Holiday rentals in Cloak Island

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Top-rated holiday rentals in Cloak Island

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Top guest favourite
A vibrant sunset casts warm hues across the lake's surface, creating a reflective canvas of orange and pink. Silhouetted sailboats are visible in the distance, framed by the dark outline of trees along the water's edge.
Cottage in North Hero
4.98 out of 5 average rating, 43 reviews

Lake front home on private, tree-lined drive.

Enjoy the sunrise from this secluded waterfront home on a quiet, private lane in North Hero. The stunning panoramic view provides beauty in all seasons! Relax with a cup of coffee or a book on the deck and take in the sights and sounds of lake life. Take a swim in the lake or a hike at the nearby Pelots Point Nature Area. This home is a short 10 min drive into town where convenience stores, farmer’s markets and local restaurants await and just a short walk to North Hero Marina and Tiki bar!

Guest favourite
The cozy red cottage is situated on a well-maintained lawn, surrounded by blooming flowers and lush greenery. A gravel path leads to the entrance, which features a welcoming porch, while a small shed is visible in the background against a backdrop of trees.
Cottage in North Hero
4.75 out of 5 average rating, 60 reviews

Fun House w/private lake access

The Funhouse is tucked away on the secluded North Hero Island. This snug home is perfect for a small family vacation, and while the house itself is not on directly on the lake, the private family owned beach is just 400 feet away, so going for a swim is a breeze. Relax in the screened-in porch with a good book, or hang out inside on cool days using TV and WiFi, and when you get hungry, the kitchen is equipped with cookware and basic appliances to make cooking a cinch. Longer stays are available.

Top guest favourite
A serene lakeside view features an American flag gently waving in the foreground. Two rustic chairs face the water, where the sun sets, casting warm hues across the sky. Silhouetted trees frame the scene, enhancing the peaceful ambiance.
Cottage in Chazy
4.88 out of 5 average rating, 201 reviews

Chazy on the Lake

Beautiful home on a private road with A/C and strong WIFI so you can work from home. Quiet place where you can relax and watch this million dollar view all day. Chazy Boat ramp is 500 feet from the house so do not hesitate to bring your boat. You can enjoy the beautiful sunset outside or from the veranda or decide to stay cozy by the fireplace inside. Firewood is provided at the location, but you have to bring your own fire starter (NO liquid). NO DOCK! * Occupancy tax certificate 2025-0017 *

Top guest favourite
A round wooden dining table is surrounded by four green chairs, set against a backdrop of large windows that frame a snowy forest view outside. Soft natural light brightens the interior, creating a cozy ambiance.
Cabin in Cambridge
4.99 out of 5 average rating, 179 reviews

Secluded Riverside Cottage w. Sauna next to Smuggs

Welcome to our Smugglers Notch getaway at the family owned and ran Brewster River Campground! This cozy cottage sits right on the beautiful Brewster River and is immersed within 20 acres of nature tucked away in the mountains. Enjoy the river's soothing sounds as you cook, sleep, and unwind from a day of outdoor activities. Only a 3 min. drive to all of the activities at Smuggler's Notch Resort, restaurants, bars, and hiking, as well as the magical Golden Dog Farm "Golden Retriever Experience".

Top guest favourite
An aerial view captures a lush green landscape along the shoreline of Lake Champlain, featuring a blend of trees in fall colors. A spacious property is outlined by a rocky shoreline, with Adirondack chairs arranged on the grass near the water, providing a picturesque outdoor gathering spot.
Guest suite in Grand Isle
4.93 out of 5 average rating, 492 reviews

Incredible Lakefront Sunsets @ VT’s #1 Property.

Welcome to one of VT’s most beautiful lakefront property and wedding venue located in the Champlain Islands! Relax in one of many ADK chairs while enjoying incredible sunsets over Lake Champlain and the ADK Mtns. The 1 BR suite shares no space with the main home and has its own entrance and bathroom. We do have a very strict NO PET policy. The islands are accessible by road from the VT side and either bridge or ferry from NY. Please read the full description about the rental prior to booking.

