Cottage holiday rentals in Orleans County

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Top-rated cottage rentals in Orleans County

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Top guest favourite
A charming guest house is set against a backdrop of lush greenery and vibrant flower beds. Brightly colored irises and tulips bloom in the foreground, while the dark wooden exterior of the house contrasts with the surrounding nature. A gravel pathway leads to the entrance.
Cottage in Craftsbury
4.98 out of 5 average rating, 55 reviews

Adorable 3 Bed Room guest house fireplace & Fiber

Get away to a cozy VT back road guest house surrounded by nature. Walk, ski or bike the quiet dirt road, hike or snowshoe on property trails available right from your door, enjoy laying in the hammock by the pond or spend the night in the pond house listening to the natural sounds and watching the stars. Every season is special with fall foliage, winter activities, summer concerts on the common and lakes nearby for fishing, swimming or paddling. Many interesting possible day trips await you.

Guest favourite
A spacious outdoor seating area features a weathered wood deck surrounded by vibrant autumn trees. A large umbrella provides shade over a rectangular table, complemented by a comfortable sectional sofa with soft cushions, inviting relaxation while overlooking the serene lake.
Cottage in Newport
4.87 out of 5 average rating, 174 reviews

Lakefront Cabin | Boat Dock-Fireplace-Sunset Views

Nestled in the Rolling Hills of rural Vermont, our Pet Friendly 3BR/2.5BA Lake House has Tasteful Furnishings, Modern Conveniences, and an airy, open design. Enjoy your stay swimming, boating, or fishing on the lake in the summer or exploring the rich history of downtown Newport (15 min drive) and skiing at nearby Jay Peak (30 min drive) in the winter. You will be welcomed with Luxury White Bedding, a Fully Equipped Kitchen, a Beautiful Private Lake Front Dock, and all the Comforts of Home :-)

Top guest favourite
A wooden boat dock extends over calm waters, with a boat moored alongside. Lush green grass and vibrant orange flowers frame the scene, providing a natural border to the water's edge.
Cottage in Newport
4.89 out of 5 average rating, 180 reviews

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.

Guest favourite
The charming exterior of the Sugar Shack is showcased, featuring rustic wooden siding and large windows adorned with planters. A covered porch invites relaxation, while a fresh layer of snow blankets the ground and surrounding trees, highlighting a peaceful winter setting.
Cottage in Montgomery
4.96 out of 5 average rating, 120 reviews

Crofter's Green @ Jay Peak: Sugar Shack

The Sugar Shack is one of five micro-cottages at Crofter's Green nested on twenty-five beautiful acres of land just 7 minutes from Jay Peak Ski Resort and 5 minutes from the warm, eclectic town of Montgomery Center, Vermont. Whether you're looking for a relaxing escape from the hustle and bustle, or want a cozy home-base from which to ski, hike, shop, or explore the nearby cities of Montreal and Burlington, the Sugar Shack is your ideal destination. Find us on social media! @croftersgreen

Guest favourite
The front exterior of a historical cottage is framed by lush green trees and blooming lilac bushes, providing a vibrant contrast against the structure. A small porch is visible, offering a view of the surrounding nature.
Cottage in Westfield
4.9 out of 5 average rating, 177 reviews

Historic Schoolhouse Minutes From Jay Peak

After a long day of hiking, biking, or skiing, come take a swing at our charming historical cottage. Dating back to the mid 1800s it was one of the first schoolhouses in the area, today it is filled with all the modern luxuries one would need. Our quaint porch is perfect for bird watching or leaf peeping. The inside includes high ceilings, a bedroom and a cozy loft- both with queen beds. French culture is only a 10 min drive away; Vermont culture is abound with maple syrup and warm locals.

Top guest favourite
A private dock extends over the tranquil waters, featuring two Adirondack chairs positioned under an umbrella. The surrounding landscape consists of lush greenery and nearby homes, providing a serene setting for relaxation.
Cottage in Derby
4.98 out of 5 average rating, 60 reviews

On Golden Lake Salem

Welcome to our lakefront ranch style home in northern Vermont (a leaf peeper’s dream)! Located on a quaint and quiet street - you will have your own dock, beach, boats, and yard - all the ingredients you need for a fantastic vacation. In case of rain you will be all hooked up with books, board games, and Netflix, Amazon prime, HBO Max, Hulu, etc. Year round fun - as we are right on the snowmobile trail! We are honored to host you knowing that you will make the best memories in our space!

Top guest favourite
The cottage is positioned along the lake, featuring large windows that overlook the water. A grassy area with several lounge chairs is located nearby, inviting relaxation. A stone path leads to the water's edge, framed by leafy trees providing shade.
Cottage in Newport
4.97 out of 5 average rating, 59 reviews

Cozy yet roomy cottage right on Lake Memphremagog!

