House vacation rentals in Philipstown

Find and book unique houses on Airbnb

Quick stats about house rentals in Philipstown

  • Total vacation rentals

    Explore 210 vacation rentals in Philipstown

  • Nightly prices starting at

    Philipstown vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 9,570 verified reviews to help you choose

  • Family-friendly vacation rentals

    170 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wi-Fi availability

    210 of Philipstown vacation rentals include wi-fi 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 house rentals in Philipstown

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

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Top guest favorite
A contemporary two-story home is presented, featuring a combination of wood and gray siding. Stone steps lead to an inviting entrance, while surrounding greenery provides a natural backdrop. Large windows allow for ample natural light, enhancing the exterior's modern design.
Home in Highland Falls
4.99 out of 5 average rating, 112 reviews

Modern 3BD West Point USMA House w/ HotTub!

Our beautiful 3 bed, 2 bath contemporary home sits just 0.4 miles from West Point Military Academy. The house is equipped with super fast internet, work stations in each bedroom, cozy nectar mattresses, a 4-person jacuzzi, and of course, an incredible back yard patio with a BBQ, fire pit and outdoor dining area. Our kitchen is stocked for coffee lovers with 3 different types of machines ( Nespresso, Keurig, and Miele). There are also Samsung Smart TV's in each bedroom along with Sonos speakers!

Superhost
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
Home in Newburgh
4.81 out of 5 average rating, 134 reviews

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

Top guest favorite
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
4.99 out of 5 average rating, 189 reviews

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

Superhost
A charming cottage is framed by trees, with a welcoming yellow door nestled among the greenery. A stone pathway leads to the entrance, bordered by well-maintained grass. Natural light filters through the surrounding foliage, enhancing the peaceful ambiance of the setting.
Home in Cold Spring
4.93 out of 5 average rating, 168 reviews

Peaceful Yellow Door Cottage

Yellow Door Cottage is a quiet family getaway nestled in the woods, but close to the historic Village of Cold Spring. Large backyard, ideal for afternoon lunch on the deck or an evening around the fire. Located on a lovely country road, great for walking and biking. 3 comfy bedrooms with linens supplied. Wi-Fi, TVs, washer/dryer, close to amazing hikes and the beautiful Hudson River! Rent alone or pair with my cottage next door: Cheerful Private 3 Bedroom Cottage in Cold Spring on Airbnb.

Superhost
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
4.94 out of 5 average rating, 137 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.

Superhost
A charming home nestled among trees features a spacious front porch adorned with planter boxes. Lush greenery and colorful flower beds surround the property, and a large boulder adds a natural element to the landscape.
Home in Cold Spring
5.0 out of 5 average rating, 100 reviews

Home in Cold Spring- Farm Stay!

Escape to our charming home nestled on five acres of farmland. This stay offers both seclusion and convenience, providing an ideal retreat for families, friends, or anyone seeking a peaceful countryside experience. Outdoor Space: -Walkable property featuring goats, chickens, horses, and donkeys -Large front porch featuring stunning mountain views and sunsets -Nearby hiking trails Location: -Five-minute drive to the quaint village of Cold Spring -Many shops, restaurants, and river views

Superhost
The exterior of a cottage is presented, featuring a gravel driveway and a single garage. Surrounding trees showcase autumn foliage while a small wooden deck is visible above the garage. The mountains can be seen in the distance beneath a partly cloudy sky.
Home in Philipstown
4.86 out of 5 average rating, 140 reviews

Bear Mtn Haus near hiking trails

Welcome to our cozy and thoroughly cleaned Garrison cottage steps to Anthony's Nose hiking trail, minutes from the Bear Mountain bridge, just 60min from NYC, 15 min to Cold Spring shops and restaurants, 8 min drive from the Garrison train stop. Set on the mountainside, we have lovely partial views of the Hudson river. Short drive to Woodbury Commons Premium Outlet mall and close to Storm King, and Beacon. Our house is suitable for 6 people, but can accommodate 8 at an extra charge.

