Cottage vacation rentals in Windsor County

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Top-rated cottage rentals in Windsor County

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Guest favorite

A stone pathway is lined with soft glow from solar lights, guiding the way through a lush green yard. Flower pots with vibrant yellow and pink blooms add color to the scene, creating an inviting atmosphere for outdoor enjoyment.

Cottage in Weston

5 out of 5 average rating, 39 reviews

Ski cottage near Okemo, Bromley, Stratton

Peaceful centrally located 4 bedroom 3 bath cottage to enjoy any season. Ski-15 min drive (Okemo, Bromley, Magic, and Stratton)15-20 minutes to nearby lakes, hiking, golf,fishing, ATV’s/snowmobiles, visit wineries and breweries. Adventure out go shopping or just have a relaxing time in picturesque Weston. Kick back by the fireplace, take in the beautiful scenery from the covered porch, play on the arcade, make s’mores by the fire pit and enjoy! Make memories with your family and friends today

Guest favorite

An aerial view captures the surrounding lush green landscape of the sanctuary, with rolling hills and dense woods. The cottage is seen nestled within the trees, illustrating a blend of nature and tranquility in this expansive 20-acre environment.

Cottage in Hartland

4.93 out of 5 average rating, 120 reviews

Adorable Dog Friendly Cottage w/FIOS

Bright and clean 2-story cottage on a 20-acre oasis. With a view of the hills, flanked by woods and open pastures, the cottage includes 2 bedrooms (1 up w/Queen, 1 down w/full bed, 1 bath (2nd floor - shower only), kitchen/living/dining area (2nd floor), and laundry. 10% off for guests using only one bedroom (cannot be combined with other discounts). Details in property description. For groups or more space, view my other listing located on the same acreage: airbnb.com/h/hartlandvacationhome

Top guest favorite

A living area offers a spacious feel with light wood flooring and a dining table adjacent to a large sliding glass door. Outside, two wicker chairs are positioned on a private deck, overlooking expansive views of rolling hills and greenery under a partly cloudy sky.

Cottage in Rochester

4.99 out of 5 average rating, 91 reviews

Cozy cottage near Killington & Sugarbush

Escape the real world at this charming and cozy cottage tucked away in a corner of 17 acres of rolling grassy hills. Take in the unmatched views of the hollow from the living room or wrap-around porch. Endless nearby trails for hiking/biking/xc skiing, and Rochester's stores, cafes, and restaurants are less than 10 minutes away. Grocery store, berry picking, lakes, swimming holes, golfing, restaurants, breweries, and wineries all within an easy drive. Killington/Sugarbush both ~35 minutes away.

Guest favorite

A modern dining area features a large wooden table surrounded by four leather chairs and two woven side chairs. Large windows with black curtains provide natural light, while French doors lead to the outdoor area. Minimalist decor includes framed artwork and a potted plant.

Cottage in Woodstock

5 out of 5 average rating, 33 reviews

Modern Cottage Near Skiing, Trails & Fine Dining

Enjoy 360-degree mountain views in this peaceful cottage on 5 acres in rural Woodstock. Less than 15 minutes to charming Woodstock Village with shops & fine dining & 20 minutes to world-class Killington skiing. Walk around on cozy heated floors, enjoy brand new mattresses, and a fully equipped modern kitchen with granite countertops. Nearby walking, biking, and snow mobile trails abound. Small sledding hill on-site for the littles. Plenty of space on 3 levels for privacy for groups or families.

Guest favorite

A flowing stream meanders over smooth stones, surrounded by bare trees and patches of snow. The sound of water over rocks creates a soothing atmosphere in the natural landscape, which showcases a blend of winter and early spring elements.

Cottage in Reading

4.9 out of 5 average rating, 77 reviews

Stone Wall Cottage, Stonewall : GMHA, Okemo

Extended Stay Discounts. Enjoy the beauty of old Vermont in our bright and airy cottage. The romantic upstairs bedroom holds a new queen bed. Use the adjacent upper deck for al fresco dining as you view open fields and mountains, or pleasure in the stunning night sky. Cooking is easy with a full fridge, new gas range, & generous counter space.The spacious bathroom offers a shower big enough for two. Great WiFi, separate work areas, plus a comfortable queen sofa-bed. Rainbow /Safe Space.

Top guest favorite

A compact bathroom space is displayed, featuring a white toilet next to a small sink with a faucet. Natural light filters in through a window, illuminating the tiled floor and pale wall paneling. A mirror is mounted above the sink, adding functionality.

