
House vacation rentals in Philipstown
Find and book unique houses on Airbnb
Quick stats about house rentals in Philipstown

Total vacation rentals
Explore 210 vacation rentals in Philipstown

Nightly prices starting at
Philipstown vacation rentals start at G$10,462 GYD per night before taxes and fees

Verified guest reviews
Over 9,570 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wi-Fi availability
210 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!
Top-rated house rentals in Philipstown
Guests agree: these houses are highly rated for location, cleanliness, and more.

Accord River House
Welcome to our house in the woods! 12 acres surrounded by trees and above a series of waterfalls along the Stony Kill, which runs all the way from Minnewaska State Park through our property and into downtown Accord. You can sit in a hammock outside, soak in our hot tub while listening to the river, or chill out inside with some tunes or the TV projector. Budding entomologists will enjoy the endless procession of bugs, ants, spiders, ticks, and other creepy-crawlies that is part of River House.
LocationValueWalkability

Modern 3BD West Point USMA House w/ HotTub!
Our beautiful 3 bed, 2 bath contemporary home sits just 0.4 miles from West Point Military Academy. The house is equipped with super fast internet, work stations in each bedroom, cozy nectar mattresses, a 4-person jacuzzi, and of course, an incredible back yard patio with a BBQ, fire pit and outdoor dining area. Our kitchen is stocked for coffee lovers with 3 different types of machines ( Nespresso, Keurig, and Miele). There are also Samsung Smart TV's in each bedroom along with Sonos speakers!
ValueFamilyGetting around

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
ValueLocationTV

Boulder Tree House
Boulder Tree House 🌲🌲🌲 SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee 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 an exciting, romantic, unique experience but can accommodate a 3rd person.
LocationFamilyQuiet

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.
ValueLocationRiver

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.
FamilyValueBathroom

River & Mtn Views - Jacuzzi - near Metro North
Panoramic Hudson River & Storm King Mountain views, just a 5-minute walk from train station, 3 minutes to Dia Beacon. Walk to Main Street. (Or ride one of the house bikes!) Watch the sun set over the Hudson River from the Jacuzzi (or the outdoor shower) at this prime location. My kitchen is fully equipped with more than just basics. Also, Weber grill out on the deck is hooked to gas line. Includes Linens, Towels & Toiletries. House also has Iron, Ironing Board and Hair Dryer.
ValueLocationHot tub

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.
ValueLocationHeating

Hudson Valley Hygge House~ comfort in the country!
Experience the cozy charm of hygge at the farmhouse by a tranquil pond in Rosendale. Nestled in the Hudson Valley, just minutes from Kingston, Stone Ridge, and High Falls—and only 90 miles from NYC—this retreat offers pure serenity. Located on a quiet country road, enjoy the sounds of birdsong, evening frog lullabies, and a gas fireplace for a cozy winter escape. Set on over 3 acres, nature abounds here. Come and enjoy all the Hudson Valley has to offer!
ValueLocationLayout

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.
FamilyLocationComfort

The Foundry House by the Hudson River
The Foundry House is an ivy covered historic brick home, built in 1800. It was used as workers quarters for West Point Foundry and its lumberyard during the Civil War until 1911. It has been beautifully restored into a cozy and comfortable home. It’s located on a quiet street a block away from Main Street, half a block away from the Hudson River and the Bandstand, and a minute walk to Cold Spring Metro North Hudson Line Train Station.
ValueLocationQuiet

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring
Escape the hustle and bustle of city life and unwind in the peaceful surroundings of this luxurious retreat. With a sauna, steam room, and pool, our home offers something for everyone. Whether you are enjoying the spa like amenities or cozying up by the wood-burning stove you will have an incredible time staying with us. Don't wait, book your perfect getaway now and recharge your mind, body, and soul at our idyllic oasis!
FamilyValueTV
Popular amenities for Philipstown house rentals
House rentals with a pool

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
LocationFamilyDecor

Farmhouse w/ Pool, Sauna & Hot Tub near Storm King
FamilyValueCondition

Entire Home, Private Indoor Pool
LocationFamilyCheck-in

Luxe modern A Frame, Hot tub and new heated pool
LocationFamilyNearby

Peace & Privacy - High Falls (hot tub & salt pool)
ValueLocationAccuracy

midcentury mod hot tub*walk out trail R2R/Mohonk
FamilyLocationBeach

4Br Mountain Brook House on 130 acres w/ trails
LocationValueOutdoor spaces
Woodstock Historic Artist Estate - The Pond House
LocationFamilyHiking
Weekly house rentals

Lower Hudson Valley Idyllic Retreat
FamilyValueHospitality

Modern Upstate Gem Surrounded by Trees and Hot Tub
ValueLocationPets

The Pudding Pad Lake House
LocationValueWalkability

Mt hikes, city strolls river walks
ValueFamilyHospitality

Crystal Wave LakeHouse
ValueLocationBackyard

NEW! Stylish Home in the Heart of Beacon
ValueLocationRiver

Cozy House 3 Blocks From West Pt
ValueLocationQuiet

Top-Rated West Point 3 Bed 2 Bath Walk to Thayer
ValueLocationComfort
Private house rentals

Panoramic Lakeviews & Lush Garden | Beach Access
ValueFamilyOutdoor spaces

Architect's Hudson Valley Home in the Woods
ValueFamilyCheckout

Tranquil Tree-House on the beautiful Hudson River
LocationValueSolo travel

Peaceful & Spacious Retreat
LocationFamilyCondition

Luxury Townhouse Near West Point
ValueLocationLayout

Arkadia House Mid-century retreat with pool & view
FamilyValueGetting around

Mountainside Home (Beacon/Cold Spring)
LocationFamilyWalkability

Home in Cold Spring- Farm Stay!
FamilyLocationAmenities
When is the best time to visit Philipstown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$68,001 GYD | G$73,232 GYD | G$68,628 GYD | G$73,232 GYD | G$86,832 GYD | G$81,182 GYD | G$81,601 GYD | G$83,065 GYD | G$75,533 GYD | G$79,509 GYD | G$80,136 GYD | G$73,232 GYD |
| 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 |
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- Rentals with beach access Philipstown
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- Family-friendly rentals Philipstown
- Pet-friendly rentals Philipstown
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- Rentals with a hot tub Philipstown
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- Times Square
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