Vacation rentals with beach access in Windsor County

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Top-rated beach access rentals in Windsor County

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Guest favorite

Home in Fairlee

4.95 out of 5 average rating, 230 reviews

The Upper Valley Retreat

“Pictures Don’t Do It Justice!” A Massive 20 Acre Estate & Apple Orchard that sleeps 36+! Only 25min from Dartmouth! Majestic rolling lawns nestled along Brushwood Forest. Private outdoor space that will allow you to enjoy breathtaking sunsets or latenight stargazing. Everything you will need for an unforgettable retreat provided, including a pooltable, pingpong table, grill, firepit, & a fully stocked kitchen. On Baldtop’s Mountainside & only steps from access to trails & Minutes from the Lakes

Guest favorite

Tiny home in Fairlee

5 out of 5 average rating, 115 reviews

Private, 1 bedroom boutique tiny home

This boutique tiny home is situated in the picturesque Upper Valley of Vermont. The nearly 50 acres of private land is equal parts woods and water. You will wake to the mooing of dairy cows. Have your coffee on the porch while watching birds dive for their breakfast on the pond. Inside you will find every modern amenity. A fully appointed chef's kitchen. A living area filled with comfy furnishings and a cozy fireplace. Upstairs is a queen bedroom with an ensuite double showered bathroom. Heaven!

Guest favorite

Rental unit in Hartland

4.82 out of 5 average rating, 68 reviews

Private Riverside Studio* Upper Valley*Vermont

This unique place has a style all its own. Perfect for a traveling nurse or anyone who needs a relaxing getaway or a remote place to work. This studio apartment has river and garden views and is conveniently located in the New England Village of North Hartland. A 15-20 minute drive to Dartmouth College or DHMC. Take country walks across the twin covered bridges right from your doorstep. Relax on the front porch and watch the bald eagles and peregrine falcons search for prey along the river.

Guest favorite

Home in Hartford

4.85 out of 5 average rating, 53 reviews

Quechee Vermont Home

Forget your worries in this spacious and serene space. Nestled in the woods, listen to the sounds of nature from the deck, or take advantage of all that the area has to offer for outdoor recreation. Enjoy the outdoor fire pit and spacious deck for entertaining your guests. Each guest rooms has its own private bath, and the primary bedroom features a private outdoor deck. Enjoy the Air Fryer oven, 5-chamber pure drinking water system, soaking tubs at all bathrooms, top-quality cotton linens.

Guest favorite

Home in Lempster

4.96 out of 5 average rating, 28 reviews

Cozy Crescent Cottage

Peaceful cottage loaded w/4 season outdoor activities, 15 mi from Mt Sunapee, steps from ohrv/nature trail system, 160 feet of clean, private waterfront w/walk in water access, fire pit, & private boat dock. Swim, boat, hike, fish, bike, relax in the hammock & watch the sun set. Games & books, wood stove, fully stocked kitchen w/micro & gas range, fast wifi, 2 smart TVs, 5 beds. Towels, linens, toiletries, pantry basics and more incl to keep packing light....just bring clothes & groceries!

Superhost

Chalet in Stockbridge

4.85 out of 5 average rating, 137 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

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 Wallingford

4.99 out of 5 average rating, 105 reviews

Luxury Mountain Retreat- Pond Hill Place

Feel like you are a world away while only 10 min to Okemo and 35 min to Killington. Exquisite home set on 35 acres with modern decor throughout. Swim and fish in the two ponds in the summer; snowshoe and sled in the winter. Hot tub, wood burning fireplace, gas fireplace, pool table, Roku, Sonos speakers, and large deck with gas grill are just a few of the amenities in this oasis in the Green Mountains. Located minutes from Rutland Southern Vermont Regional Airport and the Appalachian Trail.

Superhost

Home in South Londonderry

4.85 out of 5 average rating, 133 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

This VERY NEW and VERY romantic treehouse is finished!!! The Honey Pond Treehouse is made especially for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…You will enjoy private hot tubbing, sauna time, relaxing, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes…biking & disc golf at Magic Mnt!

Guest favorite

Home in Ludlow

5 out of 5 average rating, 89 reviews

Stunning Views of Okemo - 3 Bedrooms, 3 Bath Home

Recently constructed on ten private acres with captivating views of Okemo resort. Three bedroom, three full bath modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or a glass of wine on the deck. Finished lower level with expansive views of the ski trails has 60" TV, games and comfy seating.

Guest favorite

Home in Plymouth

4.95 out of 5 average rating, 237 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Welcome to one of the most unique "retreats" in Vermont! Located on top of a private mountain, beautiful 100 mile views of the White Mountains. Ideally located between Killington (7 miles) and Okemo resorts, near Woodstock and Long Trail Brewery. Relax in the Jacuzzi hot tub while enjoying the views and stars. Private hiking trails, waterfalls, with trail maps! 7 miles to the beach at Camp Plymouth State Park. Secluded yet close to everything. New ventilation system.

Guest favorite

Cabin in Chittenden

4.96 out of 5 average rating, 110 reviews

Cabin on The Hill

Relax with the whole family at this peaceful place. Private, cozy, clean, comfortable getaway in Chittenden Vermont. This beautiful cabin is off the grid with solar power and push button generator. Chittenden is a small drive to endless recreational activities for every season. It is the perfect rustic space for a couple or a small family. It is centrally located between Killington and Rutland. Everything you need is within a 20 to 30 minute drive.