Waterfront holiday 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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Top guest favourite

A cozy room features a spacious bed with a plaid blanket, a woodstove positioned against a natural wood accent wall, and a rocking chair. Multiple windows allow natural light, highlighting the wooden ceiling and fir floor. A small dresser complements the room's rustic charm.

Cabin in Bethel

Firefly Cottage

Relax in this calm Nordic-style space. Rocking chairs on the porch overlook a pond, meadow, and spectacular seasonal fireflies. 140 woodland acres to explore with old (rough) logging trails with views, sheep and chickens you can feed. High ceilings, scenic window, woodstove, indoor waterless toilet, outdoor coldwater sink and outdoor private hot shower (when above freezing); available sauna at main house. 35-45 min to main ski areas. Most pets ok! Owner's home conveniently close but out of view.

4.97 out of 5 average rating, 112 reviews

Top guest favourite

A cozy living area showcases a comfortable sofa adorned with patterned cushions and a soft throw. A rustic coffee table sits in front, complemented by stylish armchairs. Natural light filters through large windows, illuminating the modern kitchen with dark cabinetry in the background.

Tiny home in Fairlee

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!

5.0 out of 5 average rating, 191 reviews

Guest favourite

Home in Bridgewater

Breathtaking Riverfront Retreat w/Mountain Views

Thoughtfully designed to elevate every moment of your Vermont getaway, our home offers a comfortable & uniquely historic experience, along with panoramic views of the beautiful Ottauquechee River. Perfectly nestled between the vibrant towns of Woodstock and Killington, guests have incredible hiking, skiing, golfing, shopping, leaf peeping, delicious dining, and so much more right at your finger tips. Wonderful for families, couples, or small groups looking to explore all that VT has to offer!

4.97 out of 5 average rating, 110 reviews

Top guest favourite

A modern chalet is situated among lush greenery, featuring a sloped roof and large windows. A cozy outdoor seating area surrounds a fire pit on a grassy lawn, inviting relaxation in a natural setting. A storage area for firewood is visible beside the structure.

Chalet in Woodstock

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

4.98 out of 5 average rating, 120 reviews

Superhost

An aerial view captures a cozy cottage situated along the Connecticut River. Lush greenery borders the water, and a small pathway leads to the cottage. A boat glides along the river, highlighting the serene setting surrounded by forests and rolling hills.

Guest house in Springfield

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.

4.84 out of 5 average rating, 413 reviews

Top guest favourite

A red cabin with a metal roof is framed by tall yellow wildflowers and lush greenery. The spacious porch features white railing and is decorated with several seating areas, offering a serene view of the surrounding landscape.

Cabin in Bridgewater

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

4.93 out of 5 average rating, 129 reviews

Guest favourite

A newly renovated lakefront home is showcased, featuring a spacious deck with comfortable seating and a covered lower level area. Soft lighting illuminates the exterior, highlighting the modern finishes and architectural details against a twilight sky.

Home in Ludlow

VT Lakefront House, Lake Fun, Fall Foliage and Ski

Newly renovated, air conditioned, lake front home with a hot tub, fire pits and modern finishes. Tons of space, super comfortable beds. Plus TWO LARGE bonus rooms. Year-round fun; swim, kayak, golf and fish in the summer; hike and fall foliage in the fall and ski in the winter. 7 minutes from Okemo and 22 minutes from Killington. Cook with a stunning view of the lake, watch a movie by the fire or hottub. Outdoor shower, game room, movie room, screened porch and much more!

4.88 out of 5 average rating, 104 reviews

Top guest favourite

A spacious living room features a comfortable sofa and armchair, enhancing relaxation. A large television is positioned in front, with decorative elements and artwork on the walls. Soft lighting from lamps and windows creates a welcoming ambiance in the well-designed space.

Guest suite in Clarendon

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

4.95 out of 5 average rating, 229 reviews

Top guest favourite

An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.

Home in Londonderry

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). STR License 26-23-185

4.99 out of 5 average rating, 155 reviews

Top guest favourite

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

Kingsley Grist Mill Waterfall & Private Beach 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. No cleaning fees added. Come make history with us ! Near Killington & Okemo Mtns.

4.98 out of 5 average rating, 520 reviews

Guest favourite

A charming riverside home is displayed surrounded by lush greenery. The structure features a light grey facade, bright red shutters, and a sloped metal roof. A spacious yard with hydrangeas in bloom is visible, providing a welcoming outdoor space.

Home in Woodstock

Riverfront Retreat Minutes from Woodstock Village

Relax with the whole family at this spacious & peaceful riverside home. Minutes from downtown Woodstock and Killington Mountain Resort, you can spend quality time with family and friends. Perfect for any season, you and your guests can enjoy a bluebird day on the slopes, a perfect summer morning on the golf course, or a crisp afternoon hike during foliage! We’d love to host your weekend getaway, week long vacation or longer!

4.96 out of 5 average rating, 101 reviews

Top guest favourite

The rustic log cabin features a two-story structure with a welcoming wooden facade. A spacious front porch is supported by sturdy columns, allowing for outdoor seating. Surrounding greenery enhances the cabin's natural setting, providing a serene environment.

Cabin in Woodstock

Cozy Log Cabin - Relaxing Retreat w/1pm Checkout

Cozy Cabin has 1pm checkout & no additional cleaning fees. We focus on a comfortable, relaxed, Vermont experience. If you’re looking for peaceful, yet accessible location, we are situated on 15 acres located between Woodstock Village & Killington. There’s fiber WiFi, Hulu w/ +Live TV w/local channels, ESPN+, Disney+, Amazon movies & music, & Netflix. The Rec Room has a pool table, darts, lounge, gym & desk for remote work.

4.98 out of 5 average rating, 226 reviews