Title: Philipstown Vacation Home Rentals from CA $355: Search Top Private Vacation Homes for Rent | Expedia.ca [Philipstown Travel Guide](https://expedia.ca/Philipstown.dx553248635975876159)[Hotels in Philipstown](https://expedia.ca/Philipstown-Hotels.d553248635975876159.Travel-Guide-Hotels)[Vacation Rentals in Philipstown](https://expedia.ca/Philipstown-Vacation-Rentals.d553248635975876159.Travel-Guide-VacationRentals)[Philipstown Car Rentals](https://expedia.ca/Car-Rentals-In-Philipstown.d553248635975876159.Car-Rental-Guide)[Philipstown Vacation Packages](https://expedia.ca/Philipstown.d553248635975876159.Destination-Travel-Guides) ![Such a peaceful place. #Patterns](https://images.trvl-media.com/place/553248635975876159/1df8a79c-69ee-4a03-9af0-025459f90b75.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by louann ohora # Philipstown Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635975876159&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635975876159&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635975876159&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635975876159&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Philipstown vacation homes ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/424d87c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/9832ea44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e73b5292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/92f8429f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Highland Falls [](https://www.expedia.ca/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information) 10/10 Exceptional (5) "A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria L. CA $157 CA $506 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/bdac6c18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/4388309b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/d8805194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/fd769a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Holmes [](https://www.expedia.ca/Holmes-Hotels-Country-Outside-The-City-3-Bedrooms-2-Full-Bathrooms.h109381685.Hotel-Information) 9.6/10 Exceptional (4) "Great house! We had a fantastic weekend!! Thank you so much " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) pamela w. CA $240 CA $746 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Holmes-Hotels-Country-Outside-The-City-3-Bedrooms-2-Full-Bathrooms.h109381685.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116740000/116735700/116735677/3f1be5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116740000/116735700/116735677/da7ad181.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices, computer monitors](https://images.trvl-media.com/lodging/117000000/116740000/116735700/116735677/b5059923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116740000/116735700/116735677/f762b52e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in New Paltz [](https://www.expedia.ca/New-Paltz-Hotels-Quaint-Cozy-Cottage-Close-To-Town-Pet-Friendly.h116735677.Hotel-Information) 10/10 Exceptional (3) "Lovely home in a beautiful area of New York state. Would stay here again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason W. CA $199 CA $744 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/New-Paltz-Hotels-Quaint-Cozy-Cottage-Close-To-Town-Pet-Friendly.h116735677.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/38809636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/8bc06f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/cfa82cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/07a03d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Carmel Hamlet [](https://www.expedia.ca/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information) 9.8/10 Exceptional (12) "We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah P. CA $229 CA $489 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/7ad8e5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/82ecc5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/b762fce3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/cf889632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Highland Falls [](https://www.expedia.ca/Highland-Falls-Hotels-Sleek-Escape-Modern-3-BR-4-Min-From-West-Point.h110986250.Hotel-Information) 10/10 Exceptional (2) "Looked like this property was recently renovated. Very clean and nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellie M. CA $209 CA $598 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Highland-Falls-Hotels-Sleek-Escape-Modern-3-BR-4-Min-From-West-Point.h110986250.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/6a09d677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/719e347a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/e5c54a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/3207c5e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Highland Falls [](https://www.expedia.ca/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information) 10/10 Exceptional (7) "Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Molly s. CA $197 CA $406 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/be15b260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/8cbcd139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/0c2d8c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/116022ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Highland Falls [](https://www.expedia.ca/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information) 9.0/10 Wonderful (4) "Clean home, conveniently located to West Point. Very comfortable beds. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle B. CA $197 CA $381 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107760000/107753600/107753545/03e4ca4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/108000000/107760000/107753600/107753545/18d8bd06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, stereo](https://images.trvl-media.com/lodging/108000000/107760000/107753600/107753545/ba65c6e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/108000000/107760000/107753600/107753545/ce68fd9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Warwick [](https://www.expedia.ca/Warwick-Hotels-5-Min-To-Downtown-Warwick.h107753545.Hotel-Information) 10/10 Exceptional (5) "Had a lovely weekend in the little red barn. And the little market next door has the best breakfast egg and bacon sandwich." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michelle d. CA $187 CA $503 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Warwick-Hotels-5-Min-To-Downtown-Warwick.h107753545.