A river with hills in the background.

Philipstown Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Philipstown vacation rentals

Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

Jellystone Park Gardiner

Jellystone Park Gardiner
3.0 star property
Gardiner
Jellystone Park Gardiner
Property grounds

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, (140 reviews)
"We had a great stay!!"
United States
Jasmine
$280 nightly
The price is $331
Jul 20 - Jul 21
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cottage (2 Bedrooms) | Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
$457 nightly
The price is $517
Aug 6 - Aug 7
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (9 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
$463 nightly
The price is $517
Jul 20 - Jul 21
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
Property grounds

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
wallkill
9.8 out of 10, Exceptional, (59 reviews)
"This is a wonderful property. Very clean and well maintained. It was centrally located to everything we needed. The outdoor area is amazing! We really enjoyed sitting by the river and having coffee in the morning"
United States
Nate B.
$365 nightly
The price is $409
Jul 20 - Jul 21
Total with taxes and fees
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
TV

Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (24 reviews)
"Would definitely stay here again! It was a great experience!"
United States
Jodi P.
$342 nightly
The price is $381
Jul 23 - Jul 24
Total with taxes and fees
Walk to WP Gate + Free Parking!
Terrace/patio

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 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
$236 nightly
The price is $279
Jul 19 - Jul 20
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
Internet, bed sheets

Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
$170 nightly
The price is $184
Jul 19 - Jul 20
Total with taxes and fees
Welcome to Sweet Abby Rose!
Paper towels

Amazing 3-bedroom house with AC in adorable Highland

Amazing 3-bedroom house with AC in adorable Highland
Highland
$512 nightly
The price is $573
Jul 29 - Jul 30
Total with taxes and fees
Amazing 3-bedroom house with AC in adorable Highland
Smart TV

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$285 nightly
The price is $297
Jul 19 - Jul 20
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
1 bedroom, WiFi (free)

2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (20 reviews)
"Schöne Zimmer, Internet war kostenpflichtig, funktionierte aber nicht. Das Personal war jedoch nett."
Germany
Anonymous traveler
$100 nightly
The price is $113
Aug 17 - Aug 18
Total with taxes and fees
2 Queen Beds | Non-Smoking, Kitchen
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.
Carmel Hamlet
9.8 out of 10, Exceptional, (17 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
$367 nightly
The price is $397
Jul 22 - Jul 23
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Terrace/patio

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, (10 reviews)
"Good stay, awesome place"
United States
Scott G.
$378 nightly
The price is $400
Jul 21 - Jul 22
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
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!
Wallkill
10.0 out of 10, Exceptional, (87 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
$205 nightly
The price is $230
Aug 10 - Aug 11
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Interior

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
$301 nightly
The price is $326
Jul 19 - Jul 20
Total with taxes and fees
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Interior

Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
$259 nightly
The price is $263
Jul 19 - Jul 20
Total with taxes and fees
Harriman Outdoor Center - Mountain Laurel Cabin
Smart TV

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (46 reviews)
"This apartment was perfect for what we needed! Beautifully renovated, comfortable bed, and very close to Beacon! "
United States
Abby W.
$260 nightly
The price is $294
Aug 3 - Aug 4
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
House (4 Bedrooms) | Interior

Family Home Close to Warwick, 5 Mi to Lake!

Family Home Close to Warwick, 5 Mi to Lake!
3.0 star property
Monroe
$645 nightly
The price is $730
Aug 2 - Aug 3
Total with taxes and fees
Family Home Close to Warwick, 5 Mi to Lake!
Coffee/tea maker, fridge, microwave, oven

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.
$399 nightly
The price is $446
Jul 29 - Jul 30
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Private kitchen

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, (2 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.
$216 nightly
The price is $244
Jul 26 - Jul 27
Total with taxes and fees
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

Spark by Hilton Fishkill

Spark by Hilton Fishkill

8/10 Good
"Bed was very comfortable and room was well air conditioned. Room and bathroom were very small and “no frills”. Just the bare minimum. Continental breakfast was a small selection. Good for an inexpensive stay."
Lorraine 2-night trip
Posted 8 hours ago
Spark by Hilton Fishkill

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 $98 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?

Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town: Visitors like this Philipstown vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a hot tub.

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 Garrison Art Center 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.