Holiday rentals in Orleans County

Tester's Haven Cottage, Lake Parker

This is a classic Vermont SEASONAL ( June- Oct) early 1950s cabin or cottage that is right on the water facing the West. One side sits next to a dirt road that is pretty quiet. Some cars, farm machinery & four-wheelers do go by. However, you can sit facing the water and feel like you have left the rest of the world behind as you listen to the loons. This special kind of space is for those who like a touch of country, it is not a hotel, it is not a party place, but a lovely RUSTIC cottage/cabin.

Location · Family · Grill

Bunkhouse on Caspian Lake

Take a break and unwind at our rural cottage on the lake. Equipped with full kitchen and bath, main bedroom with a king bed and 2 additional bedrooms with full beds. The house is situated on a hill with kayaks available for use. Enjoy miles of hiking trails at the Nature Conservancy's 256-acre Barr Hill Preserve, or biking on the extensive Lamoille Valley Rail Trail. Greensboro has an historic general store (Willey's) and the award-winning brewery, Hill Farmstead, is nearby in Greensboro Bend.

Family · Value · Wifi

Secluded Luxury Treehouse - Hot Tub + Projector

Our treehouse is a haven of well-being, peace, and elegance. In our stunning modern treehouse we have brought relaxation to a whole new level. Surrounded amongst us is nothing but woods & wildlife. An experience not to be missed. Put your favorite movie on the projector, get Zen in the cozy sun room, jam out to music on the record player, or grab a towel, and head for the custom cedar hot tub. It is time to create core memories that will never be forgotten. Welcome to a little slice of heaven.

Family · Location · Comfort

Pristine Lake Location in Vermont

Our cottage is located on Lake Memphremagog, an international lake shared with Canada. Visit our nearby hobby farm/children’s museum. Kayak, bike or hike to stunning natural settings or take day trips to a variety of interesting destinations, including maple sugar shops, alpaca or dairy farms, golf courses, a ski resort with indoor waterpark; or cross the Canadian border a few miles away and explore Quebec. A boat dock is available for use at our cottage with an access ramp a 1/4 mile away.

Value · Location · River

Jay Peak Retreat

The Jay Peak Retreat, Experience the Northeast Kingdom’s premier destination at Jay Resort, known for record snowfall and Vermont’s largest indoor waterpark. This stylish cabin offers an open-concept layout perfect for cozy gatherings and après-ski. Blending upscale comfort with rustic charm, enjoy a creek out back, river across the street, fire pit, and plush outdoor chairs. 1 hour from Burlington, 2 from Montreal, 35 minutes to Sutton Quebec!! Long Trail hiking entrance close to the cabin.

Family · Location · Outdoor spaces

VT Lakeside getaway on beautiful Crystal Lake.

In the heart of the Northeast Kingdom, Lakeview House is located on one of Vermont's cleanest & most beautiful lakes, Crystal Lake! Swim! Boat! Fish! Enjoy a private dock, fire pit, gas grill, pool table & more. 200 feet of private waterfront just across the street. You can hit the water with a stone from the front deck. Use the kayaks & canoe! Nearby golf, hiking, Kingdom Trails, ski areas, snowmobile & snowshoe trails. A short drive to Hill Farmstead Brewery for best beers in the world!

Value · Location · Pool

Luxury Waterfront Loft · Kayaks, Firepit & Dock

Amazing 2-bedroom lakefront loft, located directly on the American side of beautiful International Lake Memphrémagog. From swimming to the gorgeous fall colours hikes, skiing and ice-fishing, the loft is a great, quiet spot to relax or enjoy outdoor activities all year round. Located 10-min from Newport, VT with a variety of restaurants and 30-min from Jay Peak (USA) & Owl's Head (Canada) where you can golf, ski and hike! Only a 2-hour drive from Montreal and 3.5 hour drive from Boston!

Family · Location · View

A Magical Mountainside Farm: Your Personal Narnia

Nestled deep in the woods of the Northeast Kingdom, Mossflower Hill Farmstead is an idyllic home with stunning mountain views. The house is at once spacious and cozy with a blend of historic Vermont architecture and clean Scandinavian design. Spend the mornings watching the sunrise from the sofa, deck, or sauna. Cook and eat indoors or outdoors. Head to Craftsbury Outdoor Center, Burke, Jay Peak, Stowe, or nearby lakes. Reconnect with nature in one of the NEK's most stunning properties.

Location · Family · Cleanliness

Private 117-Acre Estate | Fall Views + Fireplace

Escape to Vermont’s Northeast Kingdom in this secluded post-and-beam retreat with sweeping mountain and valley views. With room for up to 8 guests, it’s an ideal home base for family trips, ski weekends, hiking, biking and year-round Vermont adventures. Relax by the wood-burning fireplace, unwind in the steam shower or jetted soaking tub, and enjoy peaceful outdoor spaces—all within easy reach of Craftsbury Outdoor Center, Hill Farmstead Brewery, lakes, trails and four ski resorts.

Family · Indoor spaces · View

Balance Farm: Modern Cabin near Jay Peak

Escape to a tiny luxury cabin nestled in the peaceful woods of Irasburg, Vermont. Surrounded by towering trees and the sounds of nature, this secluded retreat is perfect for relaxation and adventure. Explore scenic trails just beyond your door, then settle in for a night of stargazing from bed. Thoughtfully designed with modern comfort and rustic charm, the cabin features a cozy sleeping space, a well-appointed kitchenette, and everything you need for a peaceful escape.

Value · Location · Bathroom

Daniels Pond Waterfront Cottage – Northern VT

Relax at this pondfront cottage on Daniels Pond in Northern Vermont, tucked away on quiet dirt road. Enjoy direct waterfront access, peaceful views, and a cozy retreat perfect for friends, families, or small groups. Daniels Pond offers a rare sense of tranquility with pristine, quiet waters (no large motors or jet skis permitted) and a limited collection of ~20 waterfront cottages. This private Vermont cottage offers the perfect blend of comfort, nature, and solitude.

Family · Comfort · View

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 should be strong we now have fiber. Poor cell service. NO PETS. Please don't ask.

Location · Family · Quiet