Holiday rentals in Chelsea

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Top-rated holiday rentals in Chelsea

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

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Top guest favourite
A charming wooden cabin is surrounded by lush greenery, with a sloped roof covered in red metal. Large windows provide ample natural light, while a gravel path leads to the entrance, inviting guests to explore the serene rural setting.
Tiny home in West Fairlee
4.96 out of 5 average rating, 188 reviews

Off Grid Tiny House

This sweet little house is great for those who want to get away from it all. It's like camping but with many more creature comforts. The house has hot and cold water in the summer but is off for the season now, end of October. The house does not come with sheets and towels but if you need that, please let me know and I’ll make that happen for a small fee ($15)! Great for kids! Mountain biking and hiking locally and right out your door. 10% veteran discount. Spectacular and cozy in the winter.

Top guest favourite
A spacious log cabin is shown with a green metal roof and multiple windows. A wraparound deck and balcony are visible, surrounded by grassy areas and trees. The cabin's rustic charm is complemented by the natural landscape, offering a serene and inviting atmosphere.
Cabin in Corinth
4.99 out of 5 average rating, 249 reviews

Skip's Place

Skip's Place is the epitome of privacy and beauty. Modern amenities in a Vermont log cabin on 60+acres that anyone could enjoy. Master bedroom has king-bed and bath with jacuzzi tub. Downstairs includes a spacious dining room with full kitchen, a second bathroom and two bedrooms each with a full-sized bed. Easy access WiFi and two flat screen TVs with DVD players and movie collection for rainy afternoons. Outdoor fire pit, hiking trails, and fish pond guarantee a unique, peaceful experience.

Guest favourite
A secluded cabin is nestled among snow-covered trees, showcasing a timber exterior and large windows that reflect the winter landscape. An inviting deck extends from the cabin, surrounded by a tranquil blanket of snow, creating a serene atmosphere.
Cabin in Roxbury
4.97 out of 5 average rating, 270 reviews

Off Grid Secluded Cabin on 37 Acre Farm

In a secluded, hand-crafted off the grid cabin, come and enjoy the elements with us at Drift Farmstead. A 3-minute walk leads you through gardens and pasture, to Ravenwood, a small, intimate cabin with everything you need. Be it an extended weekend tucked in seclusion, amongst the birds, river and trees, or find the comforts of a 37 acre small farm nestled in the mountains and settle in, working from afar. Top shelf skiing at Sugarbush is near, along with Vermont's finest grub and beer.

Top guest favourite
A warm wooden cabin is set against an autumn backdrop, with vibrant orange and yellow foliage surrounding it. Steps lead to a pair of French doors, inviting guests inside, while a smaller structure sits nearby, complementing the serene natural setting.
Farm stay in Topsham
4.98 out of 5 average rating, 390 reviews

Fairytale cabin at The Wild Farm

Lay in bed and look out the huge picture window at the farm. You might see cats climbing trees, hummingbirds, snowflakes falling, lightning storms and many more beautiful moments. We have a Wolf, don't be alarmed she is as friendly as can be and will greet you and escort you to the cabin. If you like nature, animals, walking in the forest, cuddling up by the wood stove, then this is the place for you. The cabin is surrounded by gorgeous perennial gardens. We look forward to hosting you!

Top guest favourite
A vibrant garden features an array of yellow daffodils and blooming flowers, extending towards the grassy area. In the background, a charming cottage with a brown roof is nestled among lush trees under a clear blue sky, creating a serene country setting.
Cottage in Tunbridge
4.97 out of 5 average rating, 111 reviews

Vermont Hillside Garden Cottage

Cozy converted artists’ studio, tucked in the hills at the end of a country road. Open the French door to views of a sprawling garden and rolling fields, alight with fireflies in the spring and bursting with color in the fall. Warm yourself by the wood burning stove after winter fun or unwind with a local microbrew by the fire pit, listening to the Whippoorwills on a summer evening. Beautiful in all seasons, this modern, comfy cottage is the perfect place to get away from it all.

Guest favourite
The exterior of a historic farmhouse features a blend of brick and white siding. The structure is surrounded by green grass and mature trees. A private entrance is visible, along with a seating area with chairs. The roof showcases a modern metal design, enhancing the traditional architecture.
Flat in Randolph
4.98 out of 5 average rating, 224 reviews

Historic Wayside Farm - a working dairy farm

Located on a historic certified organic dairy farm, this lovely apartment offers guests a cozy retreat with one comfortable bedroom and a clean, well-kept bathroom. Whether you’re relaxing after a day of exploring or enjoying a quiet morning coffee, this marvelous spot provides a peaceful atmosphere. We are centrally located, just a short drive away from area ski resorts, hiking trails, mountain bike networks, breweries and more. We hope you'll enjoy your stay at our apartment.

