Vacation rentals with beach access in Windsor County

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Top-rated beach access rentals in Windsor County

Guests agree: these beach access rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Fairlee

4.95 out of 5 average rating, 229 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, 111 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, 66 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

4.87 out of 5 average rating, 52 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.

Superhost

Chalet in Stockbridge

4.86 out of 5 average rating, 134 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, 462 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

4.84 out of 5 average rating, 128 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 Plymouth

4.95 out of 5 average rating, 236 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, 109 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.

Guest favorite

Cabin in Stockbridge

4.91 out of 5 average rating, 35 reviews

Stunning Artist Retreat Cabin

About cabin: unique and tranquil located at #campwizbyvt, on an authentic old camp ground with a touch of modern and glamp thrown in. Located on the site of a former childrens camp on 250 acres with hiking and swimming (or cross country skiing) right out your door. At night you can relax around a beautiful stone fire pit under the stars. Check out our website for more info and info on our retreats: www/campwizbyvt/com

Guest favorite

Cabin in South Royalton

4.95 out of 5 average rating, 156 reviews

Cozy 4-season Cabin on Pond - "East Cabin"

Take refuge in a cozy log cabin with abundant access to Vermont's Green Mountains and rolling foothills. A quick drive to Woodstock and Quechee, the cabin is located on quiet dirt road with beautiful south-facing views overlooking the town of South Royalton, just a mile away. Spring-fed pond is steps from the cabin, take a dip! Follow the trails through the woods and fields and enjoy this pristine piece of Vermont.