Beachfront vacation rentals in Dutchess County

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Dutchess County

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The exterior of a two-story house is featured, surrounded by autumn foliage. A gravel driveway leads to the entrance, with vibrant flower beds and a porch extending across the front. The house overlooks the serene waters of the lake, adding a tranquil backdrop.

Your own private lake + beach, boats & game room!

Lakeside estate in Berkshire foothills 1½ hours north of NYC. Unique 4-season vacation destination includes use of estate-owned lake. Spacious, comfortable areas for family gatherings, groups of friends, or small to medium-sized weddings/events (contact owner for event pricing & info on extra sleeping accommodations in carriage house apt). Max 2 dogs ($20/day pet fee charged when reservation confirmed). Memorial Day week-Labor Day week is 7 day min, Saturday-Saturday, otherwise min 3 day rental.

4.81 out of 5 average rating, 27 reviews

Superhost

Home in Rhinebeck

Private Lakefront Bungalow

Outside Rhinebeck, renovated sunny 2 bedroom bungalow on Silver Lake. Private lakefront sandy beach, dock, canoe, kayak, paddle board + outdoor fire pit. Great fishing + swimming. Smart TV, projector w apple tv with woodstove. Newly remodeled eatin kitchen. The house includes to private 2 queen bedrooms and additional sleeping loft with a full bed. Large master bedroom with vaulted ceilings, private bath, and french doors leading out to deck with lake view. Additional outhouse workspace.

4.83 out of 5 average rating, 312 reviews

A spacious wooden deck is surrounded by trees and overlooks the lake. Soft lighting from string lights creates a warm ambiance. A round dining table with several chairs is placed in the center, offering a comfortable space for outdoor meals.

Home in Pine Plains

Designer Lakefront house, a hiking-ski retreat.

Lakefront property at its finest, recently renovated designer house. Beautiful Twin Island Lake. The peace and tranquillity of a non-motorboat lake is something to truly love & enjoy. Enjoy kayaking or just resting on the large deck that overlooks the beautiful Lake; our family summer home and we put much care into ints maintenance; You will find everything in the house of high quality. A remote sanctuary minutes from the town, this home delivers the much-needed 'Good Life'.

4.74 out of 5 average rating, 121 reviews

Guest favorite

A serene lakeside view is captured at sunset, with vibrant pink and purple hues reflecting over the calm water. Silhouetted trees frame the scene, and distant hills provide a tranquil backdrop to the picturesque landscape.

Home in Pine Plains

Twin Island Lake House • Hot Tub

Hudson Valley’s best kept secret. Built in 2018, perched on 4 acres. 3 bedrooms 2 full baths include master suite with private bathroom. Open concept kitchen/living room. A perfect getaway to relax and recharge in our year round 6 person hot tub. Amazing views and sunsets over the lake and mountains. Great area for hiking, fishing, kayaking, canoeing and bird watching. 16 miles to the center of Rhinebeck. Explore the local farms, restaurants, distilleries and wineries.

4.97 out of 5 average rating, 141 reviews

Guest favorite

Apartment in Saugerties

Charming Creekfront | Sauna• Hot Tub • Fire Pit

FALL IN THE CATSKILLS — ESOPUS CREEK & MOUNTAIN VIEWS Experience fall in the Catskills from this 3BR/1BA creekside retreat with beautiful mountain, water and foliage views. Soak in the hot tub, unwind in the sauna, gather around the fire pit, or kayak and fish on Esopus Creek. Enjoy a water-facing balcony, fully equipped kitchen, 75-inch Smart TV, 3,000 arcade games, high-speed WiFi, and a prime Saugerties location within walking distance to restaurants and shops.

5.0 out of 5 average rating, 6 reviews

Top guest favorite

An aerial view showcases a lakefront cottage with a warm-toned roof, surrounded by lush greenery. Two blue kayaks sit on the water, while a stone patio features a dining area. A fire pit adds to the outdoor space, blending with a wooden boat dock.

Cottage in Livingston

Waterlily Lakehouse - Modern+Waterfront+Retreat

The Waterlily House is a Lakefront cottage at the North Twin Lakes in Livingston, NY, located just 2 hours from NYC. The lakefront cottage has been designed and decorated in a Frandinavian Style (Parisian chic and Scandinavian minimalism ). This chic 4 bedroom, 3 bath home, which can sleep up to 8 people, has been designed with an eye for detail, style, and relaxation. Follow us on IG @waterlilylakehouse for any last-minute cancellations/openings

4.97 out of 5 average rating, 145 reviews

Top guest favorite

The restored a-frame stone cottage is nestled among trees, featuring a wooden deck and stone steps leading to the entrance. A propane grill is positioned on the deck, with a tranquil wooded backdrop showcasing the colors of nature.

Cottage in Pawling

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

4.99 out of 5 average rating, 185 reviews

Guest favorite

A wooden dock extends over the lake, surrounded by vibrant green lily pads and patches of aquatic plants. The serene water reflects a clear blue sky, while trees line the distant shore, creating a peaceful natural setting.

Guesthouse in Rhinebeck

Enjoy life on a lake, 90 mn from NYC

Lake access. Escape the city for a relaxing weekend on a perfect lake with incredible views, swimming and fishing (weather permitting) and ice skating in the winter. Only minutes from the village of Rhinebeck, close to Omega institute, and only 45mn from Catamount and Belleayre ski resorts. Modern guest house in a private artist estate with its own private parking and entrance.

4.89 out of 5 average rating, 79 reviews

Guest favorite