Philipstown Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Philipstown vacation rentals

Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.4 out of 10, Exceptional, (31 reviews)
"Great host! Cute tiny house with everything we needed. Location great as well. "
United States
Lisa R.
$170 nightly
The price is $201
Feb 23 - Feb 24
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 2

Hidden Lakefront Gem on a Gated Countryside Escape

Hidden Lakefront Gem on a Gated Countryside Escape
2.0 star property
Monroe
$303 nightly
The price is $343
Feb 23 - Feb 24
Total with taxes and fees
Hidden Lakefront Gem on a Gated Countryside Escape

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, (13 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
$328 nightly
The price is $355
Feb 24 - Feb 25
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$172 nightly
The price is $187
Feb 23 - Feb 24
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!

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, (32 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
$238 nightly
The price is $281
Feb 23 - Feb 24
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1

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
9.4 out of 10, Exceptional, (60 reviews)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
$282 nightly
The price is $282
Feb 23 - Feb 24
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
$367 nightly
The price is $420
Feb 23 - Feb 24
Total with taxes and fees
Contemporary Cozy Cottage

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 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
$257 nightly
The price is $279
Feb 23 - Feb 24
Total with taxes and fees
Charming 1-bedroom apartment in Carmel with WiFi, AC

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)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
$283 nightly
The price is $295
Feb 23 - Feb 24
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (67 reviews)
"Clean, simple, and comfortable with clear host directions on arrival, checkin & checkout."
United States
Lou F.
$268 nightly
The price is $317
Feb 23 - Feb 24
Total with taxes and fees
Cozy country efficiency in the Hudson Valley

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 reviews)
"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.
$273 nightly
The price is $312
Feb 23 - Feb 24
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Boutique King Suite at Orchard Lake Private Farm

Boutique King Suite at Orchard Lake Private Farm
2.0 star property
Monroe
$335 nightly
The price is $379
Feb 23 - Feb 24
Total with taxes and fees
Boutique King Suite at Orchard Lake Private Farm

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, (131 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
$269 nightly
The price is $304
Feb 26 - Feb 27
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
10.0 out of 10, Exceptional, (60 reviews)
"This cottage was perfect for our stay. We have family nearby and this was the perfect retreat after busy days. We will be booking again. The space is clean and welcoming the land is beautiful! "
United States
Heather A.
$493 nightly
The price is $514
Feb 23 - Feb 24
Total with taxes and fees
Country House w/Hot Tub, Deck, Grill & Fire Pit

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, (16 reviews)
"Great Unit."
United States
Rudy R.
$250 nightly
The price is $253
Feb 24 - Feb 25
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

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 reviews)
"The breakfast was lovely!"
United States
Tara
$256 nightly
The price is $290
Feb 23 - Feb 24
Total with taxes and fees
Villa Verde B&B, bsm, Greenwood Lake NY

Rustic Lakefront Studio with Deck & Workspace

Rustic Lakefront Studio with Deck & Workspace
Monroe
$255 nightly
The price is $259
Feb 23 - Feb 24
Total with taxes and fees
Rustic Lakefront Studio with Deck & Workspace

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, (5 reviews)
$333 nightly
The price is $393
Feb 23 - Feb 24
Total with taxes and fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

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, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
$356 nightly
The price is $376
Mar 24 - Mar 25
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Beacon
10.0 out of 10, Exceptional, (53 reviews)
"We havld a good time. The room was comfortable and perfectly located!"
United States
Brandy C.
$217 nightly
The price is $250
Mar 1 - Mar 2
Total with taxes and fees
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Philipstown Hotel Reviews

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 $201 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 Stonecrop Gardens, 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 23 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 Putnam History Museum and Manitoga The Russel Wright Design Center. 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.