Beachfront vacation rentals in Windsor County

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Windsor County

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Guest favourite

Cottage in Acworth

5 out of 5 average rating, 19 reviews

Classic lakeside cottage with gorgeous sunset view

Live the lake lifestyle in a classic seasonal knotty pine cottage. Paddle, fish, swim, boat & stargaze by the fire pit. Huge screened in porch for meals overlooking the water. Good-sized kitchen with dishes, glasses, pots and pans. Enjoy your own dock and beach area. Bring up to 20’ boat. This is a classic 1936 cottage, there are narrow stairs going up to the 2nd floor that may not be suitable for everyone. 1 BR is on 1st fl. WiFi. Linens. TV. Firewood. Swing set. Swim raft. Kayak. Paddle boat.

Guest favourite

Home in Cavendish

4.94 out of 5 average rating, 49 reviews

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 getaway to enjoy VT any time of the year.

Guest favourite

Cabin in Mount Holly

4.98 out of 5 average rating, 49 reviews

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.

Cabin in Ludlow

4.74 out of 5 average rating, 258 reviews

Beautiful Lake Cabin - Okemo - Great for Famlies

The cottage (off Route 100) right on on Lake Pauline and is perfect for a family vacation or couple get away. Amazing backyard, Deck, Firepit and Grill for nice summer activities in beautiful Vermont. The cottage is about 1.5 miles from the Okemo or 1.0mi Jackson Gore with activities during the summer. The house has all that you need to make your stay cozy including Tv's in every room, recently updated tile bath, Granite countertops in kitchen & exterior paint. Amazing value!

Top guest favourite

Home in Stockbridge

5 out of 5 average rating, 5 reviews

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.

Superhost

Home in Plymouth

4.97 out of 5 average rating, 60 reviews

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.

Home in Ludlow

4.87 out of 5 average rating, 94 reviews

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.

Top guest favourite

Castle in Clarendon

4.98 out of 5 average rating, 479 reviews

Kingsley Grist Mill, w/ Private Beach & Waterfall

One of the "World's Most Amazing Vacation Rentals " as seen on the exciting NetFlix series, s.2, ep.7 and on HGTV's "You Live in What?, s.2, ep.1. Join us this season for the romance, the history, the breakfast, the natural mineral spring tap water, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. Come make history with us ! Near Killington & Okemo Mtns.