Holiday rentals in Sheldon

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Top-rated holiday rentals in Sheldon

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A serene outdoor space features a patio table surrounded by chairs, set against the calm waters of Metcalf Pond. A large umbrella provides shade, while an American flag gently flutters nearby. The backdrop includes rolling hills adorned with autumn colors.
Cottage in Fletcher
4.99 out of 5 average rating, 190 reviews

Metcalf Pond Camp Convenient to Smugglers Notch

Handcrafted cozy waterfront camp on Metcalf pond. Propane fireplace provides for welcome warmth after fall or winter adventures. Soak in the Hot tub on the deck. Custom spiral staircase accesses carpeted sleeping loft with books, TV, rocking chair. Enjoy the quiet off season brings to the area when most camps are shuttered for winter. Enjoy staying in and cooking and taking in the cozy atmosphere or make the approximately 20 minute drive to Smugglers Notch or enjoy other local attractions.

Guest favourite
Treehouse in Newport
4.97 out of 5 average rating, 317 reviews

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.

Guest favourite
Home in Fairfield
5 out of 5 average rating, 8 reviews

Sugar House Homestead: A Perfect Retreat

Escape to Sugar House Homestead—a cozy 3-bedroom getaway perfect for couples, families, and outdoor enthusiasts. Just 30-45 minutes to All points of Lake Champlain, so easy access for fishing. Explore scenic back roads and nearby wedding venues like Swiss & Bloom, Jenny’s Barn, Soule House or Jay Peak Resort. Sleeps 8, with a full kitchen, washer/dryer, Smart TV. Watch deer from the deck and unwind in peaceful, natural surroundings. For work crews or fishermen , plenty of room for trailers.

Guest favourite
A serene landscape shows several Jersey cows grazing on lush green grass near a pond. The water reflects the blue sky and distant mountains, while the surrounding trees add depth to the tranquil rural setting.
Farm stay in Fairfield
4.98 out of 5 average rating, 328 reviews

Organic Farm Hideaway Home and Pond

The house is tucked into the back of our 300-acre working dairy farm and offers breathtaking views of Mt. Mansfield. We are located in between two of Vermont's best ski resorts, Jay Peak and Smuggler Notch. Come for a winter adventure full of downhill skiing, riding or x-country touring. Stay for the local breweries, distilleries and restaurants. Or just relax at the farm, cozy up by the wood stove and cook up some delicious farm raised food for dinner. Well behaved dogs are welcome anytime!

Guest favourite
A spacious home is set against a backdrop of vibrant autumn foliage in shades of red, orange, and yellow. The building features a large deck that wraps around, providing an expansive view of the surrounding landscape. A grassy lawn extends toward the house.
Home in Berkshire
4.95 out of 5 average rating, 21 reviews

Cozy Vermont Home Near Jay Peak & Wedding Venues

Enjoy stunning sunrises over Jay Peak from this 3BR, 2BA home in Berkshire, VT. This spacious home offers a large deck with mountain views and modern, cozy comforts. Just 25 mi. to Jay Peak Ski Resort and nearby wedding venues Swiss & Bloom, Berkshire Barn & Gardens and The Abbey. Only 5 miles to Canada—perfect for day trips to Montreal. Enjoy nearby golf courses, wineries, State parks, scenic bike trails, hiking and local breweries. A perfect year-round Vermont getaway for groups & couples!

Top guest favourite
Flat in Fairfield
5 out of 5 average rating, 19 reviews

The Nest: Cozy Garage Loft with Sauna

Welcome to the Nest- a private one-bedroom loft apartment above a converted garage, set in scenic rural Vermont. The space includes a full kitchen and elevated views of the surrounding countryside. Guests enjoy shared access to a sauna, exercise equipment , firepit, and gas BBQ, along with hiking and cross-country ski trails on the property. A peaceful retreat just 35 minutes from Smugglers’ Notch, 25 minutes to Lake Champlain, 40 minutes to Burlington, and 1.5 hours from downtown Montréal.

Top guest favourite
Home in Richford
4.99 out of 5 average rating, 159 reviews

Peaceful + Cozy Farmhouse Near Jay Peak + Sutton

Our guest farmhouse, located 1 mile from the Canadian border, is close to Jay Peak Ski Resort and Mount Sutton. Mountain and meadow views are spectacular from every window! Here, you are perfectly poised to explore both the quaint, foodie-focused, French-Canadian, Eastern Townships, just across the border in Quebec AND the scenic back-roads, abundant lakes, family farms, mountain trails, local pubs, and old general stores of Northern Vermont. Or just enjoy the porch & peaceful atmosphere!

