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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Superhost

Yurt in S. Strafford

4.67 out of 5 average rating, 27 reviews

20' yurt at creek

This yurt is rustic, with double bed, futon and woodstove, kitchen area and table/chairs. It is down a hill (gravel wide steps and across the wetland on a 4’ wide bridge, then a rooted trail towards the creek), about 250’ from driveway Directions: Download before you leave the highway. From Rte 132 in S Strafford, go up Miller pond rd just 1.9 miles. Mailbox # 107 ( aka#1885) on right. Driveway on left. Park in pullout spot on right, across from generator shed. Trail is past kayak rack.

Cabin in Mount Holly

4.98 out of 5 average rating, 41 reviews

Lake House near Ludlow/Okemo and Killington

A Vermont vacation rental home 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

Private room in Hanover

4.93 out of 5 average rating, 30 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

Cottage in Acworth

5 out of 5 average rating, 17 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 favorite

Castle in Clarendon

4.98 out of 5 average rating, 464 reviews

Kingsley Grist Mill, Covered Bridge and Waterfall.

America's only original Grist Mill & Covered Bridge residence, as seen on HGTV's "You Live in What?", (Se.2. ep.1) & worldwide on the Netflix travel series "World's Most Amazing Vacation Rentals" (Se. 2, ep 7). Join us for our 10th season as central Vermont's iconic adult getaway featuring private beach on Vermont's warmest river with tethered, relaxing, float tubes & two private decks overlooking Mill River's secluded waterfall. Come make history with us ! Near Killington & Okemo Mtns.

Guest favorite

Home in Cavendish

4.93 out of 5 average rating, 42 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 get-away to enjoy VT any time of the year.

Cottage in Ludlow

5 out of 5 average rating, 10 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!

Home in Strafford

New place to stay

Charming Vermont Farmhouse

A wonderful place to gather with family and friends at the Churchill Tree Farm. Nestled on a dirt road up in the Vermont Hills, enjoy beautiful stars, hike trails, bike, and walk and take in spectacular views on this amazing property. Relax around a campfire, roast marshmallows or cozy up with a good book by the gas fireplace. A tranquil and peaceful place to enjoy family, friends, wildlife and fun. House is equipped with high-speed fiber internet. Swimming pond available 2025.

Superhost

Cabin in Ludlow

4.74 out of 5 average rating, 220 reviews

Beautiful winter cabin near Jackson Gore

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, and Granite countertops in kitchen. This is an amazing value!

Home in Plymouth

4.96 out of 5 average rating, 52 reviews

Renovated Family Lake~Ski House w/ new 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

Home in Ludlow

4.89 out of 5 average rating, 83 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.

Condo in Killington

4.5 out of 5 average rating, 10 reviews

Woods Resort Village 43 walk to all the amenities

Located within the Woods Resort and Spa, this cozy and comfortable 2-bedroom plus loft, 2-full bath townhome has all you need for the ideal trip to Killington. Besides being minutes away from the action of the bars and restaurants in town, this condo rental in Killington also has a centralized location that will get you to some of the best spots for outdoor recreation with no hassle at all! With the rare second-bedroom-plus-loft floor plan,