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/d2d9d4e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/5a612bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/d7a0c7a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/537494b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Goshen [](https://www.expedia.ca/Goshen-Hotels-Renovated-House-WHot-Tub.h77280503.Hotel-Information) 10/10 Exceptional (58) "Clean and comfortable accommodations, very close to Legoland and Castle Fun Center! The kids loved the room with bunk beds, and it had a big selection of children's books and some toys, which was a nice bonus!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer K. CA $341 CA $656 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Goshen-Hotels-Renovated-House-WHot-Tub.h77280503.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/161ac482.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/0dcdc2c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/cbf53a35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/e2171280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Hopewell Junction [](https://www.expedia.ca/Hopewell-Junction-Hotels-Cozy-1845-Chapel-Escape-Near-Appalachian-Trail-And-Fahnestock-Park.h88181115.Hotel-Information) 9.0/10 Wonderful (10) "We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Esther P. CA $209 CA $355 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Hopewell-Junction-Hotels-Cozy-1845-Chapel-Escape-Near-Appalachian-Trail-And-Fahnestock-Park.h88181115.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120390000/120384900/120384809/9c93ce23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120390000/120384900/120384809/f3de8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120390000/120384900/120384809/75b18da9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120390000/120384900/120384809/1c692607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Poughkeepsie [](https://www.expedia.ca/Poughkeepsie-Hotels-Stunning-5-Bedroom-House-With-AC-Heat-In-Charming-Poughkeepsie-NY.h120384809.Hotel-Information) 10/10 Exceptional (2) "Great host" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lindsey F. CA $241 CA $820 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Poughkeepsie-Hotels-Stunning-5-Bedroom-House-With-AC-Heat-In-Charming-Poughkeepsie-NY.h120384809.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/6b825ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/8fad8a9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/973f29b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/ae162913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Highland Falls [](https://www.expedia.ca/Highland-Falls-Hotels-3BR-West-Point-Retreat-3min-To-Back-Gate-King-Bed.h113522229.Hotel-Information) 7.6/10 Good (5) "We were supposed to check out at 10 AM, and everyone was still sleeping. But at 8 AM, very loud noises suddenly started. It felt like the whole roof was shaking and the house might fall down. We went outside and saw that workers were cleaning the roof. No one told us anything about this before. When we asked the cleaning manager, he said the landlord booked this cleaning two weeks ago, but we, the guests, were never informed. Also, our car was parked in the driveway, and the things falling from... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lixing CA $180 CA $623 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Highland-Falls-Hotels-3BR-West-Point-Retreat-3min-To-Back-Gate-King-Bed.h113522229.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/81000000/80870000/80863500/80863418/8c61ac04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis](https://images.trvl-media.com/lodging/81000000/80870000/80863500/80863418/db2022b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/81000000/80870000/80863500/80863418/1d988d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/81000000/80870000/80863500/80863418/25176bd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in wallkill [](https://www.expedia.ca/Wallkill-Hotels-NEW-PEACEFUL-WATERSCOMFORT.h80863418.Hotel-Information) 9.8/10 Exceptional (57) "Loved this property, clean, wonderful view of the river. Quite neighborhood. Great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mamie G. CA $245 CA $528 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Wallkill-Hotels-NEW-PEACEFUL-WATERSCOMFORT.h80863418.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/ef9b23f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/d5087de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/02671128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/b07ff9fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Fishkill [](https://www.expedia.ca/Fishkill-Hotels-Large-Relaxing-Family-Retreat-In-The-Hudson-Valley-With-Theatre-And-Gazebo.h111183358.Hotel-Information) 9.6/10 Exceptional (49) "Inside was very nice, outside could use some curb appeal. Enjoyed our stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen K. CA $341 CA $439 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Fishkill-Hotels-Large-Relaxing-Family-Retreat-In-The-Hudson-Valley-With-Theatre-And-Gazebo.h111183358.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83930000/83925200/83925171/05363ddd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83930000/83925200/83925171/f114158e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83930000/83925200/83925171/b51bb581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83930000/83925200/83925171/b806fd76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Mahopac [](https://www.expedia.ca/Mahopac-Hotels-Fun.h83925171.Hotel-Information) 10/10 Exceptional (12) "Super convenient location :)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean M. CA $465 CA $1,002 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Mahopac-Hotels-Fun.h83925171.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/122000000/121780000/121770200/121770157/59723039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/122000000/121780000/121770200/121770157/7abf4bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121780000/121770200/121770157/80029f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/122000000/121780000/121770200/121770157/86fd9c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Highland Falls [](https://www.expedia.ca/Highland-Falls-Hotels-Charming-3-Bedroom-House-With-AC.h121770157.Hotel-Information) CA $342 CA $439 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Highland-Falls-Hotels-Charming-3-Bedroom-House-With-AC.h121770157.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122970000/122963500/122963409/a7f39d48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/123000000/122970000/122963500/122963409/85a87f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/123000000/122970000/122963500/122963409/65551d2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122970000/122963500/122963409/64348083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Monroe [](https://www.expedia.ca/Monroe-Hotels-Lakeview-Escape-Scenic-Deck-Wi-Fi-Fire-Pit.h122963409.Hotel-Information) CA $225 CA $625 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Monroe-Hotels-Lakeview-Escape-Scenic-Deck-Wi-Fi-Fire-Pit.h122963409.