
Holiday houses in Philipstown
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Quick stats about holiday rentals in Philipstown

Total holiday rentals
Explore 320 holiday rentals in Philipstown

Nightly prices starting at
Philipstown holiday rentals start at $58 AUD per night before taxes and fees

Verified guest reviews
Over 21,440 verified reviews to help you choose

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

Pet-friendly accommodation
Find 120 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wi-Fi availability
310 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!
Top-rated holiday rentals in Philipstown
Guests agree: these stays are highly rated for location, cleanliness and more.

Ranch in the Woods | A Peaceful Designer Retreat
Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Foxglove Farm
Peace and tranquility await you at the end of this private road surrounded by forest. My home is a log cabin with a private apartment on the lower level, which includes a patio as well as use of other outdoor spaces. There is a fire pit just past your patio and a short path will put you on the Appalachian Trail. As an herbalist and ethnobotanist, plants are my love and my livelihood. They are an integral part of my life and my home. I welcome you to stroll through the many gardens and paths.

HOT Sauna/COLD Plunge- Mountains-Hiking-NYC Trains
Your SPA - Cedar Barrel HOT SAUNA - Outdoor Cozy updated 1814 Cold Spring Village Classic-NATIONAL Historic Register Close to West Point & Beacon Guest Jack's comments "This apartment gave me the feel that I had my own place in a beautiful river town" Mountain Views - Sunny (12+ Windows) 3 Bedroom Modern Garden Apartment (850+SF) Cozy for 1 to 6 #1 Coffees & Teas Walk to Waterfalls, Hiking Trails, River Beaches, NYC trains Restaurants & cafes Outdoor living space in Garden - birds

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 Mountainside Suite - Minutes from Beacon
The Equestrian Suite at Lambs Hill is a private estate with panoramic views overlooking the Hudson River & downtown Beacon. This beautifully-designed luxury suite sits atop a barn home to Icelandic horses & miniature donkeys, & features an outdoor hot tub, red light therapy, gourmet kitchen, & wrap-around decks. 1 mile to Beacon's Main St, 2 miles to Metro North train station & DIA: Beacon. We can host a max of 2 guests & have some dangerous features for kids so guests should be adults only.

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.

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.

Sweet, stylish cabin in the woods- hiking & more!
Only an hour north of NYC, but a world away! Adorable cabin in the woods offering stylish updated decor and beautiful natural surroundings. Brand new and completely renovated interior, but all the classic charm of the country. Trade in skyscrapers for tall trees in this sweet country escape that is near Fahnestock Park (surrounded by great hiking, skiing, etc) and 15m from the village of Cold Spring. Fully set up w/ wifi, Netflix & more! Quiet, considerate guests only please!

Historic 1 bedroom home in Cold Spring, NY
This lovingly restored home, built in 1826,is located within the hamlet of Nelsonville within walking distance of the village of Cold Spring. This home has its own entrance and private courtyard and is attached to the owners main residence. Space is curated with antiques and is intended for a couple. This is cozy any time of the year. This home is near trailheads of spectacular hikes in the Hudson Highlands and at the base of Bull Hill.

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.

Modern Country Cottage by Bear Mountain
Wake up feeling rejuvenated in a lofted bedroom beneath a wood-paneled ceiling with skylight windows. Descend a spiral staircase into a warm kitchenette for a cup of coffee, then have a seat in an airy living room beside a brass-plated decorative fireplace. Enjoy a picnic or grill on the front lawn and explore the 4 acres of most authentic Hudson Valley landscape.

Charming Village Base. Walk to Restaurants & Shops
Charming 1 BR apartment in the heart of Cold Spring. Centrally located in walking distance to restaurants and shops as well as hiking trails. About 15 min walk from Cold Spring train station. Ideally located in a Town Home in the village of Cold Spring with a private entrance.
Popular amenities for Philipstown holiday rentals
Other great holiday rentals in Philipstown

The Little Cottage in the Woods

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Viridian House

Arkadia House Mid-century retreat with pool & view

Accord River House

Green Country Home ~ Hot Tub ~ Privacy

Peekskill Carriage House Downtown Studio
When is the best time to visit Philipstown?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $382 AUD | $393 AUD | $349 AUD | $346 AUD | $382 AUD | $377 AUD | $392 AUD | $392 AUD | $375 AUD | $405 AUD | $408 AUD | $376 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 |
Frequently Asked Questions
Are there family-friendly vacation rentals in Philipstown?
Philipstown has more than 220 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Philipstown?
Experience the best of Philipstown with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Philipstown?
Four-legged friends are welcome in Philipstown. Choose from more than 120 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Philipstown?
Yes! Work meets play with ease at over 210 vacation rentals in Philipstown featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Philipstown vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Philipstown, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in Philipstown have air conditioning?
Absolutely! We offer over 40 apartment rentals with air conditioning in Philipstown. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Philipstown have a kitchen?
Absolutely! We offer over 10 cottage rentals with a kitchen in Philipstown. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Philipstown have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Philipstown. Enjoy a tailored experience with all the comforts you desire.
Do private suite rentals in Philipstown have free parking?
Absolutely! We offer over 10 private suite rentals with free parking in Philipstown. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Philipstown?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with air conditioning, over 40 homes with a kitchen, over 50 homes with wifi, over 40 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
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- Fitness-friendly rentals Philipstown
- Rentals with a fireplace Philipstown
- House rentals Philipstown
- Rentals with beach access Philipstown
- Rentals with a washing machine and dryer Philipstown
- Rentals with lake access Philipstown
- Rentals with breakfast Philipstown
- Rentals with pools Philipstown
- Rentals with a kayak Philipstown
- Family-friendly rentals Philipstown
- Pet-friendly rentals Philipstown
- Apartment rentals Philipstown
- Rentals with an EV charger Philipstown
- Rentals with a hot tub Philipstown
- Rentals with outdoor seating Philipstown
- Rentals with a patio Philipstown
- Waterfront rentals Philipstown
- Rentals with a fire pit Philipstown
- Times Square
- MetLife Stadium
- Madison Square Garden
- Central Park Zoo
- New York City Center
- Yankee Stadium
- Columbia University
- Mountain Creek Resort
- American Dream
- United Nations Headquarters
- Rockefeller Center
- Empire State Building
- Bryant Park
- Citi Field
- Grand Central Terminal
- Bear Mountain State Park
- Radio City Music Hall
- Minnewaska State Park Preserve
- Astoria Park
- Fairfield Beach
- Thunder Ridge Ski Area
- New York University
- The Metropolitan Museum of Art
- Brooklyn Bridge





