Beachfront holiday rentals in Dutchess County

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Dutchess County

Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

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Superhost

Home in Wingdale

4.9 out of 5 average rating, 21 reviews

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.

Home in Rhinebeck

4.83 out of 5 average rating, 280 reviews

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.

Home in Pine Plains

4.77 out of 5 average rating, 101 reviews

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'.

Guest favourite

Home in Pine Plains

4.98 out of 5 average rating, 131 reviews

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.

Guest suite in Carmel-by-the-Sea

4.95 out of 5 average rating, 97 reviews

Secluded Hudson Valley Retreat with Private Lake

Swim, fish, and canoe in the secluded private, natural spring-fed lake. Watch great blue herons, river otters, beavers, fox, and red tail hawks in their natural habitat. Fish for small & large mouth bass. Barbeque and dine right outside your suite. Complete your evening with a campfire in the quiet, serene, and crowd-free environment. RELAX. You'll be hidden deep in the woods with all the essential amenities just over a mile away. NO CHILDREN UNDER 12 YEARS OLD!

Home in Holmes

Peaceful Whaley Lake House - Holmes NY

Come visit this spacious and warm home overlooking beautiful Whaley Lake in Dutchess County, NY. Enjoy the company of friends and family and the picturesque view from deck overlooking the lake or movie and game night in the open family room. Kayak the lake and see the sights of the scenic Mid-Hudson Valley. Short trips to state parks and scenic upstate New York. Relax and enjoy the cozy and comfortable accommodations and the quiet beauty of lake life.

Superhost

Flat in Saugerties

5 out of 5 average rating, 4 reviews

Charming Creekfront | Sauna • Tub • Fire Pit

Welcome to Upstate Waterfronts! Looking for a restorative Upstate getaway? This Creekside gem has you covered. - HOT TUB - SAUNA - 3 bedrooms/ 1 full bathroom - Fully equipped kitchen & high-end amenities - Private creek access - including kayaks/vests/paddles - Stunning creek views - including a water facing balcony - 3,000 Arcade games, 75'' Smart TV, endless board games - High-speed WiFi - Prime location - walkable to town/restaurants/shops/beach

Guest favourite

Cottage in Livingston

4.98 out of 5 average rating, 102 reviews

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

Guest favourite

Cottage in Pawling

4.99 out of 5 average rating, 140 reviews

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.

Guest favourite

Island in Pine Plains

4.94 out of 5 average rating, 93 reviews

Private Island on Twin Island Lake

Embark on an off-grid luxury glamping adventure in the heart of Hudson Valley, discover one of Twin Island Lake’s private island with 360 degree views.. Reconnect with yourselves and nature in a Safari style tent furnished with a queen size bed. 13x10 gazebo with outdoor amenities. Park on the mainland next to the dock where a canoe awaits your arrival. This sweet escape is a once in a lifetime experience you will remember forever.

Guest house in Rhinebeck

4.87 out of 5 average rating, 70 reviews

Enjoy life on a lake, 90 mn from NYC privacy

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.