Top guest favourite
A cozy living area is highlighted by warm wood paneling and large windows allowing natural light. A stylish record player is placed on a small table near a comfortable seating arrangement featuring a light sofa and wicker chairs. A decorative rug and a small stove add to the inviting ambiance.
Cabin in Roxbury
4.98 out of 5 average rating, 191 reviews

Cozy cabin retreat

This is the cozy, romantic cottage you've been dreaming of! Fall asleep to the sound of the stream outside the window. Enjoy sledding, snowshoeing, or XC skiing around the meadow, or use this as a convenient base for all your Vermont adventures. Nestled in a hidden valley in the center of Vermont, the cottage is conveniently located a short drive from many ski areas, award-winning Montpelier and Randolph restaurants, the bustle of the Mad River Valley and I-89.

Top guest favourite
The cabin features a wooden deck with steps leading to the front door, surrounded by lush green grass and a variety of colorful foliage in the background. Potted plants are positioned near the entrance, enhancing the natural setting.
Cabin in Vershire
5 out of 5 average rating, 260 reviews

Comfortable cozy cabin in the hills of Vermont!

Lovely cabin situated in a small clearing in the hills of Vermont. All appliances, fully equipped kitchen, washer and dryer. No TV, but strong WiFi for streaming on your own device. We have approximately 20 private acres of hiking trails, ponds, streams, and woods. 15 miles from Lake Fairlee, 26 miles from Dartmouth College, 44 miles from Woodstock VT. Our home is next door, about 40 yards away through a grove of trees. Not suitable for children or pets, sorry.

Guest favourite
The exterior of a rustic red cabin is shown, featuring a sloped metal roof and a stone chimney. Two white chairs are placed near the front door, and a small white storage shed is visible on the side. Lush greenery surrounds the structure.
Tiny home in Chelsea
4.9 out of 5 average rating, 141 reviews

Windswept Acres Sugarhouse

Looking for a Rustic adventure? ...the Sugar House is your stop. Well water no longer comes via a hand pump (we just added running hot and cold water!) but there is still an outhouse in the back. A favorite of many of our "regulars" with a great view of the sunrise. You are on 55 acres with two ponds for swimming, fishing, and paddling, plenty of hilltops to hike to and soak in panoramic views... and plenty of privacy.

Top guest favourite
An expansive view of rolling hills showcases a vibrant tapestry of colorful autumn foliage. The serene landscape reveals a distant farm with several buildings nestled among the trees, set against a backdrop of mountains under a clear blue sky.
Guest suite in Royalton
4.96 out of 5 average rating, 286 reviews

Private Guest Suite on 155 Acre Royalton Town Farm

1 Bed, 1 Bath apartment attached to historic farm house. This cozy space is the perfect spot for a weekend getaway or a long family vacation on a historic Vermont Farm. Equipped with all the linens and dishes you will need. Close to I-89 and 30 minutes of Ski Resorts like Saskadena Six. Property of 155 acres has trails, sledding hills and our farm animals you can enjoy. Check our reviews, you won't be disappointed!

Top guest favourite
The kitchen area features a central island with seating, surrounded by dark cabinetry and stainless-steel appliances. Exposed wooden beams and a sloped ceiling create an airy atmosphere. A dining area is visible in the background, adorned with a wooden table and comfortable chairs.
Loft in Randolph
4.95 out of 5 average rating, 113 reviews

Stylish factory-farmhouse deluxe loft

Welcome to our historic, newly renovated loft-style home. 3,ooo square feet of peace and quiet, it spreads out the entire 2nd floor of an early 20th century former creamery. On the White River, in the East Valley, it is an inspired Vermont hide-away; It's a cozy space for two, yet large enough for your entire family or ski group.

Top guest favourite
A covered patio area captures the soothing essence of nature, featuring a Nordic cedar barrel sauna nestled among trees. Comfortable seating and a small table complement the space, while colorful flowers bloom in the foreground, adding a touch of vibrancy to the serene setting.
Guest house in Williamstown
4.98 out of 5 average rating, 254 reviews

The Tiny Home with Barrel Sauna

Charming + cozy tiny house, centrally located in the hills of middle Vermont. Rain or shine, enjoy the beautiful covered patio, relax in the cedar barrel sauna, roast marshmallows over a wood burning fire, explore all that Vermont has to offer or rest easy with our various spa amenities.

Popular amenities for Chelsea holiday rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Orange County
  5. Chelsea