Waterfront holiday rentals in Highlands

4.99 out of 5 average rating, 140 reviews

A hammock is suspended between two trees, providing a relaxing spot beside the lake. Vibrant autumn leaves in shades of orange and yellow frame the serene water view, while a wooden dock is visible in the background, inviting guests to enjoy the tranquil setting.

Home in Putnam Valley

Luxury Lake House Sauna 1h From NYC

Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

4.88 out of 5 average rating, 301 reviews

A striking wooden wall showcases a large bank of windows offering panoramic views of Lake Oscawana and surrounding foliage. The vaulted ceiling emphasizes the spaciousness of the room, inviting natural light to fill the space.

Cottage in Putnam Valley

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.

4.89 out of 5 average rating, 210 reviews

A tranquil outdoor deck features two yellow Adirondack chairs facing the Hudson River. The landscape includes distant mountains and a picturesque sunset casting warm colors across the sky, reflecting on the calm water.

Home in Peekskill

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.

4.98 out of 5 average rating, 183 reviews

A serene view of Walton Lake captures a wooden dock extending into calm waters. The setting sun casts a warm glow over the landscape, reflected in the lake. Lush greenery frames the scene, enhancing the tranquil atmosphere.

Cottage in Monroe

Cozy Holiday 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 retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes COMPLIMENTARY Firewood, NO CLEANING/PET FEES🐕

4.97 out of 5 average rating, 103 reviews

A six-person hot tub is positioned on a covered patio, overlooking the tranquil waters of Greenwood Lake. The bubbling water is set against a backdrop of trees and distant homes, creating a serene lakeside atmosphere.

Home in Greenwood Lake

*Waterfront Home w/Hot Tub, Kayaks and Fast Wifi

Waterfront home on Greenwood Lake with a private dock and 6 person hot tub. Situated in a quiet neighborhood and a short walk (1/4 mile) to downtown. Enjoy dinner on the patio, steaks on the grill, and s'mores by the fire pit. A short drive (5 minutes) to the town beach. Professionally cleaned, comfortable, and bright. A perfect place to enjoy Greenwood Lake and the surrounding Hudson Valley area. Nearby hiking, apple picking, and skiing. Fully renovated with top-of-the-line appliances

4.84 out of 5 average rating, 191 reviews

A bright bedroom features two spacious beds covered with white linens and soft blankets. Large windows and skylights fill the room with natural light, showcasing views of greenery outside. Blue curtains frame the windows, and a wicker basket with towels is positioned on a side table.

Home in Monroe

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.

4.96 out of 5 average rating, 484 reviews

A serene view of the Hudson River at sunset, featuring vibrant orange and yellow hues reflected on the calm water. Silhouettes of trees outline the scene, creating a peaceful atmosphere with the distant hills visible against the colorful sky.

Flat in Ossining

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.

4.88 out of 5 average rating, 226 reviews

Flat in Newburgh

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!

4.92 out of 5 average rating, 431 reviews

A spacious living area is depicted, featuring a plush bed and a comfortable sofa. The room includes a wooden TV stand with a flat-screen television and an air conditioning unit in the window. Soft lighting enhances the clean, modern design of the space.

Guest suite in Beacon

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.

4.92 out of 5 average rating, 109 reviews

An aerial view captures a spacious lakefront property surrounded by lush greenery. Trees frame the yard, which gently slopes toward the water. The exterior of the house is clad in light gray, with multiple windows reflecting the natural surroundings. A patio area is visible near the water's edge.

Home in Putnam Valley

Crystal Wave LakeHouse

Make some memories at this renovated, family-friendly Lakefront Oasis! Water activities on your own Peninsula with Lake Frontage on 3 Sides of the Property! Views of the Lake from Almost Every Window! Included is an extra 600 sq ft cottage that has been completely renovated for your enjoyment with a pool table. Utilized as a gaming room & yoga studio! There is a pullout sofa as well for extra guests with a bathroom a few steps away in the main house!

