Cottage vacation rentals in Windsor County

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Top-rated cottage rentals in Windsor County

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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, 89 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 charming red cottage is surrounded by a thick blanket of snow, nestled among tall, bare trees. The snow-covered pathway leads to the front entrance, where a white awning provides shelter. The serene winter landscape is enhanced by the gentle fall of snowflakes.

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

A serene outdoor area is depicted by the brook, featuring a small wooden deck with a seating arrangement. Surrounding greenery includes lush grass and various trees, contributing to a natural environment. The gentle flow of the brook can be seen nearby.

Cottage in Hartland

4.99 out of 5 average rating, 83 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

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, 118 reviews

Adorable Dog Friendly Cottage w/FIOS

Bright and clean 2-story cottage on a shared 20-acre sanctuary. 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 bathroom (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). See details in property description. Dog sitting & walks sometimes available - please inquire for rates & info ahead of time.

Guest favorite

Cottage in Bridgewater

4.97 out of 5 average rating, 222 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, 47 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

Cottage in Windsor

4.97 out of 5 average rating, 389 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

A private three-season porch features large glass doors providing views of the surrounding greenery. Comfortable seating includes a cozy sofa, a low table, and two small armchairs. Natural light fills the space, which has a wooden ceiling and stone flooring.

Cottage in Barnard

4.98 out of 5 average rating, 60 reviews

31 Lili West - across from Silver Lake on 6 acres

Recently built 2 unit house (this is the west side) across from Silver Lake in Barnard, steps from the General Store. Gorgeous views and a huge stretch of property with a tennis court. Unit includes a 3 season private porch. Great local restaurants in Barnard, Woodstock and South Royalton, and easy access to highways and other routes to local ski mountains. Direct access to the VAST trail system, and trailer parking for snowmobile groups. Great for families and big groups!

Top 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

4.94 out of 5 average rating, 159 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.

Guest favorite

A comfortable outdoor seating area is featured on a wooden deck. Wicker furniture, including a sofa and chairs, is arranged around a coffee table. An umbrella provides shade, while lanterns are positioned on the ground. Lush greenery surrounds the space, contributing to a serene atmosphere.

Cottage in Chester

4.89 out of 5 average rating, 94 reviews

Quaint stone house!

⭐️ 2022 Rockingham Old House Award ⭐️ Take it easy at this unique and tranquil getaway. The Cairn of Vermont is an 1840s stone house located in the sleepy remnants of Bartonsville Village, now part of Chester, VT. 20 minutes to skiing and hiking, biking and the great outdoors are all around you! Less than 5 minutes to Vermont Country Store and make your way home through the Bartonsville Covered Bridge!