Ski-in/Ski-out holiday rentals in Orleans County

Private Family Retreat, Lake Access, XC Ski-IN/OUT

Our family retreat is set on a hilltop with sweeping views of farmland, distant mountains and Caspian Lake. Inside, guests will enjoy a large open-concept kitchen and dining area, a comfy family room with a wood-burning stove, books, games, puzzles, television, sound system, and a Steinway grand piano. A 10 min. walk leads to the beautiful & private Lodge Beach, where guests will find a pristine lake with clear water, a sandy beach, boats, and a floating dock to swim to and dive from.

Ski in Ski out - fantastic location on the trail

This condo lies in the heart of the original Jay Village, offering flexible living space for a family or group of friends. With 2 bedrooms and 2 bathrooms, everyone can have the space that they need. Access via private entrance with a mud room for leaving all the outdoor gear, in summer and in winter. Enjoy free parking, outside space and a balcony with a serene view into the woods. Make the most of the resort activities (Water park, pool, golf, ice rink) for a fee to the resort.

Cozy retreat in Northeast kingdom Greensboro VT

Relax in this calm, stylish space. The guest unit (1 queen bed+a pull out couch) was built in 2023. Located on an extremely quiet rise well back from the road and overlooking Caspian Lake. Cross-country skiing right out the door. Less than 1 hour away from Stowe and Burke Mt, 10 minutes to Hill Farmstead Brewery or Barr Hill, minutes away to library, tennis, golf, art center, public beach, stores. Easy access to the trail network of Highland Lodge and Craftsbury Outdoor Center.

2 bed condo, Burke mountain vt

Listing Description Ski-in/Ski-out Burke Mountain Condo – 2BR, 1.5BA – Sleeps 4 Wake up to mountain views and step right onto the slopes! This cozy two-bedroom condo at Burke Mountain, Vermont offers direct ski-in/ski-out access in winter and instant trail access in summer — you’re right next to the world-famous Kingdom Trails and Burke Mountain’s downhill biking park. Perfect for families, couples, or small groups looking for four-season mountain adventures.

Spring Hill Farm, coffee & hot tub

Private apartment w/hot tub for 4 & abundant amenities. Kitchen stocked w/ basics for cooking. Access to back yard with grill, fire pit & pond stocked w/ trout (for feeding). Access to 1 mile +/- of scenic wooded trails & beaver pond w/ pedal boat. Close to Burke Mtn, VAST & Kingdom Trails. Hosts on site & available if needed. DISH, smart TV, movies & games. Internet & WiFi not always reliable due to rural area. NO PETS. Please don't ask.

Rustic Retreat on COC Trails/Near Hill Farmstead

This simple home is the place to go to turn off your phone, breathe, and unwind. Located down a dirt road and on our town's world class cross country ski trail system, it's a 5 min drive to the Craftsbury Outdoor Center and 15 m to Hill Farmstead/Jasper Hill Farm. Close to many places to hike, kayak, downhill ski, and more, the Airbnb is also near many local artists, breweries, and restaurants (Blackbird! Hill Farmstead!).

Northeast Kingdom/Burke Mtn: ski, bike, and swim

Stay in a beautiful, updated, two bedroom, two bathroom condo slope side at Burke Mountain. Acess to skiing, mountain biking, breweries, lakes, and hiking. Jay Peak, Lake Willoughby, and the Northeast Kingdom at your fingertips. Indoor fireplace, washer/dryer, two bedrooms, and two bathrooms. Family friendly and pets acceptable upon further discussion.

Stay at Historic Greensboro Barn

My comfortable one bedroom apt (king bed and sofa bed) tucked away inside this restored historic barn is a perfect spot for a cozy rural get away or staycation. I follow Airbnb's 5-step enhanced cleaning process. Moments away from world class food and drinks, this beautiful rural surrounding is a wonderland for many activities.

Chandler House: Picture Perfect

Chandler House provides an ideal country retreat for families and friends looking to experience the quintessential Vermont experience. The house is set up as your own 'Private Inn,' featuring four bedrooms and four and 1/2 baths in addition to comfortable Living and large eat in kitchen spaces.