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Waterfront holiday rentals in Philipstown

Find and book unique waterfront rentals on Airbnb

Quick stats about waterfront rentals in Philipstown

  • Total holiday rentals

    Explore 40 holiday rentals in Philipstown

  • Nightly prices starting at

    Philipstown holiday rentals start at €52 per night before taxes and fees

  • Verified guest reviews

    Over 2,930 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Philipstown holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Philipstown rentals

  • 4.9 Average rating

    Philipstown stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated waterfront rentals in Philipstown

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

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Top guest favourite
A dining area is shown with a round wooden table at the center, adorned with a vase of flowers. Large glass windows frame a serene lakeside view, with blooming flowers in the foreground and lush greenery. Soft sunlight reflects off the water, creating a tranquil atmosphere.
Home in Carmel Hamlet

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.

4.93 out of 5 average rating, 231 reviews
Guest favourite
An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.
Home in New Paltz

Scenic River View Escape | New Paltz

Unwind in nature at this scenic New Paltz escape, located on a serene riverbank with spectacular views. Large porch and private backyard are perfect for relaxation and stargazing. Recently renovated, the house blends modern amenities with a tranquil atmosphere. Thoughtfully designed, it features a cozy fireplace, large smart TV, and fully equipped kitchen. Explore nearby hiking trails, waterfalls, and Minnewaska State Park, or relax in the hot tub. Ideal for couples, families, and remote workers

4.88 out of 5 average rating, 243 reviews
Top guest favourite
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

4.99 out of 5 average rating, 191 reviews
Top guest favourite
A spacious outdoor area features a modern pool surrounded by wooden decking. Lounge chairs are positioned under large umbrellas, providing shade. The two-story home is visible in the background, showcasing large windows that enhance natural light.
Home in Putnam Valley

Heated Pool, Ultra Modern Home 5B, hot tub, sauna

Secluded, luxurious 5Br/3.5Bth home an hour from NYC, nested on a 9-acre property with the Appalachian trail running through. Modern-rustic design, floor-to-ceiling windows, custom kitchen, state-of-the-art appliances, balconies. Dip in the heated pool (seasonal) or the hot tub, sauna, dine alfresco from the BBQ and watch the stars. Guests can enjoy morning coffee on the private deck or evening cocoa in front of the wood-burning fireplace or the fire pit, outside, overlooking a private pond.

4.98 out of 5 average rating, 177 reviews
Top guest favourite
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, 332 reviews
Superhost
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.

4.89 out of 5 average rating, 225 reviews
Guest favourite
A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.
Home in Putnam Valley

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, 144 reviews
Guest favourite
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 Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

4.99 out of 5 average rating, 149 reviews
Guest favourite
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!

4.89 out of 5 average rating, 279 reviews
Top guest favourite
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

Wake up next to a burbling creek in this immaculately clean full-floor apartment in the best possible location in Beacon. Just steps to Main Street, Roundhouse, Hudson Valley Brewery, and so much hiking. Perfect for a car-free escape (you can walk everywhere). Easy access to Metro-North train, Dia: Beacon. Walk to Mt Beacon hiking. Also near: Storm King, Breakneck Ridge, West Point. Permit# 2O26-OO27.STR (Please click the "Show More" button below for more info!)

4.92 out of 5 average rating, 465 reviews
Top guest favourite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman

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, 463 reviews
Top guest favourite
The restored a-frame stone cottage is nestled among trees, featuring a wooden deck and stone steps leading to the entrance. A propane grill is positioned on the deck, with a tranquil wooded backdrop showcasing the colors of nature.
Cottage in Pawling

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.

