Waterfront vacation rentals in Windsor County

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Windsor County

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

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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

Cabin in Randolph

4.95 out of 5 average rating, 143 reviews

Remote, pond view log home, fully loaded, sleeps 6

Enjoy our remote, easily accessible, immaculate, pond-side cabin, set in nature on 109 acres: pond, woods, fields, and trails; with high-speed internet and smart TV! Sleeps 6, including a queen bed, 2 bunk beds, and a sleep sofa. Fully equipped kitchen, including a full-sized refrigerator, microwave, Keurig coffee maker, and many other amenities. Screened in porch. Views from every room! In the heart of the Vermont ski corridor. Explore the trails, and our meditation yurt when available!

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

Chalet in Woodstock

4.98 out of 5 average rating, 100 reviews

Falcon House: VT Chalet w/Sauna, Bike to Village

Welcome to Falcon House! A modern VT chalet w/sauna at the edge of a 60 acre forest ∙ Outdoor Finnish sauna, shower, yoga platform & hiking trails ∙ 5 min to Woodstock village, 20 min to ski Killington ∙ Spotlessly clean, tastefully furnished, well stocked with thoughtful amenities ∙2 bedrooms, 2 full baths. Lofted king master has ensuite +Lower level den w/double futon ∙ Chefs kitchen, fireplace, 2 TVs & WiFi ∙ Brookside deck w/BBQ & dining ∙Follow Falcon House on Social @falcon_house_vt

Guest favorite

Guesthouse in Springfield

4.86 out of 5 average rating, 349 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

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

Tiny home in Chester

4.99 out of 5 average rating, 109 reviews

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Tiny living at its best! Welcome to Bearfoot Cottage, a custom-designed Tiny House escape nestled on 15 acres in Southern Vermont. Enjoy the entire property to yourself with hot tub, Char-Griller BBQ, & Solostove firepit. Hike or snowshoe Ladybug Trail to our babbling brook. Then explore the best of Okemo Valley all at your fingertips! Ski/Snowboarding (+more Winter sports), biking, hiking, fishing, dining, breweries, and live music/nightlife. Your vacation is what you make it!

Guest favorite

Guest suite in Clarendon

4.95 out of 5 average rating, 128 reviews

River House Apartment - Dog friendly

Entire downstairs of a house with one double bed. There is nice bathroom with shower. There is a microwave, coffee, massage chair, outdoor grill and picnic table. Internet and cable provided with fire stick for the TV. Fire pit and hot tub are shared by other guests. Up to three and all size dogs or pets are allowed and welcome. The three acres has a lovely place for them to run and has been sprayed for ticks and mosquitos. Please note: key replacement $30 if lost or taken

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 Woodstock

4.98 out of 5 average rating, 185 reviews

Cozy Log Cabin, Peaceful Retreat

Cozy Cabin doesn’t charge an additional cleaning fee to our guests! We focus on a comfortable, relaxed, Vermont experience. If you’re looking for a peaceful, yet accessible location, we are situated on 15 acres located between Woodstock Village & Killington. There’s fiber WiFi, Hulu +Live TV w/local channels, ESPN+, Disney+. Also Amazon movies & music, Netflix, Paramount+, & Peacock. The Rec Room has a pool table, darts, lounge, gym and a desk for remote work.

Guest favorite

Home in Londonderry

4.98 out of 5 average rating, 112 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

Guest favorite

Yurt in Mount Holly

4.85 out of 5 average rating, 211 reviews

Love Shack Yurt on Star Lake (100% off grid)

Glamping at its finest. Bring everything but the bed. Enjoy sunsets and star gazing lakeside. No running water or electricity. Clean & custom built outhouse for a toilet. You will need to bring bedding, size king. Please note: self cleaning policy. Leave it in great condition for your fellow travelers. Woodstove for heat, provide your own wood. One King Bed, One Single Bed both with mattresses and top sheet ONLY. IG@YURTlilyPAD