Philipstown Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Philipstown vacation rentals

Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
The price is ￥17,461
￥32,324 total
includes taxes & fees
May 18 - May 19
Hoppy Hill Farm House
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, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥11,112
￥50,603 total
includes taxes & fees
May 17 - May 18
House on the Babbling Brook- Quiet 2BR + King Bed!
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (68 reviews)
"Such a cute place to stay"
United States
Melissa
The price is ￥23,811
￥47,254 total
includes taxes & fees
May 27 - May 28
Cozy country efficiency in the Hudson Valley
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, (13 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥32,145
￥62,534 total
includes taxes & fees
May 17 - May 18
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Property grounds

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
10.0 out of 10, Exceptional, (2 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
The price is ￥23,811
￥49,030 total
includes taxes & fees
May 20 - May 21
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Exterior detail

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is ￥30,080
￥81,331 total
includes taxes & fees
May 18 - May 19
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
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, (137 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is ￥31,431
￥52,504 total
includes taxes & fees
May 18 - May 19
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior

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, (35 reviews)
"Great host! Cute tiny house with everything we needed. Location great as well. "
United States
Lisa R.
The price is ￥20,477
￥31,690 total
includes taxes & fees
May 18 - May 19
Cabin in the heart of the Hudson Valley, Cabin 2
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (2 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 ￥19,501
￥35,919 total
includes taxes & fees
May 27 - May 28
Cozy 1-bedroom retreat minutes from West Point!
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is ￥31,748
￥51,525 total
includes taxes & fees
Jun 3 - Jun 4
Luxury House Near West Point
Private kitchen

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
The price is ￥21,430
￥43,696 total
includes taxes & fees
May 17 - May 18
Charming 1-bedroom apartment in Carmel with WiFi, AC
Fridge, oven, stovetop, coffee/tea maker

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, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
The price is ￥11,906
￥41,386 total
includes taxes & fees
May 17 - May 18
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
1 bedroom, iron/ironing board, free WiFi, bed sheets

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)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is ￥26,827
￥44,252 total
includes taxes & fees
May 17 - May 18
Cabin in the Heart of the Hudson Valley, Cabin 1
Exterior detail

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (36 reviews)
"Stunning property!!"
United States
Samantha
The price is ￥43,654
￥76,394 total
includes taxes & fees
May 18 - May 19
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
House (3 Bedrooms) | Interior

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
The price is ￥38,803
￥98,469 total
includes taxes & fees
Jun 2 - Jun 3
Updated Home w/ Patio Half Mile to West Point
Exterior

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is ￥31,589
￥37,839 total
includes taxes & fees
May 18 - May 19
Luxury home near West Point
Outdoor dining

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, (65 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is ￥39,288
￥51,670 total
includes taxes & fees
May 19 - May 20
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Interior

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (50 reviews)
"We loved our stay. The room was so comfortable and had everything we needed. We loved being abl to walk to so many great restaurants and bars. "
United States
Amanda W.
The price is ￥19,049
￥40,569 total
includes taxes & fees
May 20 - May 21
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
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.
The price is ￥23,573
￥46,443 total
includes taxes & fees
May 17 - May 18
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
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, (42 reviews)
"Great lil tranquil home. Had all the things you'd need with some bonus touches and Stan was very quick and easy to communicate with. "
United States
Jen G.
The price is ￥21,430
￥46,870 total
includes taxes & fees
May 18 - May 19
Grant - A Tranquil One Bedroom Steps from River
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
"Yes."
Karen 1-night trip
Posted 5 hours ago
Spark by Hilton Fishkill

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
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  • 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 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?

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This vacation home rental outside of Philipstown is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

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 Graymoor - The Holy Mountain and Clarence Fahnestock State Park.

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.