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 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, 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 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, 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 grassy area is framed by a sturdy stone wall and a large tree, providing shade. Beyond the wall, rolling hills and trees create a natural backdrop, enhancing the serene outdoor setting.

Cottage in Reading

4.89 out of 5 average rating, 75 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 cozy living area is complemented by a rustic brick wall and warm wood accents. A light-colored chair with a cushion faces a simple wooden coffee table. To the rear, the full kitchen is visible, featuring white cabinets and modern appliances.

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!!

Superhost

A serene outdoor space features two Adirondack chairs positioned around a fire pit, surrounded by lush green grass and a backdrop of dense trees. The calming natural setting invites relaxation and outdoor gatherings.

Cottage in Mendon

5 out of 5 average rating, 5 reviews

The Mendon Cottage: Cozy Home. Killington / Pico

Recently renovated 2BR/2BA cottage in Mendon, VT, near Pico & Killington Ski Resorts, & Rutland. Sleeps 6: 1BR w/ queen & ensuite, 2nd BR w/ 2 double beds. Additional BA, laundry room, living room w/ smart TV, fully equipped kitchen & dining area. High-speed WiFi, mini splits for heat/AC, front & back decks, BBQ grill. All new furnishings offer modern comfort & rustic charm. Ideal for skiing, exploring, or relaxing in the mountains. Perfect base for your VT adventure! Discounted ski rentals.

Guest favorite

A quaint cottage is set against a backdrop of rolling hills, featuring a blue exterior and a red door. A wooden table and chairs are positioned on a grassy area, surrounded by landscaped gardens with colorful flowers. Nearby trees and plants add to the serene environment.

Cottage in Hartland

4.93 out of 5 average rating, 116 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

The exterior of a country cottage is shown, featuring a wooden porch with stacked logs and a white picket fence. Lush green trees surround the property, and a rustic barn structure is visible in the background, set against a cloudy sky.

Cottage in Londonderry

4.88 out of 5 average rating, 67 reviews

Vermont Country Cottage(Near Village w/Magic View)

This cute, country cottage offers 2 bedrooms, 1 bath with a treehouse loft in the bunk room. The floors are wood, kitchen is custom built with stainless steel appliances, bathroom vanity is custom built using the original kitchen sink from the home, and the twin size bunks are built in as well. There is a very large yard. There are 4 ski resorts within 20 minutes, the Weston Country Store and play house are 5 minutes up the road, and you can walk to the local farmers market every Saturday.

Guest favorite

A covered exterior deck is featured, showcasing a wooden dining table surrounded by six woven chairs. The area is illuminated by hanging lights and overlooks a setting with lush greenery and autumn-colored trees, providing a serene outdoor dining experience.

Cottage in Bridgewater

4.97 out of 5 average rating, 215 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 serene pond is framed by lush greenery and wildflowers, with a wooden dock extending into the water. Two simple wooden chairs are positioned at the edge of the dock, inviting relaxation and enjoyment of the peaceful natural surroundings.

Cottage in Windsor

4.97 out of 5 average rating, 383 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

An outdoor area is softly illuminated at night, showcasing a selection of red lounge chairs arranged around a fire pit. The screened-in porch is visible to the right, offering a glimpse of the tranquil lake and lush surroundings, creating a serene evening atmosphere.

Cottage in Plymouth

4.96 out of 5 average rating, 24 reviews

Cute Cool Cabin! Plymouth, Vermont.

3BR & 3BA~Fireplace~Fire Pit~Hot Tub~Dog-Friendly~Screened-In Porch~Outside Shower~Private Beach & docks~Canoe~beautiful lake view~waterfowl. We provide generous premium amenities of fine linens~plush towels~toiletries~high-end cookware~grills~spice cabinet~clean~well-stocked & organized. We provide better & more!! Rates include cleaning. Plus Vt. tax. Airbnb's booking fees added by Airbnb. Rustic charm. Modern amenities. Between Killington & Okemo 15 minutes.

Top guest favorite

A spacious deck is featured, furnished with a dining table and chairs beneath an umbrella. Large windows provide views of the surrounding trees, while the wooden surface adds a natural touch. The path leading away from the deck is visible, surrounded by greenery.

Cottage in Reading

4.95 out of 5 average rating, 156 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

The exterior of the Guest Cottage features a modern design with a white facade and dark accents. A spacious porch with two rocking chairs overlooks a lush green lawn, surrounded by trees. The structure benefits from ample natural light, highlighting its inviting atmosphere.

Cottage in Ludlow

5 out of 5 average rating, 7 reviews

NEW Guest Cottage on 23 Acres

Guest Cottage is situated on 23 acres with a hot tub. This separate living space is 50 feet away from the main house at Revival that is also for rent airbnb.com/h/revivalresort. The Guest Cottage at Revival sleeps 4 comfortably. Bedroom has a Queen bed and pullout sofa in the living room. Heat & Air conditioning, full kitchen, full bathroom including a washer & dryer. 2 Smart TV's and breathtaking views of Okemo!