Cottage vacation rentals in Windsor County

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Top-rated cottage rentals in Windsor County

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Guest favorite

Cottage in Woodstock

4.9 out of 5 average rating, 62 reviews

Globetrotter Retreat - Countryside Carriage House

Newly renovated, fully furnished house in the heart of Vermont countryside, minutes to GMHA, Woodstock village, Okemo Mountain, Killington Mountain, Saskadena Six, Green Mountains, hikes & lakes. Year round outdoor activities. Stand alone private carriage house sleeps 6 people in comfort. Private outdoor dining, propane grill and wood burning firepit. Amazing view of pastures and woods with a rolling brook. Parking for 2 vehicles and space for horse and snowmobile trailers (no animals allowed ).

Top guest favorite

The living area features a cozy sofa adorned with decorative pillows, positioned around a central coffee table. Natural light enters through a large window beside the door, illuminating the wood-paneled walls and rustic floor. A simple area rug adds texture to the space.

Cottage in Hartland

4.94 out of 5 average rating, 132 reviews

Adorable Dog Friendly Cottage w/FIOS

Bright and clean 2-story cottage on a 20-acre oasis. 10% off for guests using only one bedroom (cannot be combined with other discounts). Details in property description. 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. For groups or more space, view my other listing located on the same acreage: airbnb.com/h/hartlandvacationhome

Top guest favorite

A wooden deck features a pair of patio chairs and a small table, overlooking expansive rolling hills and greenery. A distant barn is visible beyond the lush fields under a bright blue sky dotted with fluffy clouds.

Cottage in Rochester

4.99 out of 5 average rating, 95 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.

Top guest favorite

A charming red cottage is set amidst vibrant autumn foliage, with trees in shades of orange and yellow surrounding it. A pathway covered in fallen leaves leads up to the cottage, which features a welcoming front porch and a sloped roof.

Cottage in Woodstock

5 out of 5 average rating, 35 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.

Top guest favorite

A spacious lawn is shown, featuring two buildings. One is a charming cottage with large glass doors, while the other is a main house with a traditional exterior. The ground is covered with fallen leaves, and trees line the background.

Cottage in Weston

4.97 out of 5 average rating, 102 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!!

Guest favorite

The cottage features a rustic log exterior, complemented by a sloped green roof. A welcoming porch area is adorned with flowers and greenery, creating a vibrant entrance. Nearby, a gravel path leads to the main entrance, surrounded by the natural beauty of the wooded landscape.

Cottage in Barnard

4.96 out of 5 average rating, 47 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.

Guest favorite

The exterior of a modern blue house is illuminated by warm lights, set against a twilight sky with a visible moon. Large windows reflect the serene surroundings, and the house is surrounded by tall grass and trees, suggesting a peaceful, rural ambiance.

Cottage in Vershire

4.93 out of 5 average rating, 96 reviews

The Vershire Fortress

Breathtaking views, mountain fresh air, and tranquility in the hill town of Vershire, VT; the Fortress looks out over the White Mountains to the East during the day and the Milky Way above at night. The property spans 6 acres that are available to all guests looking for a bit of snow-shoeing or a walk in the woods. Plus recent renovations! Designed and built by architect, Nick Fabrikant, it offers splendid open floor plans and incredible natural lighting through the many South-facing windows.

Top guest favorite

A spacious living area features a corner sectional sofa adorned with a cozy blanket and accented by a wooden wall with decorative planters. A rustic coffee table sits in front of the sofa, while a gas fireplace stove provides warmth and ambiance.

Cottage in Bridgewater

4.97 out of 5 average rating, 234 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 red cottage is nestled among lush trees, with string lights creating a warm ambiance. Four red Adirondack chairs sit around a small fire area, overlooking the peaceful stream that flows nearby.

Cottage in Bridgewater

4.98 out of 5 average rating, 57 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

The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.

Cottage in Windsor

4.97 out of 5 average rating, 403 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 a two-story house is depicted, featuring dark green siding and a welcoming entryway under a wooden porch. A manicured lawn surrounds the property, with a gravel path leading to the entrance. Trees and distant vehicles are visible in the background.

Cottage in Barnard

4.98 out of 5 average rating, 62 reviews

31 Lili West - across from Silver Lake on 5 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!

Guest favorite

A quaint cottage exterior is shown, featuring a deep blue façade with white trim and multiple windows. Snow falls gently around the structure, creating a serene winter scene. A light blue door opens to the right, while a small porch is visible in the center.

Cottage in Ludlow

4.91 out of 5 average rating, 134 reviews

Ludlow Village Guest Cottage with Prime Location

Renovated one bedroom, one bath guest cottage in Ludlow, Vermont. Prime ski location, 12 houses down from the Mountain Road entrance to Okemo Base Lodge. Anything you need can be found a short walk from the front door including a wide variety of restaurants, shops and bars for Après Ski. Sitting on the weekend and holiday shuttle route to Okemo, its the perfect spot to be! Cottage has a fully equipped kitchen and wifi for your technology needs.