Cottage holiday rentals in Windsor County

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.

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.

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!!

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.

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.

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.

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.

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.

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!