
Waterfront holiday rentals in Highlands
Find and book unique waterfront rentals on Airbnb
Quick stats about waterfront rentals in Highlands

Total holiday rentals
Explore 10 holiday rentals in Highlands

Nightly prices starting at
Highlands holiday rentals start at £74 per night before taxes and fees

Verified guest reviews
Over 1,080 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Wifi availability
10 of Highlands holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Highlands rentals

4.9 Average rating
Highlands stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated waterfront rentals in Highlands
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!
Kitchen & Basement Newly Finished!! Enjoy your very own LAKEFRONT WONDERLAND with a trove of amenities and space to WFH with fast internet! A perfectly manicured landscape with a Goldilocks-sized pool. The lawn leads to your very own private dock and brick patio, containing a fire-pit. Swim to your heart's content in the pool or in the lake. Soak in the hot tub. Paddle in our canoe or kayak and try snagging some brown trout. Plenty of room for a large extended family or a group of friends.
4.96 out of 5 average rating, 141 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.
4.88 out of 5 average rating, 329 reviews
Cozy Lake Cottage
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 in any temps from inside or out, or coffee in the tree hut! Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes COMPLIMENTARY Firewood, NO CLEANING/PET FEES🐕
4.99 out of 5 average rating, 205 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, the train is loud, 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.
4.89 out of 5 average rating, 225 reviews
Waterfront Lake House
Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.
4.94 out of 5 average rating, 138 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!
4.89 out of 5 average rating, 274 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. $19 cleaning with or without pets.
4.96 out of 5 average rating, 557 reviews
Top Floor 2BR
Full-floor 2BR in historic 1870 brick building with creek & Mt. Beacon views, shared backyard oasis (covered lounges, fire pit, seasonal stream). Walk the scenic abandoned railway tracks alongside Fishkill Creek to Main St and the Roundhouse waterfall in 10 min. Interior and exterior by award winning Hudson Valley designer Simone Eisold. Two off-street parking spots. Ask about upgrading to the private patio with treetop hot tub & Mt. Beacon vistas! [Permit: 2024-0027-STR]
4.85 out of 5 average rating, 781 reviews
The Cove Cabin
An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two two-person kayaks are available for use from May 1 to November 1.
4.96 out of 5 average rating, 458 reviews
Hudson Valley Hygge House~ comfort in the country!
Experience the cozy charm of hygge at the farmhouse by a tranquil pond in Rosendale. Nestled in the Hudson Valley, just minutes from Kingston, Stone Ridge, and High Falls—and only 90 miles from NYC—this retreat offers pure serenity. Located on a quiet country road, enjoy the sounds of birdsong, evening frog lullabies, and a gas fireplace for a cozy winter escape. Set on over 3 acres, nature abounds here. Come and enjoy all the Hudson Valley has to offer!
4.95 out of 5 average rating, 370 reviews
Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC
Escape to our modern, year-round lakeside paradise on Greenwood Lake, just 1 hour from NYC. This bright, airy home offers stunning lake views, a private dock, and a sandy beach area. Perfect for families or couples, enjoy seasonal activities from swimming and kayaking in the summer to skiing just 10 minutes away in the winter. Relax by one of two fireplaces or on the spacious deck. A tranquil retreat for relaxation and adventure. Permit N. 23-225
4.97 out of 5 average rating, 114 reviews
Hudson Valley Lakefront Cottage | Nature Escape
Escape to this tranquil, lakefront cottage in the Hudson Valley. Enjoy stunning lake and cascading creek views, kayaks, paddleboards, a firepit with a steady supply of firewood for cozy evening fires, two Weber grills, and an on-site Level 2 EV charger. Ideal for couples, small groups, or intimate gatherings seeking a peaceful retreat surrounded by nature.
4.96 out of 5 average rating, 120 reviewsPopular amenities for waterfront rentals in Highlands
Waterfront apartment rentals

Art Room at Old Stone Farmhouse
4.78 out of 5 average rating, 715 reviews
Lovely 2br Victorian - 5m to train / 3m to main
4.92 out of 5 average rating, 334 reviews
Charming Lakeside Retreat
4.93 out of 5 average rating, 233 reviews
The Bennett Cabin
4.86 out of 5 average rating, 119 reviews
Escape to a Sleek, Serene Studio on the Riverbank
4.99 out of 5 average rating, 461 reviews
C'est La Vie Lakefront W/Optional boat slip
4.95 out of 5 average rating, 207 reviews
Lovely 1 bedroom apt. with free parking in Rondout
4.98 out of 5 average rating, 233 reviews
Seabreeze at the beach, west beach stamford, Ct
4.94 out of 5 average rating, 101 reviewsWaterfront house rentals

4Br Mountain Brook House on 130 acres w/ trails
4.88 out of 5 average rating, 220 reviews
Riverfront Stone Cottage Private/ hot tub/ boats
4.91 out of 5 average rating, 303 reviews
Slate Cabin - Stylish Country Escape x Rhinebeck
4.98 out of 5 average rating, 130 reviews
Stylish Lakeside Cottage with Hot Tub
4.96 out of 5 average rating, 327 reviews
Wake up to this view everyday! Relax & recharge!
5.0 out of 5 average rating, 169 reviews
Lux Bungalow on the Lake
4.93 out of 5 average rating, 230 reviews
Beautiful Lakefront Retreat with Private Dock
4.93 out of 5 average rating, 132 reviews
Scenic River View Escape | New Paltz
4.88 out of 5 average rating, 238 reviewsWaterfront apartment rentals

Courtyard Overlook @ Spa Owners Residential Condo
4.81 out of 5 average rating, 112 reviews
Luxury Romantic Hideaway
4.96 out of 5 average rating, 79 reviews
Walk to Waterpark Pool Hot Tub 09-23M
4.81 out of 5 average rating, 100 reviews
Little Getaway at the Black Creek Sanctuary
4.99 out of 5 average rating, 95 reviews
Tranquility on the Lake!
5.0 out of 5 average rating, 15 reviews
NYC Riverfront White Marble Sanctuary Free Parking
4.67 out of 5 average rating, 209 reviews
Sunset River Views Condo w balcony, >1100 SF
3.88 out of 5 average rating, 8 reviews
Hudson Valley Cottage Apartment
Destinations to explore
- New York Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Boston Holiday rentals
- Ocean City Holiday rentals
- Niagara Falls Holiday rentals
- Jersey City Holiday rentals
- Portland Holiday rentals
- Newark Holiday rentals
- Baltimore Holiday rentals
- Atlantic City Holiday rentals
- Chalet rentals Highlands
- Rentals with pools Highlands
- Rentals with breakfast Highlands
- Pet-friendly rentals Highlands
- House rentals Highlands
- Cottage rentals Highlands
- Family-friendly rentals Highlands
- Flat rentals Highlands
- Hotel rooms Highlands
- Cabin rentals Highlands
- Waterfront rentals Orange County
- Waterfront rentals New York
- Waterfront rentals United States
- Times Square
- Central Park Zoo
- Mountain Creek Resort
- Columbia University
- Yankee Stadium
- American Dream
- MetLife Stadium
- New York City Center
- Rockefeller Center
- United Nations Headquarters
- Empire State Building
- Bear Mountain State Park
- Bryant Park
- Barclays Center
- Citi Field
- Statue of Liberty
- Grand Central Terminal
- Minnewaska State Park Preserve
- Brooklyn Bridge
- Radio City Music Hall
- Astoria Park
- Fairfield Beach
- Thunder Ridge Ski Area
- The Metropolitan Museum of Art





