Waterfront vacation rentals in Highlands

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Highlands

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

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Guest favorite

Home in Greenwood Lake

4.98 out of 5 average rating, 100 reviews

Your lakefront castle awaits you …

Imagine a castle on a lake. Welcome to Castlebrook, a luxurious Lakefront home on Greenwood Lake, NY. This exquisitely appointed home has sweeping vistas of the lake yet is private enough for a relaxing getaway. 3 large bedrooms, 3 full baths, boat slip, jet ski dock, outdoor grill and firepit, meticulously manicured grounds await you just an hour from NYC, 15 minutes from Tuxedo train, 30 minutes from Legoland. Spacious entertaining areas, all with sweeping views of the lake. True luxury.

Guest favorite

Farm stay in Montgomery

4.93 out of 5 average rating, 412 reviews

The Step by 127 Cabin Co.

Looking for a cozy escape from the winter hustle or maybe looking to celebrate a special occasion? The Step is a charming A-Frame designed for a simple but memorable stay. Snuggle up with a warm drink by the fire or enjoy a peaceful night under the stars. Tucked away on serene farmland, it’s just 3 minutes from town, where you can savor delicious local restaurants and visit cute cafes and shops. Experience the tranquility of nature while staying off the grid. *Please note, there’s no shower.

Guest favorite

Cottage in Putnam Valley

4.88 out of 5 average rating, 249 reviews

Lakefront Cottage near Hudson Valley

Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

Guest favorite

Cottage in Monroe

4.99 out of 5 average rating, 144 reviews

Cozy Lake Cabin

Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets on the covered porch & deck. Fish, & look for bald eagles🦅 Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has abundant retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes Free Firewood, NO CLEANING/PET FEES🐕

Guest favorite

Home in Greenwood Lake

4.96 out of 5 average rating, 233 reviews

Stylish Lakeside Chalet with Hot Tub

Welcome to Greenwood Lakeside Chalet, an all-season waterfront retreat on beautiful Greenwood Lake (just over an hour from NYC) surrounded by the Sterling Forest and the Appalachian Trail Corridor. No car? No problem! Conveniently located just steps away from an express bus stop with regular service to/from Port Authority. Boating, Hiking, Fishing, Skiing, Breweries, Wineries, Apple Picking, Waterfront Restaurants, Shopping, Historical Sites, Golf - all nearby (or right in the backyard).

Guest favorite

Home in Monroe

4.88 out of 5 average rating, 118 reviews

Sunlit & Peaceful. Hot Tub. Monroe. 1hr fr NYC.

Welcome to our cozy retreat in Monroe, NY where relaxation awaits you. Our charming Home is bathed in natural sunlight, thanks to numerous windows and skylights, creating a warm and inviting ambiance. Nature lovers can explore the scenic Heritage Trail, perfect for leisurely walks or bike rides. If shopping is on your agenda, the Premium Outlets at Woodbury Commons are just a short drive away. For family fun, Legoland is a nearby attraction, promising excitement, and joy for all ages.

Guest favorite

Rental unit in Ossining

4.95 out of 5 average rating, 384 reviews

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

Guest favorite

Rental unit in Newburgh

4.85 out of 5 average rating, 154 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Superhost

Home in Peekskill

4.9 out of 5 average rating, 172 reviews

The Peekskill RiverView House

The Peekskill RiverView House A fully renovated dream house overlooking the historic Peekskill Bay. This 3 bedroom 3.5 bath designer house is a 5 minute walk to the train station as well as the historic downtown. It’s truly the gateway to the Hudson Valley along with having the walkable access to culture, hiking, biking, culinary, spa, and entertainment activities within City limits. Expansive decks on all 3 floors with spectacular Hudson River views from every room.

Guest favorite

Cottage in Walden

4.96 out of 5 average rating, 103 reviews

Cute, Cozy, Lakefront cottage

Cute, cozy lakefront cottage on private lake. Deck with an unobstructed view of the lake. Stunning sunrises, pinewood floors in bedroom/living room/kitchen. Queen size bed in bedroom. Situated on the same lot as owner occupied main house. Quiet, residential area. Near wineries, breweries, hiking. WIFI. No TV. Unfortunately, due to severe pet allergies I am unable to host any kind of animals including emotional support and service dogs and cats of any kind.

Guest favorite

Home in Wappingers Falls

4.93 out of 5 average rating, 165 reviews

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. Be our guest at our beautiful home located on the widest part of the Hudson River. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door.

Guest favorite

Cottage in Putnam Valley

4.95 out of 5 average rating, 135 reviews

Private Lake House 1 Hour to NYC & Near Westpoint

Escape to this private lake cottage. Just 1h drive from NYC, near lots of skiing & hiking Thunder Ridge (30mi) Mt Peter (30mi) Victor Constant (20mi) Campgaw Mountain (40mi) Enjoy panoramic lake views, 86in TV, ample board games, 5-jet shower, and indoor jetted Jacuzzi tub. Short drive to Bear Mountain & West Point. Legoland is 45 min away Pets are welcome! WiFi is extremely fast and we have free electric car charging