4.98 out of 5 average rating, 120 reviews

The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.

Guest house in Waccabuc

French Guest House in Waccabuc

A private, European-style retreat just 60 minutes from NYC. Set on an eight-acre gated French estate with its own lake, this guest house feels like a mini Versailles with 18th-century statuary, fountains and manicured gardens. Designed by David Easton, it features heated stone floors, a heated towel rack, luxury linens, gold fixtures, fast WiFi, and a private entrance. Minutes from Waccabuc Country Club and the Katonah train station.

4.96 out of 5 average rating, 198 reviews

A dining area features a long wooden table set for meals, with plates arranged on woven placemats. To one side, a bar area displays glassware and coffee equipment. Expansive windows frame scenic lake views, allowing natural light to brighten the space.

Cottage in Putnam Valley

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

Popular amenities for waterfront rentals in Highlands

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.84 out of 5 average rating, 723 reviews

A spacious kitchen and dining area feature light wood cabinetry and modern stainless steel appliances. A wooden dining table is complemented by white chairs, and a window seat provides natural light. Decorative elements include a bowl of fruit at the center of the table.

Flat in Beacon

Top Floor 2BR - Just Renovated!

4.85 out of 5 average rating, 214 reviews

A wooden dock extends into the water, lined with boats gently bobbing on the surface. Lush green hills rise in the background, while a clear blue sky with scattered clouds frames the scene. People are gathered along the dock, enjoying the views.

Flat in Northport

Harbor Studio - Across from historic Northport doc

4.94 out of 5 average rating, 210 reviews

A white dock extends into the calm water, featuring a screened gazebo and several loungers. Lush greenery surrounds the area, highlighting vibrant flowers and shrubs. In the background, a two-story house with large windows overlooks the lake, providing scenic views of the natural surroundings.

Flat in West Milford

Charming Lakeside Retreat

4.93 out of 5 average rating, 138 reviews

A dining area is positioned by large windows offering views of the lake and surrounding landscape. The round table is accompanied by six black chairs, and a light fixture hangs overhead, providing illumination. Sheer curtains allow natural light to fill the space.

Flat in Hopatcong

C’est La Vie Lakefront W/Boat slip available

4.78 out of 5 average rating, 648 reviews

The exterior of a historic stone farmhouse is shown, featuring a vine-covered wall and landscaped garden. Steps lead to the entrance, surrounded by greenery and floral elements, with large windows allowing natural light. The serene outdoor setting reflects the charm of the surrounding countryside.

Flat in High Falls

Art Room at Old Stone Farmhouse

4.92 out of 5 average rating, 302 reviews

A bright living area is presented with minimalistic white furnishings, including a low sectional sofa arranged for relaxed seating. A glass coffee table sits atop a fluffy area rug, accompanied by indoor plants. Natural light fills the space through two large windows.

Flat in Beacon

Lovely 2br Victorian - 5m to train / 3m to main

4.96 out of 5 average rating, 272 reviews

The entrance features a striking red door adorned with a brass plaque labeled 'DeMew Townhouse.' Lush green vines and colorful flower pots with blooming flowers are positioned at the foot of the stairs, enhancing the welcoming atmosphere of the entryway.

Flat in Kingston

DeMew Townhouse in Historic Kingston

4.9 out of 5 average rating, 126 reviews

A circular fire pit area is set on a grassy lawn, surrounded by five Adirondack chairs. Tall trees provide shade, while the river glistens in the background under the warm glow of the sunrise. The scene exudes a sense of tranquility.

Flat in Wallkill

Waterfront Gem: 1BR w/Private Balcony & Serenity

Waterfront house rentals

4.93 out of 5 average rating, 121 reviews

A serene view of Squantz Pond is framed by lush greenery, with vibrant trees and neatly trimmed grass in the foreground. The tranquil water reflects the sky, creating a peaceful atmosphere, while a private dock is visible along the water's edge.

