
Holiday houses in Philipstown
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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 - Mountain Views - 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.

Cozy 3 bedroom house on quiet private road
3 bedroom house overlooking creek on a quiet, private road. Minutes from Hudson Valley Shakespeare, 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.

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.

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.

Mountain View Retreat
15 Minutes drive from Cold Spring & Beacon. 1 hour, 15 min by train or car from NYC. High-speed internet (wifi cell), cable, central AC, fireplace, large deck, mountain views, portable fire pit, gas grill and a 8 person hot tub. Featured in TIME OUT, "Best Airbnb Hudson Valley Rentals" Price change after 8 guests. Add guest number when booking, you can adjust it after booking. Specify beds you will need.

Viridian House
This space offers a romantic getaway for couples looking to enjoy the scenic Hudson Valley. If you are traveling solo, this cozy space is a private oasis for relaxation and leisure. Centered in the heart of Marlboro wine country, this space is right in the middle of several local wineries, breweries, farms, restaurants, and is just a short drive to the Shawangunk Mountains.
Popular amenities for Philipstown holiday rentals
Other great holiday rentals in Philipstown

Private Lake House 1 Hour to NYC & Near Westpoint

The Waterfall Casita: A-frame with 30ft Waterfall

Bear Mtn Haus near hiking trails

Andes Cottage

Cozy 1-bedroom retreat minutes from West Point!

Arkadia House Mid-century retreat with pool & view

Home in Cold Spring- Farm Stay!

Modern, sun-filled farmhouse retreat
When is the best time to visit Philipstown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $389 NZD | $388 NZD | $358 NZD | $412 NZD | $455 NZD | $450 NZD | $467 NZD | $467 NZD | $446 NZD | $483 NZD | $486 NZD | $448 NZD |
| 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 230 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Philipstown?
Experience the best of Philipstown with our apartment rentals, starting at about $70 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 apartment rentals in Philipstown have a kitchen?
Absolutely! We offer over 40 apartment rentals with a kitchen in Philipstown. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Philipstown have wifi?
Absolutely! We offer over 40 apartment 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 Cottage Rentals in Philipstown?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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 $69 NZD 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!
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- Rentals with a patio Philipstown
- Pet-friendly rentals Philipstown
- Rentals with lake access Philipstown
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- Rentals with a fire pit Philipstown
- Rentals with a fireplace Philipstown
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