make your stay in beautiful Quechee amazing and stress free. We provide all towels and linens.No smoking, no pets.Whole Condo!!We are available any time with comments, questions, and curiosities. We want you to love your experience there as much as we do.Parking is limited to our unit's spot of 4F, and we have a few shared guest spots placed around the lot. Please inquire if you have more than one car.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 3-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 28.About events:No events allowed.