
House holiday 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.
Woodstock Historic Artist Estate - The Pond House
Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Your West Point Academy Home Away from Home
Make yourselves at home in this lovely, privately-owned residence as you attend West Point Academy events and tour scenic Hudson Valley. Build in 1900 and renovated in 2019, this house combines historic charm (original wood floors) with modern conveniences. The home's location is a twelve-minute drive to West Point's Washington Gate and within walking distance to the restaurants and shops of Cornwall. Enjoy 4th of July fireworks and weekly summer concerts with ease relaxing on the front porch!

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

Cozy 3 bedroom house on quiet private road
3 bedroom house overlooking creek on a quiet, private road. Minutes from Metro North Railroad, Hudson River, historic Cold Spring Village, Highlands Country Club golf course, Beacon, downtown Peekskill, Bear Mountain State Park, Boscobel House & Gardens, Fahenstock St Park and West Point Military Academy. Restaurants, farmer’s markets, hiking trails. We are dog friendly but there is an additional fee of $80 per stay. I live close by so I’m available for help or assistance during your stay.

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.

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.

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.

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.

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.

Charming Home in Peekskill NY
Enjoy this stylish home located less than a 10 minute drive from many walking/biking trails and tons of restaurants and local entertainment. It is also a 2 minute drive from the NY Presbyterian Hudson Valley Hospital perfect for Traveling Nurses and other short-term healthcare professionals. The neighborhood is quiet and situated at the end of a cul-de-sac, so there is no through traffic, suitable for walking your dog.
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

Design Farmhouse w/ Pool + Firepit | Hudson Valley

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

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Cozy & Spacious Country Home - All Seasons

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis
Weekly house rentals

Cottage in the village of Cold Spring

Cabin with a View

Andes Cottage

Bedford Paradise Getaway | Hot Tub | Town Center

The Waterfall House

Arkadia House Mid-century retreat with pool & view

Home in Cold Spring- Farm Stay!

Modern, sun-filled farmhouse retreat
Private house rentals

Tranquil Hudson Valley Retreat with Cedar Hot Tub

Spring Villa- Fully Renovated Eco Friendly Cottage

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

Charming *Country House* 3BR Fireplace Hiking

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

Charming Home in Cold Spring, NY

Cloud 9

Modern Luxe Lakefront Cabin
When is the best time to visit Philipstown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $483 AUD | $433 AUD | $426 AUD | $469 AUD | $581 AUD | $558 AUD | $554 AUD | $564 AUD | $513 AUD | $540 AUD | $544 AUD | $497 AUD |
| 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 holiday rentals
Explore 200 holiday rentals in Philipstown

Nightly prices starting at
Philipstown holiday rentals start at $71 AUD per night before taxes and fees

Verified guest reviews
Over 9,010 verified reviews to help you choose

Family-friendly holiday rentals
170 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 70 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wi-Fi availability
200 of Philipstown holiday 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!
Destinations to explore
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- Rentals with lake access Philipstown
- Rentals with a fire pit Philipstown
- Rentals with beach access Philipstown
- Rentals with a washing machine and dryer Philipstown
- Rentals with a kayak Philipstown
- Family-friendly rentals Philipstown
- Pet-friendly rentals Philipstown
- Fitness-friendly rentals Philipstown
- Apartment rentals Philipstown
- Rentals with an EV charger Philipstown
- Rentals with a fireplace Philipstown
- Rentals with a patio Philipstown
- Rentals with a hot tub Philipstown
- Rentals with breakfast Philipstown
- Rentals with pools Philipstown
- Rentals with outdoor seating Philipstown
- Waterfront rentals Philipstown
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