A river with hills in the background.

Philipstown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Philipstown vacation rentals

A hallway with a wooden door, a black table with a sign, and large green plants.

1. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Clean and convenient near West Point golf course"
United States
mario b.
The price is ￥20,023
￥68,756 total
includes taxes & fees
Nov 1 - Nov 2
3BR Near West Point | Coffee Bar | Sleeps 6
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

2. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.6 out of 10, Exceptional, (21 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
The price is ￥19,474
￥64,490 total
includes taxes & fees
Nov 1 - Nov 2
Local Artist Inspired | Walk to WestPoint + King Bed
A historic building with a central tower labeled 'West Point Museum,' featuring a traditional architectural style with multiple windows and a stone facade.

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is ￥13,874
￥41,211 total
includes taxes & fees
Nov 2 - Nov 3
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

4. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is ￥34,246
￥58,116 total
includes taxes & fees
Dec 1 - Dec 2
Fabulous 3bdrm Home w/parking!
A house with a view of a bridge and mountains.

5. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (149 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥31,197
￥49,693 total
includes taxes & fees
Nov 2 - Nov 3
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

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

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
The price is ￥22,072
￥72,175 total
includes taxes & fees
Nov 1 - Nov 2
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A blue house with a white porch, a welcome sign, and a mailbox.

7. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is ￥20,180
￥71,267 total
includes taxes & fees
Nov 3 - Nov 4
3BR West Point Retreat-3min to Back Gate+ King Bed
A living room with a fireplace, a painting, shelves with decorative items, and a television.

8. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (52 reviews)
"Beautiful little apartment, walking to shops and easy parking"
United States
Martha Z.
The price is ￥31,197
￥54,185 total
includes taxes & fees
Nov 4 - Nov 5
Grant - A Tranquil One Bedroom Steps from River
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

9. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is ￥31,599
￥51,348 total
includes taxes & fees
Nov 17 - Nov 18
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A room with a wooden floor, a white door with a number, and a window with blinds.

10. Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is ￥32,426
￥57,456 total
includes taxes & fees
Dec 1 - Dec 2
Lovely 3BR Home with parking-Walk to WP Gate!
A modern kitchen with wooden cabinets, a stainless steel stove, a microwave, and a toaster. There are stools and a small island with a plant.

11. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
The price is ￥33,584
￥53,818 total
includes taxes & fees
Dec 1 - Dec 2
Walk to WP Gate + Free Parking!
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

12. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (42 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
The price is ￥35,451
￥63,073 total
includes taxes & fees
Nov 1 - Nov 2
Contemporary Cozy Cottage
A brick building with a sign reading 'Lobby' in front.

13. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveler
The price is ￥12,399
￥14,337 total
includes taxes & fees
Nov 23 - Nov 24
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A deck with Adirondack chairs, a fire pit, and a grill.

14. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Cornwall
10.0 out of 10, Exceptional, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is ￥35,158
￥67,604 total
includes taxes & fees
Nov 11 - Nov 12
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

15. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveler
The price is ￥12,399
￥14,025 total
includes taxes & fees
Nov 21 - Nov 22
1 King Bed | Non-Smoking, Kitchen, Shower
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

16. Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (35 reviews)
"Very comfortable house and great location."
United States
Betty B.
The price is ￥48,402
￥107,086 total
includes taxes & fees
Nov 22 - Nov 23
Bright Cornwall-On-Hudson Vacation Rental!
An outdoor patio area with a covered seating area, a pool, and potted plants.

17. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (81 reviews)
"The property was as advertised and met our needs for our trip."
United States
Sara
The price is ￥43,108
￥51,667 total
includes taxes & fees
Nov 4 - Nov 5
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Living area

18. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ￥17,536
￥32,030 total
includes taxes & fees
Dec 1 - Dec 2
Cozy 1-bedroom retreat minutes from West Point!
A modern kitchen with grey cabinets, stainless steel appliances, a granite countertop, and a wooden floor.

19. 2-bedroom apartment in excellent Newburgh with AC and charm

2-bedroom apartment in excellent Newburgh with AC and charm
Newburgh
10.0 out of 10, Exceptional, (3 reviews)
"We have stayed here once before overnight while in the area for an event. It is close to where we needed to be and a great value for the price"
United States
Nick L.
The price is ￥29,779
￥36,362 total
includes taxes & fees
Nov 11 - Nov 12
2-bedroom apartment in excellent Newburgh with AC and charm
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

The Thayer Hotel at West Point

The Thayer Hotel at West Point

10/10 Excellent
"amazing"
David 1-night trip
Posted 8 hours ago
The Thayer Hotel at West Point

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 vacation rentals in Philipstown?

Yes, we offer vacation rentals in Philipstown near Manitoga The Russel Wright Design Center, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Philipstown?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This vacation home rental outside of Philipstown is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Philipstown?

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

What can I see and do in Philipstown?

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

What’s a vacation rental in Philipstown like?

Vacation rentals are private properties you can stay in for short or long periods in Philipstown. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family gatherings.