Top guest favourite
A dining table is set with elegant tableware, including glassware and a decorative vase of flowers. The backdrop features a serene view of Lake Champlain, with lush greenery and distant islands under a clear blue sky.
Cabin in South Hero
4.93 out of 5 average rating, 208 reviews

Rockhaven - Island View-sauna

Rockhaven, a romantic getaway is a rare find. Step back in time and enjoy almost 600' of lake shore on Vermont's unique Lake Champlain with 180 degree views, from westerly views to New York's Adirondacks, through the north and east to Vermont's Green Mountains. This private site is 2 acres with mature trees, meadows, and wooded buffers, ensuring a peaceful and private stay. There are two cottages available; they can be rented separately or together. Each is one bedroom with private bath.

Guest favourite
A welcoming cottage exterior is depicted, featuring a spacious deck adorned with soft lighting and potted yellow flowers. Accessible ramps lead to the entrance, while comfortable seating is arranged to enjoy the surrounding nature.
Cottage in Chazy
4.93 out of 5 average rating, 27 reviews

Auntie’s Lakeside Cottage

Relax on Lake Champlain with family or friends! Our cozy two bedroom cottage can comfortably accommodate up to four people. Inside you’ll find 500 square feet of cleanliness, warmth and maritime style. A grill and new full kitchen provide the culinary options of home. A stylish bar/island compliments both kitchen and living areas. Outside you’ll find two spacious decks. One has a nautical feel, overlooking the lake, built of original stone and wood. A second larger deck overlooks the meadow.

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, 199 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. Wake up to coffee on the deck or take a stroll around the pond. And you won’t regret kicking back in the evenings - star gazing is simply magical! We are certain that you‘ll have a hard time leaving!

Top guest favourite
The exterior of the cottage is showcased, featuring a charming wooden structure with a peaked roof. Light wooden siding complements the rustic feel. A door and windows offer glimpses of the interior, surrounded by a grassy area and trees under a partially cloudy sky.
Farm stay in Fairfield
4.97 out of 5 average rating, 455 reviews

Meadow Cottage on Organic Farm with Mountain Views

The Meadow Cottage is perched on a picturesque knoll in the back of our 300 acre working dairy farm. 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, restaurants and antique stores. Or just relax at the farm, watch us milk the cows or cook up some delicious farm raised food for dinner. Well behaved dogs are welcome anytime!

Top guest favourite
An elevated cabin nestled among trees features a wooden exterior with large windows. A spacious deck is furnished with seating, providing a serene outdoor space surrounded by lush greenery.
Treehouse in Moretown
4.94 out of 5 average rating, 560 reviews

Gorgeous Treehouse High on Mountain-Amazing View!

Lilla Rustica is an elevated cabin among the trees. Private, with Stunning views this was built by "The Tree House Guys" a local Vermont company whom can be found having a season on the DIY network. Tons of detail, while keeping the design natural and simple. Unbelievable views of Camels hump State park. A loft with one queen bed and downstairs has a queen bed with three sides of the bed having windows facing the views. Hiking offered right from the cabin. An awesome getaway!

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, 312 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!

Top guest favourite
The cottage features a welcoming exterior with a sloped roof and large windows framed by neatly arranged flower beds. A stone pathway leads to the front door, surrounded by green shrubs and landscaping, set against a backdrop of trees and blue skies.
Cottage in Grand Isle
5 out of 5 average rating, 62 reviews

Island Cottage Featured in "Condé Nast Traveler"

Newly constructed centrally located charming cottage with lake views on the east shore of Grand Isle. Step out your front door and enjoy a walk, run or bike ride along the quiet scenic road that winds along Lake Champlain. Includes 5 x 7 lockable cedar storage shed with beach chairs, cooler and room for bikes and extra gear. Offering lake views only, this property is not lakefront. Free public town beach is approximately 2 miles down the road, see last 2 photos in photo tour.

Popular amenities for Cloak Island holiday rentals