Waterfront vacation rentals in Philipstown

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Philipstown

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

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Guest favorite

Home in Carmel Hamlet

4.92 out of 5 average rating, 131 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.

Nov 26 – Dec 3

ﺩ.ﺇ1,600 per night

Guest favorite

Home in Stormville

4.94 out of 5 average rating, 156 reviews

Private Hudson Valley Country Retreat

Beautiful 1930s house set on 18 private acres of land overlooking a private lake. Immaculately landscaped surrounding area with koi and gold fish pond with a waterfall, gazebo, hammock and most importantly untouched nature. Very private! Enjoy your morning coffee or tea in the outdoor covered patio overlooking the property, wine and dine under the pergola, enjoy the fire pit or wood burning fireplace on a chilly evening. Serenity and relaxation at its best! Pond dock coming up in Spring of 2021

Dec 29 – Jan 5

ﺩ.ﺇ3,005 per night

Guest favorite

Farm stay in Montgomery

4.93 out of 5 average rating, 346 reviews

The Step by 127 Cabin Co.

Looking for a night out to relax and escape the hustle and bustle? The Step is a small custom built A-Frame designed for those looking for a simple & memorable stay. Whether you are looking for a quiet night under the stars or a space to unwind while being off the grid, The Step is a great place for you to experience all that nature has to offer. The cabin is private & secluded located on farmland. Just 3 minutes from town with great local restaurants, pickle ball, & more *Please Note No Shower

Sep 25 – Oct 2

ﺩ.ﺇ710 per night

Superhost

Cottage in Putnam Valley

4.89 out of 5 average rating, 216 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.

Oct 10 – 17

ﺩ.ﺇ1,427 per night

Guest favorite

Home in Putnam Valley

4.96 out of 5 average rating, 102 reviews

Lake Cottage Near Sleepy Hollow, Westpoint & NYC

Escape to this private lakeside cottage. Just 1h drive from NYC near lots of skiing: 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 The cottage can accommodate up to 10 guests and is family-friendly. Pets are welcome! WiFi is extremely fast and we have free electric car charging.

Jul 29 – Aug 5

ﺩ.ﺇ2,679 per night

Guest favorite

Cabin in Wurtsboro

4.98 out of 5 average rating, 208 reviews

Spring Spa on a Cascading Brook - The Water House

The brook flows through an evergreen forest creating a nourishing environment and the perfect setting for a relaxing and rejuvenating spa retreat. The living/dining room, hot tub/deck, and fire pit are set overlooking the cascading brook, ideal for entertaining, meditating or simply as an enjoyable natural muse. The soft, cozy and elegantly vintage styled interior is illuminated and warmed with central heating, ambient lighting and a home surround sound entertainment system with karaoke.

Aug 18 – 25

ﺩ.ﺇ1,311 per night

Superhost

Apartment in Newburgh

4.84 out of 5 average rating, 118 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!

Aug 15 – 22

ﺩ.ﺇ562 per night

Guest favorite

Guest suite in Beacon

4.91 out of 5 average rating, 361 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.

Jun 12 – 19

ﺩ.ﺇ965 per night

Superhost

Home in Peekskill

4.9 out of 5 average rating, 154 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.

Feb 28 – Mar 7

ﺩ.ﺇ1,427 per night

Superhost

Apartment in Beacon

4.83 out of 5 average rating, 556 reviews

Top Floor 2BR - Just Renovated!

This 2BR apartment is the entire top floor of an 1870 brick house. Extensively renovated in 2021 - all new kitchen, major updates to the bathroom, new paint, furniture and decor throughout. Directly behind the house is Fishkill Creek and abandoned railway tracks (you can walk to Main St on them in 10 minutes - or walk on the sidewalk if you prefer). It's a perfect space for up to 4 people visiting Beacon and the beautiful Hudson Valley. [LI Zoning: Fully Permitted]

Sep 28 – Oct 5

ﺩ.ﺇ928 per night

Guest favorite

Apartment in Ossining

4.94 out of 5 average rating, 309 reviews

Hudson River Peaceful Getaway

Self check-in and private entrance. Parking for two cars. Peaceful apartment on the Hudson River. Train to NYC (Scarborough Station) is an 8 minute walk through historic neighborhood. Arcadian Mall (Grocery store, Starbucks, etc) 5 minute walk. Rivers views from inside and from three patios (1 on entrance side, 2 on River side). We only allow declawed cats because they can scratch and damage our expensive furniture and carpets. Most house trained dogs are welcome :)

Nov 15 – 22

ﺩ.ﺇ1,036 per night

Guest favorite

Home in Wappingers Falls

4.97 out of 5 average rating, 108 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.

Aug 29 – Sep 3

ﺩ.ﺇ613 per night