A river with hills in the background.

Philipstown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Philipstown vacation rentals

Living area

1. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (25 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
$405 nightly
The price is $453
Sep 29 - Sep 30
Total with taxes and fees
Walk to WP Gate + Free Parking!
Living area

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
9.0 out of 10, Wonderful, (4 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$234 nightly
The price is $260
Sep 29 - Sep 30
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
Living area

3. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (47 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
$254 nightly
The price is $287
Sep 7 - Sep 8
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
Exterior

4. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
10.0 out of 10, Exceptional, (17 reviews)
"Nice place to stay"
United States
Anonymous traveler
$82 nightly
The price is $94
Sep 30 - Oct 1
Total with taxes and fees
1 Queen Bed | Non-Smoking, Kitchen
Property grounds

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, (142 reviews)
"We had a great stay!!"
United States
Jasmine
$280 nightly
The price is $331
Sep 8 - Sep 9
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Interior

6. 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.
$417 nightly
The price is $479
Sep 29 - Sep 30
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
Room

7. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
8.6 out of 10, Excellent, (24 reviews)
"Worst hotel experience I have ever had. Grounds were unkept. No one was at the front desk when I first arrived. Waited 20 minutes for someone to arrive and had to leave for dinner. Came back to find out that they were overbooked."
United States
Glenn
$82 nightly
The price is $92
Sep 30 - Oct 1
Total with taxes and fees
2 Queen Beds | Non-Smoking, Kitchen
Terrace/patio

8. River Views & Deck | River Suite on Washington

River Views & Deck | River Suite on Washington
Newburgh
$345 nightly
The price is $406
Sep 7 - Sep 8
Total with taxes and fees
River Views & Deck | River Suite on Washington
Outdoor spa tub

9. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (13 reviews)
"Everything you could ask for!!"
United States
Elisabeth
$339 nightly
The price is $400
Sep 9 - Sep 10
Total with taxes and fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Exterior

10. Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.6 out of 10, Exceptional, (38 reviews)
"This was a great place to stay with our cats for a night on our way to Vermont."
United States
George J.
$191 nightly
The price is $226
Sep 7 - Sep 8
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 2
Exterior

11. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
$247 nightly
The price is $279
Sep 7 - Sep 8
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Private kitchen

12. 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.
$370 nightly
The price is $414
Sep 29 - Sep 30
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Exterior

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

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (19 reviews)
"Great place to stay,"
United States
Anonymous traveler
$82 nightly
The price is $94
Sep 30 - Oct 1
Total with taxes and fees
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Private kitchen

14. 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.
$214 nightly
The price is $242
Sep 10 - Sep 11
Total with taxes and fees
2-bedroom apartment in excellent Newburgh with AC and charm
Outdoor dining

15. 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, (74 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
$294 nightly
The price is $340
Sep 7 - Sep 8
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Lobby

16. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (18 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$74 nightly
The price is $83
Oct 1 - Oct 2
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
Room

17. Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (73 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
$300 nightly
The price is $354
Sep 9 - Sep 10
Total with taxes and fees
Cozy country efficiency in the Hudson Valley
Room

18. Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (36 reviews)
"Great place! Nicely decorated with attention to detail. My wife and I would stay again if we are back in the area."
United States
Tim G.
$230 nightly
The price is $272
Sep 8 - Sep 9
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
Exterior

19. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.4 out of 10, Exceptional, (20 reviews)
"great place tostay"
United States
Anonymous traveler
$90 nightly
The price is $104
Sep 30 - Oct 1
Total with taxes and fees
2 Full Beds | Non-Smoking, Kitchen
Exterior detail

20. 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.
$413 nightly
The price is $460
Sep 29 - Sep 30
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
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

8/10 Good
"The stay was fine."
James 1-night trip
Posted 1 hour ago
Baymont by Wyndham White Plains - Elmsford

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Philipstown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $94 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 Garrison Art 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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Philipstown?

Choose from 27 Expedia vacation rentals in Philipstown for a memorable vacation.

What can I see and do in Philipstown?

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

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.