Find Chalets in Windsor County

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!.

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.

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.

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.

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.