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/b8d7ac80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/905a40e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/9015258a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/8dd5c447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Poughkeepsie [](https://www.expedia.ca/Poughkeepsie-Hotels-Cozy-Escape-Strong-Wi-Fi-Prime-Location.h110643700.Hotel-Information) 6.8/10 (5) "The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea C. CA $156 CA $480 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Poughkeepsie-Hotels-Cozy-Escape-Strong-Wi-Fi-Prime-Location.h110643700.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/124000000/123610000/123607600/123607576/854fb988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/124000000/123610000/123607600/123607576/05913227.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123610000/123607600/123607576/7e891032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123610000/123607600/123607576/1e208a42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Poughquag [](https://www.expedia.ca/Poughquag-Hotels-Tranquil-4-Bedroom-House-In-Welcoming-Poughquag-Neighborhood.h123607576.Hotel-Information) CA $220 CA $400 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Poughquag-Hotels-Tranquil-4-Bedroom-House-In-Welcoming-Poughquag-Neighborhood.h123607576.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/101000000/100670000/100661800/100661800/eb403423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100670000/100661800/100661800/c37104c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100670000/100661800/100661800/d7a17c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100670000/100661800/100661800/2c6360ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Greenwood Lake [](https://www.expedia.ca/Greenwood-Lake-Hotels-Waterfront-Modern-Home-WFast-Wifi-400m-From-DT.h100661800.Hotel-Information) 10/10 Exceptional (30) "We loved the house. It was a perfect and much needed short getaway for my husband and I. We brought our little dog Lenny and he loved it too! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chelsea D. CA $229 CA $633 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Greenwood-Lake-Hotels-Waterfront-Modern-Home-WFast-Wifi-400m-From-DT.h100661800.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-29&endDate=2025-12-30®ionId=553248635975876159&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPhilipstown-Private-Vacation-Homes.d553248635975876159-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPhilipstown-Private-Vacation-Homes.d553248635975876159-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Philipstown Hotel Reviews ![Hotel Nyack, a JdV by Hyatt Hotel](https://images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/a38df02c_y.jpg) ### Hotel Nyack, a JdV by Hyatt Hotel 10/10 Excellent "Accountability is the name of the game here. When I arrived to the hotel, the road was blocked off by firefighters for maybe an hour. I was tired from a long drive, so it was not how I needed to start the check-in process. I ended up parking on the street and walking to the hotel. A small fire in the laundry room was the cause of it all. They had to shut down the elevators, so they were asking everyone to take the stairs. I was tired and had bags, so I decided to go to the bar to wait until the elevators were working again. Accountability is the star here. The manager or someone who may have been a manager walked over to the bar and offered complimentary drinks. The next day I woke up to a notice on the door giving us 50% off the room rate and complimentary breakfast. The hotel is great esthetically, but the customer service takes it over the top. When I got up fornwork the next morning, the restaurant was closed. The person at the fromt desk apologized for that inconvenience and comped 100% of one of my nights there. I didn't fuss or complain about anything. They did all of that on their own and that was very impressive. I will definitely come back to this hotel for future work trips. The rooms look nice. The hotel is clean. No complaints at all. " [](https://expedia.ca/Nyack-Hotels-Hotel-Nyack.h11943081.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Great location, friendly staff. Highly recommend " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "Love it, everytime we come this is the place to stay" [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Hampton Inn Nanuet](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/af6569cb_y.jpg) ### Hampton Inn Nanuet 10/10 Excellent "The room was spotless and shiny and the king sided bed was comfortable " [](https://expedia.ca/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) ![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/w3839h2556x0y3-9a7a26d9_y.jpg) ### DoubleTree by Hilton Hotel Nanuet 10/10 Excellent "Clean, attractive hotel and courteous staff. Note the restaurant is only open for breakfast and dinner " [](https://expedia.ca/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![Holiday Inn Express & Suites Hawthorne Elmsford North by IHG](https://images.trvl-media.com/lodging/1000000/10000/2700/2692/789126d5_y.jpg) ### Holiday Inn Express & Suites Hawthorne Elmsford North by IHG 10/10 Excellent "Very nice stay! Quiet area, clean room and amazing staff! Will definitely stay again if back in the area" [](https://expedia.ca/White-Plains-Hotels-Comfort-Inn-Suites.h2692.Hotel-Information) ![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/a9ba8283_y.jpg) ### Sonesta Simply Suites Nanuet 10/10 Excellent "Clean" [](https://expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) ![Windrose On Hudson](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/f251141f_y.jpg) ### Windrose On Hudson 10/10 Excellent "Beautiful campus" [](https://expedia.ca/Ossining-Hotels-Crotonville-Hotel.h112806652.Hotel-Information) ![Crowne Plaza Suffern - Mahwah by IHG](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/e31233cf_y.jpg) ### Crowne Plaza Suffern - Mahwah by IHG 10/10 Excellent "Clean nice" [](https://expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) ## Find out more about Philipstown ## Philipstown Vacation Homes information | Number of reviews | 263 | | ----------------- | ------------------ | | Accommodation | 318 Vacation Homes | | Lowest Price | CA $355 | | Highest Price | CA $1,002 | ## Explore a world of travel with Expedia - 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