Beachfront vacation rentals in Windsor County

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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 favorite

A cozy seating area is present, featuring a floral-patterned chair with a comfortable cushion. Nearby, a wooden chest serves as a storage solution. Natural light filters through a window, illuminating the space and highlighting potted greenery on the floor.

Private room in Hanover

4.94 out of 5 average rating, 34 reviews

Single Room at Dartmouth College; The East Room

A place to call home for 1 night or 1 month at this unique and tranquil getaway. Rustic, clean cottage within easy walk to Dartmouth College in the heart of the Upper Valley Region of NH...Walk to Main Street with outdoor cafes and upscale boutiques. Hanover has small town charm teeming with the academic pulse of lifelong learning from around the world. If you are seeking a central location for your visit to both VT and NH this is an ideal starting point with appeal to just about everyone....

Guest favorite

A classic knotty pine cottage is reflected in the calm waters of the lake. The screened porch features a single chair, while a swim raft and dock are visible nearby. Lush green trees surround the property, enhancing the serene natural setting.

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.

A wooden dock extends into a calm lake, surrounded by lush, green trees and rolling hills. The water's surface is smooth, reflecting the clear blue sky. A swimming ladder is attached to the dock, inviting leisure and exploration.

Cottage in Ludlow

4.76 out of 5 average rating, 17 reviews

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!

Top guest favorite

The red farmhouse features a spacious wrap-around porch with white railings, surrounded by greenery. Large windows allow natural light to fill the interior. The roof slopes distinctly, providing character to the structure, while power lines run along the front, connecting it to the surroundings.

Home in Cavendish

4.94 out of 5 average rating, 52 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 favorite

A serene winter landscape features a frozen lake bordered by a tree line. Snow-covered ground reflects the soft sunlight, while distant hills rise under a partly cloudy sky. The scene conveys a tranquil, natural setting in a peaceful, secluded area.

Cabin in Mount Holly

4.98 out of 5 average rating, 52 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.

Guest favorite

An aerial view of a green lawn adjacent to Lake Pauline features a circular fire pit surrounded by red and blue chairs. Two wooden benches are positioned nearby under the shade of several trees, offering a peaceful outdoor retreat.

Cabin in Ludlow

4.74 out of 5 average rating, 270 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 favorite

A serene riverfront setting features a fire pit surrounded by four wooden adirondack chairs, positioned on a grassy area. The river is visible in the background, flanked by lush trees under a soft twilight sky.

Home in Stockbridge

5 out of 5 average rating, 12 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.

Guest favorite

An open living space features a comfortable sofa adorned with orange throw pillows. Large windows provide a view of the greenery outside, while natural light brightens the warm wooden floors. A dining table is visible in the background, creating an inviting atmosphere.

Home in Plymouth

4.97 out of 5 average rating, 61 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.

Superhost

A wooden deck is located alongside a lush, green riverbank, surrounded by tall trees. Two blue chairs are positioned on the deck, overlooking the tranquil stream, which is framed by vibrant foliage. A kayak is visible on the river, inviting exploration.

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 favorite

The Kingsley Grist Mill is positioned alongside a flowing river, surrounded by trees showcasing autumn colors. A historic covered bridge is visible in the distance, enhancing the landscape. The building features multiple stories with varying textures and roof styles, reflecting its rich history.

Castle in Clarendon

4.98 out of 5 average rating, 491 reviews

Kingsley Grist Mill, Fall & Winter Wunderland, OMG

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.