WELCOME TO THE CAL ZONE! Lake Memphremagog is a special place located on the border of Canada with half the lake in the US and half in Canada (31.6 miles long). The views of the lake and the mountains never get old. We get the best sunsets too. The cottage is cozy but also roomy and is steps away from the lake. It offers all the creature comforts of home while roomy, open and one level. The lake is shallow, clear and has a sandy bottom. The yard is large and available for family fun too.

Top guest favourite
A blue cottage is surrounded by a snow-covered landscape, with a sloped roof and multiple windows. Snowy trees are visible in the background, and a path leads to the front door, which is framed by a small overhang.
Cottage in Burke
4.97 out of 5 average rating, 66 reviews

East Burke Cozy Cottage mins to skiing at Burke Mt

Cozy one-bedroom cottage with stunning views close to all the Northeast Kingdom has to offer. Ride your bike right off the property onto the Kingdom Trails, grab your skis and find yourself at Burke Mountain in less than 5 mins and take a short drive to gorgeous Lake Willoughby for all your water sports adventures. You can also explore the cottage's 30 acres of woodlands and streams. This thoughtfully furnished rustic cottage has everything you need to enjoy the Northeast Kingdom!

Top guest favourite
A charming wooden cabin sits elevated beside a calm lake, surrounded by lush greenery. The exterior features large windows and a patio with steps leading to the water's edge. The landscape includes well-maintained grass and hints of garden beds.
Cottage in Newport
4.96 out of 5 average rating, 68 reviews

Vermont Waterfront Cottage

SmartHome, Wi-Fi, yard robot, A/C, Heat, Echo, Music, Fans, Bidet, In-Wall USP outlets.. Dock w/swim ladder, Umbrella, sandy beach. bench & lounge-sun chairs. Berries(in season) Canoe available, bring your water toys, boating, tubing but no jetski's. VAST-trails w/i 1/2 mile. Best outdoor fun for gathering with the family at the huge custom stone fire-pit surrounded by boulders for natural seating. Horseshoes & croquet on lawn. Ski resorts, cruises, plane rides, festivals. More!

Guest favourite
A cozy living area showcases wooden walls and a shiny floor with splattered paint patterns. A red sofa and a comfortable chair provide seating. Nearby, a digital player piano and a small side table are visible. Natural light filters through large windows, creating a welcoming space.
Cottage in Westmore
4.92 out of 5 average rating, 61 reviews

Lake Willoughby Mill Brook Studio cottage.

Walk to Lk Willoughby, this newly converted wheelchair accessible Studio cottage has it all for short or long term visits. Queen Tempurpedic, Serta single pullout. Digital Yamaha Player Piano. Bring your old Vinyl! Oldtime record player. Vintage typewriter for your crafty pleasure. If the lake beach is crowded, explore the brook with falls. Stone chairs in the landscape to enjoy the sights and sounds of the brook falls, and RELAX. Firepit. Well behaved pets are most welcome.

Top guest favourite
A view of colorful tulips and green foliage frames the cottage's side, with a serene lake visible in the background. Soft hills rise beyond the water, surrounded by lush trees, under a cloudy sky.
Cottage in Glover
4.97 out of 5 average rating, 73 reviews

Relaxing cottage retreat on Shadow Lake Glover VT

Enjoy a peaceful escape in this sweet little newly renovated and stylishly minimalist cottage with stunning water views and private beach access on beautiful Shadow Lake. An ideal space for a solo writer's retreat, a romantic weekend, or a family getaway. In the evening, stargazing from the secluded back deck is absolutely mesmerizing and in the morning, it's the perfect spot to savor a quiet cup of coffee. In the winter enjoy the cottage’s coziness after a day of skiing!

Top guest favourite
A tire swing hangs from a tree branch, silhouetted against a serene lakeside scene at twilight. The calm water reflects the soft colors of the sunset, with gentle hills in the background. Clouds float softly in the evening sky above.
Cottage in Derby
4.99 out of 5 average rating, 71 reviews

Lakeside Cottage in Derby

Cute southern exposure cottage with a great view of the lake, and lots of light. Sandy beach for fun in the sun, and a fire pit for those cool evenings. 40 mins to world class mountain biking (kingdom trails), and 40 minute drive to ski resorts Burke and Jay Peak. Also the cottage is a 5 minute walk to the "Kingdom Petsafe dog park". Great place to get away from it all, yet still near amenities.

Popular amenities for cottage rentals in Orleans County

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