Chalet vacation rentals in Windsor County

Killington Chalet - Hot Tub, Sauna, Boot Dryer

The Killington Chalet is your ideal vacation rental in the Green Mountains. It's the Right side of a duplex, perfect for families, couples, and groups. Located just off Killington Rd, it offers a secluded retreat near slopes, restaurants, and outdoor activities. Enjoy skiing, boarding, mountain biking, and more. Features include hot tub, sauna, boot dryer, wood stove, fire pit, and a fully equipped kitchen. Fresh linens, towels, and toiletries provided. Book for a memorable stay in every season!

Prime Killington Proximity | Ski, Sauna, & Soak!

Awarded Airbnb’s "Most Loved Homes!" Escape to our warm chalet, just 5 minutes from the slopes in Killington's most desirable neighborhood. Ski, hike, bike, or golf by day–then unwind in our private sauna, soak in the outdoor hot tub, or curl up by the wood-burning fireplace in front of the TV. Comfy beds, full kitchen, fast WiFi, and billiards & darts in the game room. Close to great restaurants, breweries, nightlife, golf, and breathtaking fall foliage. Your perfect mountain getaway awaits!

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Cheerful 4-bedroom chalet with lake view

Welcome to Fall Line Lodge. Five min to Jackson Gore/Okemo, 5 min to Plymouth State Park, 25 min to Killington. On a quiet private road. Property overlooks charming lake through a large span of windows from the main living area. Cozy stone fireplace, open concept dining and living room with vaulted ceilings. 4 bedrooms - 2 queens, 1 king, & twin bunk bed. Grill & fire pit area overlook the lake. Perfect for 6-8 people. Laundry room. Bring your well-behaved fur baby. (Max 2 dogs, $90 pet fee).

Kingsbrook: Chalet w Sauna, Hot Tub, AC!

Located off East Mountain Road, on a secluded dead end street, just minutes from your choice of the Killington base lodges. There is access to a ski/hiking trail at the end of our street (1/2 mile from the house), and we're surrounded by hiking and biking trails. The house is great for large groups and families, as there are 2 separate living areas (kids like to hang out in the lower family room with large screen TV and games). Very strong and fast internet. Now with AC for summer getaways!

Falcon House: VT Chalet w/Sauna, Bike to Village

Welcome to Falcon House! A modern VT chalet w/sauna at the edge of a 60 acre forest ∙ Outdoor Finnish sauna, shower, yoga platform & hiking trails ∙ 5 min to Woodstock village, 20 min to ski Killington ∙ Spotlessly clean, tastefully furnished, well stocked with thoughtful amenities ∙2 bedrooms, 2 full baths. Lofted king master has ensuite +Lower level den w/double futon ∙ Chefs kitchen, fireplace, 2 TVs & WiFi ∙ Brookside deck w/BBQ & dining ∙Follow Falcon House on Social @falcon_house_vt

Cozy 3BR Chalet/Apt between Killington and Okemo

Cozy three bedroom apartment in the lower level of this Lindal Cedar home combines rustic charm with modern amenities to make your Vermont vacation a trip to remember! The apartment is centrally located on Route 100 between the ski and golf resorts of Killington and Okemo in the quaint village of Plymouth, Vermont. The property is set back from the road and tucked into the mountains and accessed by a bridge over the Black River. Seven recreational lakes are within a short driving distance.

Okemo Chalet + HOT TUB

Located just 5 minutes from Okemo Resort and downtown Ludlow, our cozy newly updated chalet offers stunning mountain views, a relaxing hot tub, and access to skiing, hiking, and the beautiful Lakes Region. With spacious living areas, a fully equipped new kitchen and furniture, and streaming services like Netflix and Amazon, it’s perfect for family or group getaways. Two levels of cozy couches, perfect for relaxing after a day of adventure. Killington Resort just 30 minutes to the north.

Private Mountain Sanctuary | 15 Min to Killington

*Winter Stays* Must have 4WD vehicle with snow tires or snow chains. We want you to make it safely up the mountain for those breathtaking views! This is not just a house. Welcome to your one-of-a-kind off-grid nature adventure! Wow: - Designer modern chalet on 150+ private acres - Off-grid privacy, while 15 minutes to Killington. 5 min to world class mountain bike trails. - 360 degree panoramic view - VAST trail, walking trails - Hike, Bike, Ski, Snowshoe, Stargaze, Views Views Views!

Hillcrest Manor of Vermont

One of VT’s most desired Vacation Properties! Hosted by VT’s most Reputable Hospitality Company. Unbelievable Jaw Dropping Sunrises and Breathtaking Mountain View’s! A tranquil retreat tucked in the countryside of Vermont with Rolling Hills, a Basketball/Tennis Court and Foosball table. 20min from Dartmouth + DHMC + mins from LakeFairlee & LakeMorey. Picture yourself Rejuvenating at this relaxing getaway surrounded by the pristine forests & wildlife. It’s hard for me not to live here!

Ledges Unit: Skyeship Gondola 2 miles w/ HOT TUB

The Ledges Unit is a recently updated home away from home just 2 miles from Killington’s Skyship Gondola. It is only 15 minutes from Killington’s main base area and 20 minutes to Okemo. The Ledges is a 2 story chalet in a 4 unit building. View sister listings by clicking my Host profile picture below. The 1st floor has a kitchen, living room with a large stone mantel and wood stove, dining room, and full bathroom. The 2nd floor has 4 bedrooms and bathroom.

Scandinavian design Chalet w/ private hiking trail

This bright, well-designed Scandinavian-style chalet is the perfect cozy retreat. Nestled in the woods on a plot of 20+ acres, it offers scenic views and a private hiking trail leading to beautiful vistas, transforming into a winter wonderland for skiing adventures, a summer paradise for outdoor relaxation, and a vibrant canvas for leaf peeping during Vermont's stunning fall foliage season. Goodland wood burning hot tub is available 365 days a year.