Waterfront holiday rentals in Dutchess County

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Dutchess County

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

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Guest favourite

Home in Carmel Hamlet

4.92 out of 5 average rating, 173 reviews

Lux Bungalow on the Lake

Beautiful, light flooded, waterfront home 1 hour from New York City. The 2 bedroom home is on picturesque Lake Carmel. Wake up, eat, sleep and relax to the tranquil view of the glistening water - truly an oasis! Take in a sunset while eating a meal at home, explore the shops and restaurants in a cute nearby town, take a walk around the lake, read a book by the cozy fireplace, hike, cook, kayak, ski, or just sit and enjoy. Centrally located close to Hudson Valley, Westchester and Connecticut.

Guest favourite

Home in Lake Katrine

4.95 out of 5 average rating, 110 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Guest favourite

Cabin in New Milford

4.95 out of 5 average rating, 186 reviews

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Guest favourite

Home in Kingston

4.97 out of 5 average rating, 272 reviews

DeMew House in Historic Kingston

PRIVATE, ELEGANT ONE KING BEDROOM HOME! DeMew House is an exclusive renovated 1850s brick home, a block from the historic Kingston waterfront. Enjoy total privacy in an elegant, transitional two-story home with an open floor plan that is inviting, warm and intimate. The home, across from a marina, has a king bedroom, a pull-out sofa bed, an en suite bathroom with two-person shower and double vanity. A full kitchen, ac, private driveway and gazebo frame this discerning getaway...

Guest favourite

Guest suite in Beacon

4.92 out of 5 average rating, 389 reviews

Creekside Beacon—Go Car-Free!—Steps to Hiking/Main

(Please click the "Show more" button below to expand & read full listing BEFORE booking! You'll see why I ask at end!) RECENTLY RENOVATED! Wake up next to a burbling creek in this immaculately clean full-floor apartment filled with midcentury design and modern tech. Steps to Main St, Roundhouse, and so much hiking. Perfect for a car-free escape. Easy access to Metro-North train, Dia, & quick walk to Mt Beacon hiking. Also near: Storm King, Breakneck Ridge, West Point.

Guest favourite

Home in Pine Plains

4.98 out of 5 average rating, 122 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 hiking, fishing, kayaking, canoeing and bird watching. 16 miles to the center of Rhinebeck. Explore the local farms, restaurants, distilleries and wineries.

Guest favourite

Flat in Saugerties

4.86 out of 5 average rating, 148 reviews

Saugerties Marina Peaceful Setting On the Water

Comfort in the Catskills! Enjoy an affordable picturesque location! Newly renovated kitchen with all the comforts of home. We are minutes from HITS, Woodstock, Rhinebeck and a short distance to ski and hiking areas. Pets welcome, arrange prior to booking for our policies regarding pets. This home is the perfect peaceful getaway for boaters and water lovers. This charming 2 bedroom w/ full bath apartment is located on a dead end road and has off street parking.

Guest favourite

Home in Saugerties

4.93 out of 5 average rating, 140 reviews

Upstate Waterfront Saugerties Retreat-Near HITS

Serene riverfront home, just outside the Village of Saugerties with strong Wifi for easy work-from-home. You can swim, canoe, fish on the banks of the Esopus direct from your own home. Bright and stylish space with clean aesthetic, direct water access with lovely views across the Esopus to a protected preserve - ideal for dinners on the deck in Summer or Fall. Or cozy up by the fireplace in Winter after skiing at Hunter, and binge on movies on the large TV.

Guest favourite

Cottage in Pawling

4.98 out of 5 average rating, 111 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

Cottage in Port Ewen

4.99 out of 5 average rating, 143 reviews

Swan Cottage with Expansive Hudson River Views

The Swan Cottage was built in 1923 and was fully renovated in 2020. The idyllic location, on a bluff overlooking the Hudson River, is the perfect perch to relax and get away from it all. The front porch is a nice spot to have a cup of coffee and watch the sailboats on the river, while the huge wraparound porch affords terrific views of the river as well as the forest that gives this home a feeling of being high in the tree tops.

Guest favourite

Guest house in Ulster Park

4.99 out of 5 average rating, 409 reviews

Escape to a Sleek, Serene Studio on the Riverbank

Dine on the private, covered veranda as eagles swoop and fish jump across the water. Enjoy the view through floor-to-ceiling glass windows for magical views from bed. Crisp, calm blues, grays, and silvers set the tranquil scene at this modern hideaway. The well-appointed studio is perfectly situated to offer you amazing river views and privacy. It is extremely quiet and convenient to nearby attractions.

Guest favourite

Campsite in Lake Katrine

4.96 out of 5 average rating, 167 reviews

Private Waterfront Winter Camping Experience

PRIVATE SINGLE CAMPSITE. OWNER OPERATED. This quaint little tent and private deck are nestled among the trees on the banks of the Esopus Creek in a great little neighborhood! A way to get back to nature without truly leaving it all behind. A one of a kind private waterfront escape with a fire pit & electric! WATER ACCESS AND KAYAKS NOW AVAILABLE! Enjoy a 2.5 mile stretch of the Esopus creek!