Holiday rentals with a fireplace in Windsor County

Cozy - Killington 40 min. Woodstock-Hanover-Piano!

Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental

Private, 1 bedroom boutique tiny home

This boutique tiny home is situated in the picturesque Upper Valley of Vermont. The nearly 50 acres of private land is equal parts woods and water. You will wake to the mooing of dairy cows. Have your coffee on the porch while watching birds dive for their breakfast on the pond. Inside you will find every modern amenity. A fully appointed chef's kitchen. A living area filled with comfy furnishings and a cozy fireplace. Upstairs is a queen bedroom with an ensuite double showered bathroom. Heaven!

The Barnbrook House

Come relax in the serenity of the quiet countryside. This home boasts beautiful views, a large stone fireplace, and stained glass windows throughout the home. Enjoy the comforts of home with a full kitchen, amenities, and beds with 1500 thread count sheets while exploring the interesting features of this one of a kind house. Sit by the spring fed pond overlooking the property laced with apple trees. The home has direct access to short walking trails and is close to VAST trails for snowmobiling.

Adorable one bedroom studio in 1844 farmhouse.

Keep it simple at this peaceful and centrally-located place. We have a beautiful 1844 farm house located in Quechee, that has been in our family for over a hundred years. It is located less than a 1/4 mile from the Quechee Gorge and Antique Mall. The farm includes fifty acres of land and trails with wonderful views of Mt. Ascutney, Killington and more. We also abut the state park which has twelve hundred acres of land. All perfect for hiking, snowshoeing, snowshoeing, biking or just relaxing.

~The ClubHaus~

Appreciate life at our peaceful home away from home in the Vermont Woods... Located a short drive from Killington and Okemo ski mountains, The ClubHaus is the perfect spot to unwind after enjoying four season New England activities. Breweries and great food are nearby in Woodstock, Manchester, and Dorset. Huge fireplace, hot tub, comfortable beds, and lots of thoughtful touches provided to welcome you to the ClubHaus family. Wifi, Netflix, and Disney+ included, no cable. @clubhausvt on IG

Jack S'Bearo - Slopes, Fireplace, Pool.

Ahoy, ski enthusiasts! "Jack S'Bearo" - a renovated 1-bed, 1-bath on Pico Mountain, VT, offers an exhilarating ski experience steps from the lift and a shuttle to Killington Resort. The new kitchen, wood-burning fireplace, and balcony make it a haven for relaxation. This ski on/ski off treasure boasts a cool design for easy access to the slopes. Grab your gear from the ski locker, step outside, and set sail to the lifts. Make "Jack S'Bearo" your pirate's cove, where adventure meets comfort!

Elegant Alpine Condo

Newly renovated 1-bedroom Whiffletree condo with an upscale alpine feel—just minutes from the slopes, access road, and snow tubing. Fully stocked with essentials and includes a ski locker for your gear. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). Sleeps up to 4 with a king bed and queen pullout sofa. Baby Pack & Play crib, mattress and sheets available upon request for $50 per stay. Killington Reg #007718

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". A lofted space on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony. For more go to @theloft.vt

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

Escape in a beautiful light-filled upscale cabin deep in the woods at Sugar Maple Mountain Retreat. Relax at the end of the day in our hot tub which is shared between our 3 cabins. Steps away from two picturesque lakes, enjoy complimentary seasonal use of our kayaks, paddle boards and snow shoes. Go fishing, biking, hike country roads or trails on the 1275 acres of surrounding preserved land. In winter hop on the VAST trail nearby. 4 WD Required Dec 1- April 15th

Yurt In The Woods - Come to the Yurt.

The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. October 6th and 12th are currently vacant if you want a fall foliage trip. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October