Beachfront vacation 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 Rhinebeck

4.84 out of 5 average rating, 238 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.

Jun. 10 – 17

$643 CAD per night

Guest favourite

Home in Wingdale

5.0 out of 5 average rating, 6 reviews

Your 4-Season Private Lakeside Paradise Awaits

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 and info on extra event sleeping accommodations in carriage house apt). Max 2 dogs ($20/day pet fee charged when reservation confirmed). Summer rentals min 7 days, Friday-Friday, otherwise min 3 day rental.

Nov. 3 – 10

$1,013 CAD per night

Superhost

Home in Pine Plains

4.74 out of 5 average rating, 77 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'.

Oct. 7 – 14

$374 CAD per night

Guest favourite

Guest suite in Carmel

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!

Jul. 9 – 16

$292 CAD per night

Guest favourite

Home in Pine Plains

4.98 out of 5 average rating, 110 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.

Oct. 4 – 11

$526 CAD per night

Superhost

Home in Cold Spring

Relaxing Lake Retreat in Cold Spring

Welcome to Valhalla Highlands, a peaceful retreat located just one hour from NYC and only ten minutes from Cold Spring village. Enjoy the quiet dirt roads, beautiful trails, and tennis courts, as well as the gorgeous Lake Valhalla with beach, dock, and non-motorized boat access. Our newly renovated home is located within walking distance from the lake, and offers several comfortable rooms plus a private patio and BBQ for your use. Join us for a weekend getaway!

Aug. 27 – Sep. 3

$770 CAD per night

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.

Aug. 22 – 29

$966 CAD per night

Guest favourite

Cottage in Livingston

4.97 out of 5 average rating, 38 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

Jul. 23 – 30

$1,075 CAD per night

Guest favourite

Cottage in Pawling

5.0 out of 5 average rating, 62 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.

Apr. 12 – 19

$537 CAD per night

Guest favourite

Island in Pine Plains

4.93 out of 5 average rating, 80 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.

Dec. 22 – 29

$448 CAD per night

Superhost

Home in New Fairfield

4.77 out of 5 average rating, 44 reviews

Cheerful home with amazing lake view.

Forget your worries in this spacious and serene space. Offering tons of privacy. The house sits on a hill over seeing the amazing lake. Where you can enjoy barbecuing with friends, family and an entertaining room. My place is close to supermarkets, shopping malls and restaurants within a reasonable driving distance. Pack and play is available upon request. My place is not wheelchair accessible.

Mar. 26 – Apr. 2

$336 CAD per night