Home in New Fairfield

Beautiful Lakefront Retreat with Private Dock

4.97 out of 5 average rating, 197 reviews

A sunlit deck overlooks the serene lake, featuring a glass-top table and comfortable seating. Flower pots add color, while the gentle waves can be seen against the wooden dock. The expansive waterway and surrounding hills create a peaceful backdrop.

Home in Sterling Forest

The Best Lake House! *Ask About Boat Use Promo*

4.94 out of 5 average rating, 322 reviews

A charming farmhouse exterior is presented, featuring a well-maintained porch with seating. The facade showcases a combination of horizontal and vertical siding, complemented by a sloped roof. Lush greenery surrounds the property, enhancing the serene atmosphere of the rural setting.

Home in Kingston

Hudson Valley Hygge House~ comfort in the country!

4.96 out of 5 average rating, 113 reviews

Home in Danbury

Lakeview Estate - Chef's Kitchen - NYC Getaway

4.96 out of 5 average rating, 389 reviews

A cabin with a red metal roof is nestled among tall trees beside a gently flowing creek. The structure features large windows, allowing natural light to fill the interior while offering views of the surrounding greenery.

Home in Livingston Manor

Modern creekside cabin in the Catskills

4.91 out of 5 average rating, 735 reviews

The exterior of the cottage is shown, featuring rich wood paneling and large glass doors. A stone pathway leads to a charming seating area, which includes a decorative bench. Lush greenery surrounds the property, enhancing the natural environment.

Home in Woodstock

Dutch Touch Woodstock Cottage

4.96 out of 5 average rating, 785 reviews

A spacious living area showcases rich wooden paneling and high, sloped ceilings. A large leather sectional is arranged around a central wooden coffee table. Natural light streams through multiple windows, with a stylish fan overhead adding to the cozy ambiance.

Home in New Paltz

Victorian Haven

4.94 out of 5 average rating, 326 reviews

The living room features large windows offering views of the river and surrounding trees. A blue sofa and a beige tufted couch are positioned around a wooden coffee table, while a colorful area rug adds warmth to the space. Bright yellow walls enhance the inviting atmosphere.

Home in New Paltz

Welcome to The Boathouse! Waterfront/Boats/Hot tub

Waterfront apartment rentals

Private room in West New York

A panoramic view of the New York City skyline is captured during golden hour. The skyline reflects sunlight over the water, creating a serene atmosphere. In the foreground, residential buildings line the shore, while a road curves along the riverbank.

4.89 out of 5 average rating, 57 reviews

Private bed with views of NYC

Apartment in West New York

4.89 out of 5 average rating, 28 reviews

Modern, Private Studio Apt. - 15 Min. from NYC

A spacious sleeping area features a tufted white bed with dark bedding, complemented by two decorative pillows. A tall, framed mirror stands beside a clear side table. The wall behind is adorned with a patterned wallpaper, and warm wooden flooring adds to the inviting space.

Apartment in Yonkers

Hudson Valley Cottage Apartment

Apartment in Vernon Township

An entrance is seen with large glass doors leading into the building. A stone wall features a decorative holiday wreath, and planters with greenery are placed on either side of the walkway. The path is paved and surrounded by a landscaped area.

4.85 out of 5 average rating, 105 reviews

Courtyard Overlook @ Spa Owners Residential Condo

Private room in West New York

5 out of 5 average rating, 7 reviews

Lovely 1 BR -15 mins from Times Square

4.81 out of 5 average rating, 90 reviews

The spacious living area features a gas fireplace surrounded by comfortable seating, including leather sofas and armchairs. Large windows allow natural light to illuminate the space, while a dining area with vibrant chairs is visible in the background, contributing to a welcoming and cozy environment.

Apartment in vernon

Mtn Creek Ski Resort Hot Tub Shuttle 09-23M