Top guest favorite
A spacious living area is centered around a stone fireplace, adorned with wood beams. Natural light filters through large glass doors, offering views of the greenery outside. Comfortable couches are positioned invitingly, creating a relaxing atmosphere for guests.
Home in Cold Spring
4.95 out of 5 average rating, 177 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Superhost
An outdoor space features a circular fire pit surrounded by four wooden chairs. The grass is trimmed, and a deck is visible in the background, providing a cozy area for gatherings. Trees are scattered around the yard, contributing to the natural setting.
Home in Highland Falls
4.93 out of 5 average rating, 177 reviews

Cozy House 3 Blocks From West Pt

Welcome to this thoughtfully remodeled Historic 1890s home, just steps away from West Point's Thayer Gate. The house is conveniently situated right by Thayer Gate (3 blocks) where there are shuttles to all events and destinations. Steps away (1 block) from the restaurants on Main street and the West Point visiting center and Museum (3 blocks). 10 Mins to Bear Mountain State Park 15 Mins to Storm King Art Center 20 Mins to Woodbury Commons

Superhost
A sunlit seating area features light-colored, oversized chairs and a round coffee table. Large sliding glass doors open to a view of the forest, enhancing the connection to nature. A minimalistic pendant light hangs elegantly above, while a decorative plant adds a touch of greenery.
Home in Cold Spring
4.95 out of 5 average rating, 368 reviews

Hilltop Hideaway Forest Villa on 13 acres!

Our artistic, spacious , comfortable home is set on 13 (fairytale-esque) private, forest acres. We are minutes away from hiking trails, swimming lakes, and the Hudson River where you can kayak. The house is located on 13 acres of land just minutes away from the vibrant shopping of downtown Cold Spring, NY. It is surrounded by lakes and hiking trails, including the Appalachian Trail. We are minutes away from the Cold Spring train station.

Guest favorite
A comfortable living area features a cozy couch with assorted cushions, positioned near a stone fireplace. Natural light filters through a window, illuminating wooden beams and eclectic decor on the wall shelves. A coffee table and a few chairs complete the inviting space.
Home in Cold Spring
4.9 out of 5 average rating, 224 reviews

The Foundry House by the Hudson River

The Foundry House is an ivy covered historic brick home, built in 1800. It was used as workers quarters for West Point Foundry and its lumberyard during the Civil War until 1911. It has been beautifully restored into a cozy and comfortable home. It’s located on a quiet street a block away from Main Street, half a block away from the Hudson River and the Bandstand, and a minute walk to Cold Spring Metro North Hudson Line Train Station.

Guest favorite
An outdoor pool area features a stone patio surrounded by vibrant flowers and greenery. Lounge chairs are arranged neatly beside the pool, and a wooden cabana is visible with a stone fireplace, creating a relaxing atmosphere for guests.
Home in Philipstown
4.82 out of 5 average rating, 106 reviews

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

Escape the hustle and bustle of city life and unwind in the peaceful surroundings of this luxurious retreat. With a sauna, steam room, and pool, our home offers something for everyone. Whether you are enjoying the spa like amenities or cozying up by the wood-burning stove you will have an incredible time staying with us. Don't wait, book your perfect getaway now and recharge your mind, body, and soul at our idyllic oasis!

Popular amenities for Philipstown house rentals

When is the best time to visit Philipstown?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 1,194ﺩ.ﺇ 1,285ﺩ.ﺇ 1,205ﺩ.ﺇ 1,285ﺩ.ﺇ 1,524ﺩ.ﺇ 1,425ﺩ.ﺇ 1,432ﺩ.ﺇ 1,458ﺩ.ﺇ 1,326ﺩ.ﺇ 1,396ﺩ.ﺇ 1,407ﺩ.ﺇ 1,285
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