Cottage in Weston

4.97 out of 5 average rating, 100 reviews

Charming Mountain Cottage **NO CLEANING FEE**

Enjoy a charming cottage on the side of a hill in beautiful Weston, Vermont. You'll have the entire building to yourself (it's a stand-alone structure) to come and go as you please. My goal is to provide a five-star experience for five-star guests. I think little details like Ralph Lauren bath sheets, freshly-pressed bed linens, and duvet covers that are laundered between each guest make a difference. If you agree, you're probably the type of guest I'd enjoy hosting! Motorcycle friendly!!

Top guest favorite

An outdoor patio space is illuminated by warm string lights, showcasing a stone floor and various seating options. A fire pit is surrounded by modern seating, and soft foliage adds to the natural ambiance. The cozy cabin structure is visible, enhancing the inviting setting.

Cottage in Barnard

4.95 out of 5 average rating, 39 reviews

Andas Hus: Little Luxury

Andas Hus [Breathe House] : A tiny cottage set in an expansive space. This designer cottage, with its chef’s kitchen and modern bath, manages to take up a much larger space than its 800 sq feet would suggest. Set on 52 acres of forested Vermont hillside, with maple, apple, pine and birch groves spread throughout, Andas Hus is the perfect place to just…breathe. The generous outdoor space makes for three season enjoyment of all that VT has to offer, while winters by the fire are equally magical.

Top guest favorite

A rustic kitchen features wooden cabinetry and a contrasting dark countertop. Natural light streams in through multiple windows, illuminating the workspace. A rug lies on the floor, and kitchen essentials are neatly organized on shelves and countertops.

Cottage in Hartland

4.99 out of 5 average rating, 84 reviews

Private cottage perched on Lull's Brook

A nature lovers retreat. Located in the heart of the village, this 672 sq foot space feels private and removed. It sits perched, a stone's throw above the brook. Watch a Kingfisher dive for a brook trout, or a Mallard or Merganser swim upstream with ducklings. Peach, apple and pear trees surround the house. In the evening, the Skunk Hollow Tavern is available for a delicious meal, almost directly down the driveway and across the street or venture to the village of Woodstock just 8 miles away.

Guest favorite

Cottage in Bridgewater

4.97 out of 5 average rating, 225 reviews

Newly Renovated, Hot tub, 2min to Killington lift

Stone’s Throw Vermont is a 3 bed/1.5 bath cottage with hot tub, fireplace, and space for 6 guests conveniently located in central Vermont. Placed right on the US-4 corridor; you’re 2 minutes from the Killington Ski Resort’s Skyship Ski Gondola escorting you to the world class amenities of Killington Resort, 5 min from the best craft beer in the region at Long Trail Brewery, 10 min to Echo Lake, and 20 min from the shops and cafes of Woodstock, VT. Truly everything is a Stone’s Throw away.

Top guest favorite

A black dog stands in shallow water, partially submerged, with droplets clinging to its wet fur. A red ball, resting in the water nearby, creates ripples as the dog gazes curiously at it. Lush greenery surrounds the scene, softly diffusing the sunlight.

Cottage in Bridgewater

4.98 out of 5 average rating, 52 reviews

Riverside Cottage - Bridgewater Vermont

Welcome to our cozy riverside cottage along the Ottauquechee River. Note: we're on Rt. 4 which is great for access but there is some road noise. Block that out as you sit by the river & watch the ducks go by, or cozied up on the couch next to the woodstove A perfect spot for your Vermont adventures! You'll be 5 miles away from Killington's Skyeship, 10 Miles away from Woodstock, & nearby to many local attractions & restaurants Enjoy the game room & extra space in the converted garage!

Top guest favorite

A stone fireplace is seen with warm flames flickering from burning logs. The fire creates a cozy ambiance against the rustic stone backdrop, while the wooden floor reflects the light from the fire, enhancing the inviting atmosphere of the space.

Cottage in Windsor

4.97 out of 5 average rating, 395 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Guest favorite

The exterior of the cottage features dark blue siding with white window frames. Two windows are adorned with flower boxes, while two green chairs are positioned on the patio. A small deck is visible to the left, surrounded by lush greenery.

Cottage in Reading

4.93 out of 5 average rating, 162 reviews

Shattuck Hill Cottage

Cozy two bedroon one bath cottage on 12 acres perfect for a visit to the Woodstock area. The cottage is 6 miles from the Green Mountain Horse Association. Our property connects to miles of riding and hiking trails. We have fenced pasture for your horse, a run in shed and are directly on the dirt roads and trails. You can ride, ski, snowshow, bike, hike or antique from our cottage. Come enjoy all Vermont has to offer. This is a non smoking property.