
House vacation rentals in Philipstown
Find and book unique houses on Airbnb
Top-rated house rentals in Philipstown
Guests agree: these houses are highly rated for location, cleanliness, and more.

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

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

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.

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.

Cozy Riverfront Victorian in the Hudson Valley
Wake up to stunning views of the Hudson River in this huge, immaculately clean, & beautifully designed historic home. Welcome to Sparrow House, our one-of-a-kind 1859 Gothic Victorian in the Hudson Valley. Only 80 minutes from NYC, 19 minutes away from the Beacon stop on the Hudson line/Metro-North, and 13 minutes from the Salisbury Mills/Cornwall Stop on the Port Jervis line/NJ Transit. The house is spacious, has exquisite light, and river and mountain views from nearly every room.

Spectacular Lake Views from Every Room & Garden
Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

The Little Red House
Located in a quiet neighborhood just off the Hudson River, yet only a 10 min drive from the bustling town of Beacon and within walking distance to the Newburgh action where you will find restaurants, coffee shops, galleries local shopping, and nightlife. With countless hiking spots, farms, breweries, and wineries, your stay in Hudson Valley will be memorable. The house was also a filming & staging location for the movie “Adults” starring Michael Cera

Peaceful & Spacious Retreat
Big and beautiful house fully renovated in 2020 sitting on half an acre of land in Mahopac. Open floor concept with high cathedral ceilings in living space. Kitchen fully stocked with everything you need to cook and bake. Oversized bedrooms and two bathrooms. Great for a weekend getaway (about 1hr drive from NYC). EV friendly - Tesla universal charger located at property to charger your Tesla or EV vehicle (integrated J1772 adapter) during your stay.

Lovely 3BR Home with parking-Walk to WP Gate!
Walk to West Point! Enjoy the Hudson Valley. Bring the whole family to this great place with lots of room for fun. Cozy up in our spacious living room while dinner is cooking in the fully equipped kitchen. The back deck is perfect for morning coffee, unwinding in the evening with a glass of wine or a family BBQ. You will find everything you need for work or play here in the heart of Highland Falls, New York. Looking forward to having you!

Creekside Home Near Cold Spring & West Point
Private 3BR home overlooking a peaceful creek on a quiet road. Minutes to Cold Spring, Beacon, Peekskill, the Hudson River, Metro-North, West Point, Bear Mountain, and top attractions like Boscobel and Hudson Valley Shakespeare. Close to hiking, golf, restaurants, and farmers markets. Dog-friendly ($80 per stay). Perfect for a relaxing Hudson Valley getaway.

View House
Magnificent views from this fully renovated octagonal, mid-century glass house on secluded hilltop site. Views of and close access to Storm King Art Center, Schunnemunk State Park, Black Rock Forest. 60 mi from Manhattan, Town of Cornwall, NY. Perfect getaway from the city.

The Waterfall House
Welcome! A two bedroom stone house overlooks two waterfalls, cascading into a private swimming hole. Huguenot style home , A great place to unplug ... and connect to nature. We’re located a short drive to many historic Hudson Valley attractions.
Popular amenities for Philipstown house rentals
House rentals with a pool

midcentury mod * POOL * walk out trail 2 mohonk

Entire Home (private pool), Event Friendly

4Br Mountain Brook House on 130 acres w/ trails

Scenic River View Escape | New Paltz

Design Scandi Retreat, Heated Pool, Dogs Welcome

Mountain Creek retreat PH w/pool & hot tub

GOOD VIBEZ HOUSE! Mini Golf+Pool+Hot Tub+Game Room

New Paltz dog friendly retreat w/ salt water pool
Weekly house rentals

Slate Cabin - Stylish Country Escape x Rhinebeck

Ultimate Walking Access to Thayer Gate USMA

The Barger Wixon House

Mountainside Home (Beacon/Cold Spring)

The Dugout • Cool Woodland Escape • 60 Min NYC

Arkadia House Mid-century retreat with pool & view

Wake up to this view all summer! Lakefront life!

Home in Cold Spring- Farm Stay!
Private house rentals

3.5 Acres of Relaxation, Pool, & Cozy Charm

Cottage in the village of Cold Spring

Cold Spring Hidden Gem: woods, walk to town, SAUNA

Gorgeous Water Views - Scenic Cold Spring Retreat

Charming *Country House* 3BR Fireplace Hiking

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

Charming Home in Cold Spring, NY

Mountain Top Retreat
When is the best time to visit Philipstown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,194 | ﺩ.ﺇ 1,285 | ﺩ.ﺇ 1,205 | ﺩ.ﺇ 1,212 | ﺩ.ﺇ 1,502 | ﺩ.ﺇ 1,443 | ﺩ.ﺇ 1,432 | ﺩ.ﺇ 1,458 | ﺩ.ﺇ 1,326 | ﺩ.ﺇ 1,396 | ﺩ.ﺇ 1,407 | ﺩ.ﺇ 1,285 |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
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 9,230 verified reviews to help you choose

Family-friendly vacation rentals
180 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 80 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!
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- Rentals with a fireplace Philipstown
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- Family-friendly rentals Philipstown
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- Rentals with an EV charger Philipstown
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- Rentals with a patio Philipstown
- Rentals with a hot tub Philipstown
- Waterfront rentals Philipstown
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- Rentals with pools Philipstown
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- Pet-friendly rentals Philipstown
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- Times Square
- Madison Square Garden
- New York City Center
- Central Park Zoo
- New York University
- Columbia University
- MetLife Stadium
- Mountain Creek Resort
- Yankee Stadium
- United Nations Headquarters
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- Empire State Building
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- American Dream
- USTA Billie Jean King National Tennis Center
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- Prudential Center
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