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Philipstown Holiday Rentals

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Check prices for these dates

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Philipstown holiday rentals

Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 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
Maria L.
The price is HK$840
HK$2,857 total
includes taxes & fees
12 Jan - 13 Jan 2026
House on the Babbling Brook- Quiet 2BR + King Bed!
Exterior detail
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
The price is HK$700
HK$2,069 total
includes taxes & fees
19 Jan - 20 Jan 2026
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Fridge, microwave, oven, stovetop
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (46)
"Great location, so clean and comfortable. "
United States
Barbara
The price is HK$894
HK$1,934 total
includes taxes & fees
7 Jan - 8 Jan 2026
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
3 bedrooms, iron/ironing board, travel cot, WiFi
"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
2.0 star property
Holmes
9.6 out of 10, Exceptional, (4)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is HK$1,463
HK$4,206 total
includes taxes & fees
5 Jan - 6 Jan 2026
"Country outside the city " 3 bedrooms 2 full bathrooms
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
3.0 star property
Carmel
10.0 out of 10, Exceptional, (3)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
United States
Varuna S.
The price is HK$997
HK$2,058 total
includes taxes & fees
30 Dec - 31 Dec
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Children’s area
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (12)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is HK$1,155
HK$2,275 total
includes taxes & fees
29 Dec - 30 Dec
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is HK$1,050
HK$2,166 total
includes taxes & fees
27 Dec - 28 Dec
Charming 1-bedroom apartment in Carmel with WiFi, AC
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is HK$988
HK$3,401 total
includes taxes & fees
14 Jan - 15 Jan 2026
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Interior
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Putnam Valley
9.8 out of 10, Exceptional, (23)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$2,246
HK$4,902 total
includes taxes & fees
27 Dec - 28 Dec
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
2 bedrooms, in-room safe, desk, iron/ironing board
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is HK$874
HK$2,147 total
includes taxes & fees
28 Dec - 29 Dec
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
Interior
Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
The price is HK$1,221
HK$2,252 total
includes taxes & fees
1 Jan - 2 Jan 2026
Villa Verde B&B, bsm, Greenwood Lake NY
Smart TV
Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (41)
"Wonderful place! Beautifully decorated, high ceilings, yard, and easy access to the river and cafes. Perfect getaway from the city. Will stay again!"
United States
Emily G.
The price is HK$840
HK$2,014 total
includes taxes & fees
30 Dec - 31 Dec
Grant - A Tranquil One Bedroom Steps from River
Outdoor dining
Hoppy Hill Farm House

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.6 out of 10, Exceptional, (4)
"The cabin was perfect. Had everything we needed and clear directions. "
United States
Jocelyn L.
The price is HK$778
HK$1,513 total
includes taxes & fees
13 Jan - 14 Jan 2026
Hoppy Hill Farm House
Property grounds
3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
7.6 out of 10, Good, (5)
"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "
United States
Waylon J.
3BR West Point Retreat-3min to Back Gate+ King Bed
Fridge, microwave, oven, stovetop
Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.2 out of 10, Wonderful, (9)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is HK$855
HK$3,116 total
includes taxes & fees
12 Jan - 13 Jan 2026
Local Artist Inspired | Walk to WestPoint + King Bed
Fridge, microwave, oven, stovetop
Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is HK$1,314
HK$2,168 total
includes taxes & fees
28 Dec - 29 Dec
Cabin in the heart of the Hudson Valley, Cabin 3
Property grounds
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (72)
"Everything was great nexactly as advertised. Terrific stargazing at night by the fire pit. Will definitely come back."
United States
David C.
The price is HK$896
HK$1,805 total
includes taxes & fees
29 Dec - 30 Dec
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is HK$1,295
HK$2,760 total
includes taxes & fees
5 Jan - 6 Jan 2026
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Property grounds
The Hideaway

The Hideaway

The Hideaway
Brewster
10.0 out of 10, Exceptional, (6)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
United States
Rick C.
The price is HK$1,205
HK$2,461 total
includes taxes & fees
28 Dec - 29 Dec
The Hideaway
Fridge, microwave, oven, stovetop
Lux APT Your home away from home.

Lux APT Your home away from home.

Lux APT Your home away from home.
Beacon
10.0 out of 10, Exceptional, (2)
"Very clean and great place to stay. "
United States
Charlene D.
The price is HK$1,104
HK$2,120 total
includes taxes & fees
7 Jan - 8 Jan 2026
Lux APT Your home away from home.
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.
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Top Philipstown Hotel Reviews

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

10/10 Excellent
"Very good "
Rafael 1-night trip
Posted 2 days ago
Baymont by Wyndham White Plains - Elmsford

Find out more about Philipstown

Search for holiday rentals in Philipstown on Expedia! You can easily find your home rentals, villas, holiday apartments in Philipstown using one of the methods below:

  • View our selection of featured holiday rentals in Philipstown
  • Use the map to find apartments and other holiday homes in the Philipstown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Philipstown while they last

Look no further and take a look at our great range of rental properties in Philipstown!

Frequently asked questions

Can I find holiday rentals in Philipstown?

Yes, there are holiday rentals in Philipstown close to Manitoga The Russel Wright Design Center, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Philipstown has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Philipstown offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and kitchenware, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Philipstown?

Choose from 26 Expedia holiday rentals in Philipstown for a memorable holiday.

What can I see and do in Philipstown?

Enjoy the outdoors at Hudson Highlands State Park and Hudson River, or simply take in cultural attractions like Boscobel House and Gardens and Manitoga The Russel Wright Design Center. Other places in town to visit include Clarence Fahnestock State Park and Graymoor - The Holy Mountain.

What’s a holiday rental in Philipstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Philipstown. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for families.