Top guest favourite
A guest cabin nestled in the woods is visible, featuring a spacious green yard and a flowing brook nearby. A hammock hangs between trees, while red outdoor chairs are arranged around a stone fire pit. The cabin's elevated deck overlooks the serene landscape.
Guest house in Montgomery Center
4.97 out of 5 average rating, 403 reviews

Cabin in the Woods VT - Discount Jay Peak Lift Tix

Come enjoy the ski season and a relaxing weekend at our private guest cabin in the woods. A brook flows through the backyard, providing a peaceful natural backdrop and a stone outdoor fire pit for great campfire fun. The main floor bedroom has 1 queen bed and the loft has 1 queen and 1 twin. There is also a living room couch. Just 5 min to town, 15-20min to Jay Peak! Use our vouchers for discount lift tickets! **We recently added “The Loft” listing on the other side of the same property**

Top guest favourite
A spacious cabin is set in a lush green landscape, surrounded by tall trees. Large windows dominate the front, allowing natural light to fill the interior. The sloped grassy yard leads to a relaxing outdoor space, perfect for enjoying the serene woodland views.
Cabin in Enosburg
4.99 out of 5 average rating, 197 reviews

The Rustic Retreat at Twin Ponds

Take it easy and make yourself right at home in our woodsy cabin tucked away in the Cold Hollow Mountains. As you head down the drive, let your worries fade away - you’re now on cabin time. Relax in the clawfoot tub after a day of travel or prepare a home-cooked meal in the well equipped kitchen. When morning comes, enjoy your coffee while cozied up in front of the fireplace or stay in bed and take in the views. And with plenty of woods to explore, it's your perfect escape at your pace.

Top guest favourite
Two unique chalet structures, designed with a modern aesthetic, are situated on a sloped landscape. The buildings feature angular shapes and large glass windows, which reflect the surrounding forest, inviting nature indoors. The ground is covered with natural foliage and rocks.
Chalet in West Bolton
4.99 out of 5 average rating, 236 reviews

The Binocular: Peaceful Architect Cottage

Cosy timeless chalet conceptualized by the architects of _naturehumaine. Nestled into the cliffside at an altitude of 490 meters (1600 feet), its unique design is distinguished by boldness and originality and fits with harmony in its environment. Surrounded by forest, the cottage offers breathtaking views of Mount Glen and the surrounding nature largely protected by the Appalachian Corridor. The perfect silent place to relax and unwind. Photo: Adrien Williams / S.A. CITQ #302449

Top guest favourite
A modern cabin design is depicted, featuring large glass windows that reflect the surrounding trees and sky. The geometric structure showcases a pointed roof and an inviting entrance, blending into the natural landscape. A glimpse of the interior reveals a cozy sleeping area.
Tiny home in Irasburg
4.98 out of 5 average rating, 53 reviews

Balance Farm: Modern Cabin near Jay Peak

Escape to this tiny luxury cabin nestled in the peaceful woods of Irasburg, Vermont. Surrounded by towering trees and the sounds of nature, this secluded retreat offers a perfect getaway for relaxation and adventure. Enjoy the scenic trails just outside your door or stargaze from your bed. Thoughtfully designed with modern amenities and rustic charm, the cabin features a cozy sleeping space, a well-appointed kitchenette, and everything needed for a peaceful retreat in the woods.

Top guest favourite
A small vase containing vibrant flowers is placed on a wooden shelf. Sunlight filters through large windows, illuminating a loft area with a wooden ceiling. Spacious seating areas are visible below, providing a welcoming atmosphere.
Barn in Westford
5 out of 5 average rating, 309 reviews

The Book Barn: Newly Renovated Guesthouse

Enjoy all Vermont has to offer in this bright, airy space minutes away from Burlington and the mountains. On 14 acres with a brook, it’s a short walk down a dirt road to a historic covered bridge and town common. Fall colors are breathtaking when taken in from the barn deck, while Spring and Summer visitors enjoy free concerts on the town green on Sundays. Spectacular sunsets and hot air balloons are familiar sights. It doesn’t get much more Vermonty. *Note: No Cleaning Fee!

Popular amenities for Sheldon holiday rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Franklin County
  5. Sheldon