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.

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Guest favourite
A spacious outdoor area is accessed from the cabin's deck, featuring a hot tub surrounded by stone paving. Comfortable seating arrangements include two blue lounge chairs and a small bistro table with wrought iron chairs. The natural setting includes a backdrop of trees and rocky terrain.
Apartment in Philipstown
4.9 out of 5 average rating, 269 reviews

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.

Guest favourite
Apartment in Cold Spring
4.9 out of 5 average rating, 330 reviews

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

Guest favourite
The cottage is nestled among tall trees, with natural rock formations in the foreground. The structure features a combination of brown siding and large windows, providing a blend of indoor comfort and outdoor scenery. A grassy area extends around the property.
Cottage in Cold Spring
4.93 out of 5 average rating, 177 reviews

Cheerful Private 3 Bedroom Cottage in Cold Spring

Relax with friends & family at this peaceful forrest cottage, just 7-minutes outside of The Historic Village of Cold Spring on a beautiful, quiet country road. Much bigger on the inside than it looks, this place has what you need: fresh linens, full kitchen, wifi, streaming tvs and plenty of great books to read. There is a trampoline in the backyard & patio lights for Spring/Summer/Fall nights dining outside. Rent alone or pair with my cottage next door: Peaceful Yellow Door Cottage on Airbnb.

Top Guest favourite
A spacious living area features a gray sectional couch adorned with decorative pillows. A circular white coffee table sits in front, complemented by a dark media unit holding various entertainment items. Natural light enters through the windows, illuminating the walls decorated with framed artwork.
Home in Putnam Valley
4.99 out of 5 average rating, 170 reviews

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

Top Guest favourite
Guesthouse in Beacon
4.95 out of 5 average rating, 417 reviews

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.

Guest favourite
A striking wooden wall showcases a large bank of windows offering panoramic views of Lake Oscawana and surrounding foliage. The vaulted ceiling emphasizes the spaciousness of the room, inviting natural light to fill the space.
Cottage in Putnam Valley
4.88 out of 5 average rating, 311 reviews

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.

Top Guest favourite
A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.
Home in Staatsburg
4.99 out of 5 average rating, 127 reviews

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.

Guest favourite
A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.
Home in Putnam Valley
4.96 out of 5 average rating, 119 reviews

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.

Guest favourite
A charming red cabin is nestled among the tall trees, surrounded by a landscape coated in autumn leaves. The exterior showcases a simple design with multiple windows, and a serene atmosphere is created by the natural surroundings and the peaceful yard.
Cabin in Putnam Valley
4.94 out of 5 average rating, 162 reviews

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!

Top Guest favourite
A cozy sitting room features exposed wooden beams and a brick fireplace. Two comfortable leather chairs are arranged around a wooden coffee table. Natural light enters through multiple windows adorned with sheer curtains, illuminating the space, which is enhanced by decorative touches like artwork and plants.
Guesthouse in Philipstown
4.99 out of 5 average rating, 146 reviews

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.

Top Guest favourite
A private yard features two blue Adirondack chairs surrounded by lush greenery and various plants. The area is accented by decorative elements hanging from a tree, creating a serene and inviting outdoor space.
Condo in Beacon
4.99 out of 5 average rating, 651 reviews

Rustic Spa Retreat

10 minute walk to Main Street (many restaurants, cafes, galleries, etc) 10 minute walk to Mt Beacon TrailHead. (It's not a hotel and not on Main Street: it's in a residential neighborhood) Cozy, small space set up for a couple (or solo traveler) looking for a relaxing short escape from "The Real World". A couple days here really feels likes so much longer (especially if you take a steam and a jacuzzi)!

Guest favourite
A light-colored cottage exterior features large glass doors, surrounded by trees displaying vibrant autumn colors. A stone pathway leads to the entrance, with a lantern and potted plants adding a welcoming touch. A picnic area is visible in the yard, set against the beautiful natural backdrop.
Cottage in Philipstown
4.97 out of 5 average rating, 219 reviews

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 holiday rentals

When is the best time to visit Philipstown?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$448 NZD$462 NZD$409 NZD$406 NZD$448 NZD$443 NZD$460 NZD$460 NZD$440 NZD$475 NZD$479 NZD$441 NZD
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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 cottage rentals in Philipstown?

    Experience the best of Philipstown with our cottage rentals, starting at about $200 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 apartment rentals in Philipstown have wifi?

    Absolutely! We offer over 50 apartment rentals with wifi in Philipstown. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Philipstown have free parking?

    Absolutely! We offer over 200 house 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 wifi, over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with air conditioning, 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 $68 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!

Destinations to explore

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  2. United States
  3. New York
  4. Putnam County
  5. Philipstown