
Vacation rentals in Philipstown
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Top-rated vacation rentals in Philipstown
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

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.

Cliff Top at Turtle Rock
Cliff Top retreat with a one hundred mile view of the Shawangunk's and the Catskill Mountains, surrounded by thousands of acres of ancient forest. Conveniently located in the Hudson Valley Wine and Orchard country. Twenty minutes from Beacon and New Paltz. Furnished with mid-century and 18th century period furniture and art work, yet with all the modern conveniences. Uber and Lift an easy five minutes away. The ancient forest contains many Stone Age rock shelters and calendar sites.

The Treecastle at the Roundhouse Homestead
The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

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.

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.

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.
Popular amenities for Philipstown vacation rentals
Other great vacation rentals in Philipstown

Tranquil Hudson Valley Retreat with Cedar Hot Tub

Modern 3BD West Point USMA House w/ HotTub!

Cabin with a View

Peaceful Forest Cabin

Accord River House

Arkadia House Mid-century retreat with pool & view

Charming *Country House* 3BR Fireplace Hiking

Home in Cold Spring- Farm Stay!
When is the best time to visit Philipstown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ970 | ﺩ.ﺇ999 | ﺩ.ﺇ885 | ﺩ.ﺇ878 | ﺩ.ﺇ970 | ﺩ.ﺇ959 | ﺩ.ﺇ995 | ﺩ.ﺇ995 | ﺩ.ﺇ951 | ﺩ.ﺇ1,028 | ﺩ.ﺇ1,036 | ﺩ.ﺇ955 |
| 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 private suite rentals in Philipstown have air conditioning?
Absolutely! We offer over 10 private suite rentals with air conditioning in Philipstown. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Philipstown have a kitchen?
Absolutely! We offer over 190 house rentals with a kitchen in Philipstown. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Philipstown have wifi?
Absolutely! We offer over 210 house rentals with wifi in Philipstown. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Philipstown have free parking?
Absolutely! We offer over 40 apartment rentals with free parking in Philipstown. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Philipstown?
Enhance your stay in our House Rentals with the most popular amenities: over 210 homes with wifi, over 200 homes with free parking, over 190 homes with a kitchen, over 200 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Philipstown

Total vacation rentals
Explore 320 vacation rentals in Philipstown

Nightly prices starting at
Philipstown vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 120 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wi-Fi availability
310 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 outdoor seating Philipstown
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- Family-friendly rentals Philipstown
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