Beachfront vacation rentals in Windsor County

Four Season River Retreat: Private beaches & more!

A river paradise! Situated on the iconic Black River, on 4 acres of woods and trails, our newly renovated farmhouse and barn has four bedrooms, two baths, a rec space, three beaches, and can easily host 8 guests. Brewery & hiking just minutes away. Perfect for summer & winter as it is located 12 minutes from Okemo and 40 minutes to Killington. Whether you are looking for a family vacation or a remote workspace, this all-season house is a perfect get-away to enjoy VT any time of the year.

Cheerful 4-br lakeside cottage- minutes to Okemo!

Relax year-round with the whole family at this peaceful waterfront home! Watch bald eagles swoop over the lake and enjoy fantastic boating and swimming in summer. Winter is a blast with outstanding downhill skiing at Okemo Mtn (10 min away), cross country skiing and sledding! Come to southern Vermont to sample craft beer, farm to table restaurants, farmer’s markets, antiquing and more! Guests have use of our canoe, kayaks, and paddle board. This is the perfect home for a relaxing getaway!

Lake House near Ludlow/Okemo and Killington

A Vermont lake house in the heart of spectacular Okemo Mountain Valley (6Miles to Jackson Gore Resort). Located high in the Green Mountains of Central Vermont, "Hearthside" rests peacefully on the waters edge of one of the most beautiful lakes in the world, Lake Ninevah, which hides nearly 1 mile above sea level. “Hearthside” has a long history of providing peace and tranquility, incredibly breathtaking landscapes, beautiful wildlife and exciting adventures no matter what season it is.

Riverfront Retreat in Stockbridge

3-bed hideaway nestled between Little Stony Brook and the White River, just off Rt 107 in scenic Stockbridge, VT. Watch bald eagles soar down the valley and fall asleep to the sound of the river. Year-round fun: tube the White River from your backyard, toast s’mores, nap in the shaded hammock, or stargaze from cushioned loungers. Ski Killington, Pico, or Sugarbush (20–40 min). Hike Green Mountain trails (15 min). Peace, comfort, and adventure—your perfect riverside retreat.

Renovated Family Lake~Ski House w/ gas fireplace

Our renovated home with new gas fireplace faces Echo Lake and backs onto an acre of woods. 4 bedrooms, 3.5 baths & can house up to 8 guests. Family friendly with a private dock for summer fun. Located 10 minutes from Okemo and 15 minutes from Killington ski areas. Mesh wifi routers to boost your internet connection. Whether you are looking for a family vacation or a remote workspace, this all season house is a perfect get away to enjoy Vermont anytime of the year.

Tranquil Ludlow Waterfront Retreat

Fully renovated in 2019, our four bedroom Ludlow, VT home has over 300' of river frontage on the west side of the Black River. Walk out to amazing fishing in one of Vermont's crystal clear rivers. Enjoy nature while your stress melts away or have some fun at the Okemo Resort boasting mountain biking, zip lining, and two 18-hole championship golf courses. Easy river access by kayak to Lake Rescue and a 2 min drive to the family-friendly beaches of Echo Lake.

3BR lakefront with dock, swim platform, & firepit