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Holiday rentals in Sheffield

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Top-rated holiday rentals in Sheffield

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

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Top guest favourite
Cabin in Greensboro
4.98 out of 5 average rating, 236 reviews

Romantic NEK Log Cabin w/ Hot Tub & Fireplace

“It felt like staying at a dear friend’s cabin — one with wonderful taste who thinks of everything.” A quiet, romantic cabin for unplugging and resetting. Tucked on a wooded hillside, this romantic log cabin blends rustic soul with refined comfort. Blankets beckon, textures are rich, and every detail is intentional. Real art, fine furnishings, and luxury bedding create a feeling of quiet ease. Not just a place to stay, but a thoughtfully curated retreat you’ll want to return to year after year.

Top guest favourite
Aerial view of the property reveals a charming farm layout with multiple buildings, surrounded by lush greenery and rolling hills. The roofs feature a classic metal design, blending with the natural landscape. A winding gravel path connects the buildings, inviting exploration of the scenic surroundings.
Farm stay in Saint Johnsbury
4.99 out of 5 average rating, 119 reviews

Unique stay at a horse sanctuary

Immerse yourself in the quintessential Vermont experience at Storeybrook Farm. This rescue horse sanctuary is located amidst rolling hills, mountain vistas and a tranquil pond. "The Carriage House” is our largest suite with a fully equipped kitchen (stocked upon request), that opens up to a dining area with forest views. The living room features a woodburning fireplace and 2 built in queen bed "bunks". Enjoy sun-soaked pasture views from the main bedroom or while soaking in the clawfoot bathtub.

Top guest favourite
A modern cabin is nestled among tall trees, elevated on stilts. Large windows offer a glimpse of the interior space, featuring a minimalist design. The surrounding greenery creates a natural setting, while the pathway leading to the cabin is lined with earth tones.
Cabin in Morristown
5 out of 5 average rating, 287 reviews

Cady’s Falls Cabin

Welcome to our treehouse inspired, modern cabin overlooking The Kenfield Brook on Terrill Gorge. We are located 5 miles from Stowe and its attractions, and just a few minutes from downtown Morrrisville with all its amenities. Just upstream from the picturesque Cady’s Fall swimming hole and across the brook from the amazing Cady’s Falls bike trails, our cabin is perched atop the hillside. With its simple, minimalist design it’s easy to immerse yourselves in nature and feel at home in the trees.

Guest favourite
A modern treehouse features a warm wooden exterior, elevated on a platform among vibrant autumn foliage. Large glass windows provide a view into the inviting interior space. Steps and a small deck lead to seating arranged on the ground level, surrounded by natural scenery.
Treehouse in Newport
4.97 out of 5 average rating, 321 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.

Top guest favourite
A serene pasture is filled with various animals grazing on lush green grass. The expanse features brown and black livestock, along with sheep, peacefully interacting with the natural surroundings. Trees and a dirt road form a backdrop, contributing to the tranquil farm setting.
Farm stay in Irasburg
4.96 out of 5 average rating, 177 reviews

Private suite close to Craftsbury Outdoor Center

After a day of hiking, skiing or paddle boarding, return your home base for a quiet evening of board games. We are fairly centrally located & close to many outdoor activities & some lovely dining spots: Lake Willoughby (11 mi.); Crystal Lake (6.7 mi.) Craftsbury Outdoor Center (8.2 mi.); Jay Peak (30 mi.); Burke Mountain (31 mi.); Parker Pie Pizza (2.8 mi.); Hill Farmstead Brewery (18 mi.); andThe Manor at Runaway Pond (3.8 mi.). Other suggestions can be found under "Other details to note".

Superhost
The exterior of a spacious A-frame log cabin is presented, featuring a large porch with several wooden chairs. Expansive windows are visible, allowing natural light to illuminate the interior. The backdrop consists of lush trees and a well-maintained lawn, creating a serene environment.
Cabin in Glover
4.84 out of 5 average rating, 172 reviews

Secluded Log Cabin in the Mountains with Pond

We’re offering a comfortable, pet and kid-friendly, A-frame log cabin surrounded by 30 acres of pristine Appalachian woodland to explore and hike. We also have a 6 acre front yard complete with a 1 acre pond you are welcome to fish and relax by. After a long day enjoying all the rustic beauty and small town charm that Vermont has to offer, you can warm yourself by our pellet stove which heats both floors of our over 1,600 sq ft 4 bedroom, 2 full baths home. 6 guests max [infants included].

Top guest favourite
Large glass sliding doors open to a deck, offering expansive views of the surrounding landscape, including distant mountains. Natural light floods the interior space, highlighting the warm-toned floors and minimalist design. A small coat rack is mounted nearby for convenience.
Cabin in Burke
5 out of 5 average rating, 121 reviews

Mountain view cabin near hiking & lake Willoughby!

Welcome to your cozy retreat nestled in the heart of West Burke, Vermont! This charming tiny luxury cabin offers a serene escape with breathtaking views of Burke Mountain and its surrounding wilderness. The cabin features a well-appointed living area, perfect for unwinding after a day of outdoor adventures. Whether you're curling up with a good book by the fireplace or enjoying a cup of coffee on the deck overlooking the tranquil pond and apple orchard, relaxation comes naturally here.

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, 55 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
Tiny home in Stannard
5 out of 5 average rating, 42 reviews

Boreal Camp & Sauna

Welcome to Boreal Camp, a minimalist tiny home & sauna nestled in the forest. A place of ultimate privacy, perfect for a writer's retreat or a couple's getaway. Sanctuary may look like savoring a wood fired sauna then rinsing off under the Big Dipper, laying in a hammock by the stream and starting a new book, or listening to your favorite album over and over again. Minimalism is our north star. As the world gets busier we invite you to take life at a slower pace...bienvenue!

Top guest favourite
A historic red schoolhouse stands amidst green trees, featuring a front porch adorned with hanging flower baskets. The structure showcases a classic bell tower on the roof and large windows that invite natural light. A grassy area surrounds the building, enhancing its serene setting.
Home in Craftsbury
4.97 out of 5 average rating, 226 reviews

Ann’s Schoolhouse

Ann’s Schoolhouse is a beautiful Historic Schoolhouse built in 1901 and nestled in the green mountains of Vermont. Complete with the original school bell, chalk board and desks from 1901 you'll take a trip back in time when you visit! You and your family will love the quiet serenity as you sit by the fire pit and take in the views. This cozy home is perfect for your family vacation or event, couples weekend away or a friends trip. You'll love calling Ann's Schoolhouse home!

Top guest favourite
A yellow and white daffodil blooms prominently in the foreground, surrounded by lush green grass. In the background, a rustic red barn with the sign 'Spring Hill Farm' is visible against a cloudy sky.
Flat in Sutton
4.99 out of 5 average rating, 510 reviews

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.

Top guest favourite
A rustic cabin is surrounded by lush greenery in a serene woodland setting. A designated fire pit, framed by smooth stones, is accompanied by two folding chairs and a picnic table, inviting outdoor gatherings and relaxation.
Cabin in Sheffield
4.98 out of 5 average rating, 47 reviews

Sugarwoods Cabin

Enjoy hearing the birds in the trees around the cabin site. You have the solitude of the woods with no close road or neighbors! Take it easy being unplugged and relaxed in this quiet spot. Battery lights provide a cozy atmosphere as the cabin is off grid. Plenty of wood for campfires. 5 gal water provided. You need to hike up about 400 feet. Located half mile on dirt road from VASA trail and 14 miles from Kingdom Trails (biking) in East Burke.

Popular amenities for Sheffield holiday rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Caledonia County
  5. Sheffield