4.99 out of 5 average rating, 190 reviews

Popular amenities for waterfront rentals in Philipstown

KitchenWifiPoolFree parking on premisesAir conditioning

Waterfront apartment rentals

Top guest favourite
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

4.96 out of 5 average rating, 560 reviews
Superhost
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

4.78 out of 5 average rating, 724 reviews
Top guest favourite
Flat in Beacon

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

4.92 out of 5 average rating, 334 reviews
Top guest favourite
A modern studio features a spacious bed draped in white bedding with blue accents, alongside a cozy seating area with a dark sofa. Floor-to-ceiling glass windows provide stunning views of the river and open onto a private terrace, enhancing the serene ambiance.
Flat in Ulster Park

Escape to a Sleek, Serene Studio on the Riverbank

4.99 out of 5 average rating, 462 reviews
Guest favourite
The exterior of the cabin is illuminated by soft lighting, highlighting the double doors and windows. The building features a sloped roof and is surrounded by lush greenery, creating a serene environment in the evening. A simple bench is positioned on the grassy area in front.
Flat in Millbrook

The Bennett Cabin

4.86 out of 5 average rating, 121 reviews
Top guest favourite
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, 235 reviews
Guest favourite
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

4.95 out of 5 average rating, 320 reviews
Top guest favourite
A spacious living area features a futon decorated with patterned cushions and a striking red pool table. A light fixture with multiple bulbs hangs overhead, while a wall-mounted TV is visible in the background. Large pocket doors separate the living space from the bedroom.
Flat in Kingston

Lovely 1 bedroom apt. with free parking in Rondout

4.98 out of 5 average rating, 238 reviews

Waterfront house rentals

Top guest favourite
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!

4.94 out of 5 average rating, 375 reviews
Guest favourite
An outdoor area is visible through a large window, featuring a vintage clawfoot bathtub and a wooden stool. A hammock is suspended nearby. Lush greenery surrounds the space, creating a serene atmosphere.
Home in Spring Glen

Creekside cottage on 65 acres of land

4.94 out of 5 average rating, 249 reviews
Guest favourite
The lakeside property features a well-manicured lawn leading to the water's edge, complemented by a dock and a single kayak. Lounge chairs are arranged near a shaded gazebo, with a stone pathway guiding guests towards the house, which is framed by lush greenery.
Home in Greenwood Lake

Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC

4.97 out of 5 average rating, 117 reviews
Top guest favourite
A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.
Home in Rhinebeck

Slate Cabin - Stylish Country Escape x Rhinebeck

4.98 out of 5 average rating, 132 reviews
Guest favourite
Home in Danbury

Lakeview Estate - Chef's Kitchen - NYC Getaway

4.94 out of 5 average rating, 142 reviews
Guest favourite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

4.88 out of 5 average rating, 222 reviews
Top guest favourite
Home in Wappingers Falls

Tranquil Tree-House on the beautiful Hudson River

4.94 out of 5 average rating, 302 reviews
Guest favourite
An outdoor seating area is featured with two ornate egg chairs and a spacious sofa. The furniture is complemented by colorful cushions, and a geometric patterned rug is placed underneath. A stone fireplace is visible in the background, surrounded by trees.
Home in New Fairfield

Hilltop Retreat- Lakefront with Dock

4.95 out of 5 average rating, 105 reviews

Waterfront apartment rentals

Top guest favourite
A cozy living area features a warm fireplace, surrounded by modern furnishings. Large windows allow natural light to fill the space, and decorative curtains frame the view. A dining table is positioned nearby, complemented by upholstered chairs and tasteful decor.
Apartment in Vernon Township

Luxury Romantic Hideaway

4.96 out of 5 average rating, 81 reviews
Guest favourite
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 Township

Walk to Mountain Creek Hot Tub 09-23M

4.81 out of 5 average rating, 100 reviews
Top guest favourite
The exterior of a multi-unit condominium building showcases a blend of wood and stone elements. Green trim accents the balconies and entries, while a clear blue sky provides a bright backdrop. Well-maintained landscaping features grassy areas and plants near the entrance.
Apartment in Vernon Township

Little Getaway at the Black Creek Sanctuary

4.99 out of 5 average rating, 97 reviews
Guest favourite
A wooden dock extends into a calm lake, featuring two black Adirondack chairs positioned for relaxing views. Flags stand on either side of the dock, with greenery and reeds framing the scene. The sky is partly cloudy, and lush trees are visible in the background.
Apartment in Montague

Tranquility on the Lake!

5.0 out of 5 average rating, 16 reviewsA 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

Private room in Matamoras

Spacious Private Room with 2 Queen Beds &Bathroom

New place to stay

When is the best time to visit Philipstown?

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Avg. price€186€185€180€197€256€278€244€297€233€262€227€174
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C

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