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Philipstown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Philipstown vacation rentals

A historic building with a central tower labeled 'West Point Museum,' featuring a traditional architectural style with multiple windows and a stone facade.

1. 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 CA $170
CA $423 total
includes taxes & fees
Nov 9 - Nov 10
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
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 CA $182
CA $593 total
includes taxes & fees
Nov 11 - Nov 12
Local Artist Inspired | Walk to WestPoint + King Bed
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

3. 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 CA $194
CA $352 total
includes taxes & fees
Nov 8 - Nov 9
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

4. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is CA $201
CA $377 total
includes taxes & fees
Nov 9 - Nov 10
Perfect 2BR with Free Parking! Walk to West Point!
Living area

5. 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 CA $156
CA $282 total
includes taxes & fees
Dec 8 - Dec 9
Cozy 1-bedroom retreat minutes from West Point!
A dining area with a table, chairs, a vase with flowers, a hanging light fixture, and wall decorations.

6. Mountain-View 2BR Steps from Thayer Gate

Mountain-View 2BR Steps from Thayer Gate
Highland Falls
The price is CA $181
CA $352 total
includes taxes & fees
Nov 8 - Nov 9
Mountain-View 2BR Steps from Thayer Gate
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 CA $196
CA $663 total
includes taxes & fees
Nov 10 - Nov 11
3BR West Point Retreat-3min to Back Gate+ King Bed
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

8. 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 CA $218
CA $413 total
includes taxes & fees
Nov 8 - Nov 9
Fabulous 3bdrm Home w/parking!
A room with a wooden floor, a white door with a number, and a window with blinds.

9. 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 CA $242
CA $457 total
includes taxes & fees
Nov 9 - Nov 10
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.

10. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean, modern, functional, comfortable. Great stay"
United States
Jerell T.
The price is CA $218
CA $383 total
includes taxes & fees
Nov 8 - Nov 9
Walk to WP Gate + Free Parking!
A hallway with a wooden door, a black table with a sign, and large green plants.

11. 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 CA $181
CA $591 total
includes taxes & fees
Nov 9 - Nov 10
3BR Near West Point | Coffee Bar | Sleeps 6
A brick building with a sign reading 'Lobby' in front.

12. 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 traveller
The price is CA $111
CA $128 total
includes taxes & fees
Nov 25 - Nov 26
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

13. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is CA $258
CA $478 total
includes taxes & fees
Nov 9 - Nov 10
Hudson Valley/West Point Retreat w/ parking!
A living room with a fireplace, a painting, shelves with decorative items, and a television.

14. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (53 reviews)
"Beautiful little apartment, walking to shops and easy parking"
United States
Martha Z.
The price is CA $278
CA $504 total
includes taxes & fees
Nov 8 - Nov 9
Grant - A Tranquil One Bedroom Steps from River
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 traveller
The price is CA $100
CA $113 total
includes taxes & fees
Nov 22 - Nov 23
1 King Bed | Non-Smoking, Kitchen, Shower
A deck with Adirondack chairs, a fire pit, and a grill.

16. 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 CA $318
CA $614 total
includes taxes & fees
Nov 10 - Nov 11
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A deck with wicker furniture and a view of a lake and mountains.

17. Private River View Deck · Walk Downtown

Private River View Deck · Walk Downtown
Newburgh
10.0 out of 10, Exceptional, (1 review)
The price is CA $217
CA $606 total
includes taxes & fees
Nov 30 - Dec 1
Private River View Deck · Walk Downtown
A modern kitchen with grey cabinets, stainless steel appliances, a granite countertop, and a wooden floor.

18. 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 CA $265
CA $327 total
includes taxes & fees
Nov 23 - Nov 24
2-bedroom apartment in excellent Newburgh with AC and charm
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

19. 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 CA $315
CA $561 total
includes taxes & fees
Nov 11 - Nov 12
Contemporary Cozy Cottage
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

20. Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (31 reviews)
"Everything was just as it was in our past stays. The place was clean, neat and organized very well. Communication with the host was very easy and almost immediate reply."
United States
Albert
The price is CA $209
CA $311 total
includes taxes & fees
Nov 8 - Nov 9
Cabin in the heart of the Hudson Valley, Cabin 4
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

A spacious lobby with a high ceiling, a reception desk, a seating area with blue sofas and armchairs, and a visible Pepsi refrigerator.
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
Fishkill

10/10 Excellent

Bon rapport qualité-prix
Canada
Steeve
Reviewed August 2, 2026
Comfort Suites Fishkill near Interstate 84

Find out more about Philipstown

Everything you need to know about Philipstown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Philipstown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Philipstown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Philipstown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Philipstown. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Philipstown vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Philipstown vacation rentals we have selected for you start as low as CA $99 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Philipstown rentals

At Expedia, we put the best Philipstown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Philipstown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Philipstown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Philipstown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.