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 Ludlow

5.0 out of 5 average rating, 13 reviews

The Little House

Eight minutes to Okemo and set back on the top of a hill, our ski cottage has all the charm of Vermont living, updated with everything you need. Our home is clean and private. With an open kitchen, living and dining space, there's plenty of room to enjoy after a long day hiking, skiing, or enjoying the outdoors in Vermont. Cuddle up and enjoy your morning coffee in front of the gas stove, or open up the slider and step out into the private backyard to see the wildlife that often passes through.

Jul 30 – Aug 6

G$25,822 GYD per night

Guest favorite

Cottage in Woodstock

4.94 out of 5 average rating, 33 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 ).

Dec 19 – 26

G$61,273 GYD per night

Guest favorite

Cottage in Woodstock

5.0 out of 5 average rating, 17 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.

Aug 4 – 11

G$74,823 GYD per night

Guest favorite

Cottage in Hartland

4.97 out of 5 average rating, 420 reviews

Breeze Hill Cottage

This cozy two bedroom home sits on a rural dirt road overlooking fields, woods, and the NH mountains. Watch birds from the window, relax on the patio, and enjoy the flower gardens. The cottage boasts modern amenities mixed with antiques. Please note: if we don’t respond to an Airbnb message and you need to speak with us, call us on our phones day or night!!! We have had people message us when we were asleep and so we have not been aware and have not responded. Call us! We will hear the phone!

Nov 17 – 24

G$25,668 GYD per night

Guest favorite

Cottage in Weston

4.97 out of 5 average rating, 91 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!!

Jan 9 – 16

G$40,586 GYD per night

Guest favorite

Cottage in Hartland

4.98 out of 5 average rating, 65 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.

Oct 9 – 16

G$66,109 GYD per night

Guest favorite

Cottage in Bridgewater

4.96 out of 5 average rating, 142 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.

Jul 29 – Aug 5

G$52,176 GYD per night

Guest favorite

Cottage in Bridgewater

5.0 out of 5 average rating, 9 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!

Sep 13 – 20

G$52,589 GYD per night

Guest favorite

Cottage in Barnard

5.0 out of 5 average rating, 48 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!

Dec 19 – 26

G$40,774 GYD per night

Guest favorite

Cottage in Ludlow

4.92 out of 5 average rating, 120 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.

Jul 21 – 28

G$27,021 GYD per night

Guest favorite

Cottage in Windsor

4.97 out of 5 average rating, 319 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.

Nov 18 – 25

G$28,211 GYD per night

Guest favorite

Cottage in Woodstock

5.0 out of 5 average rating, 26 reviews

"The Barn Cottage" at Kedron Valley Farm

Welcome to the “Barn Cottage" at the iconic Kedron Valley Farm. This tranquil, historic cottage is conveniently located directly across from Green Mountain Horse Association, and just a short stroll to the charming South Woodstock Village and 6 miles to the Woodstock Green. Acres of spectacular hiking and biking trails just outside your back door. Nearby cross-country & downhill skiing. Comfortable, well-appointed, and tidy.

Jul 21 – 26

G$84,100 GYD per night