Philipstown Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Philipstown holiday rentals

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, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$855
HK$1,616 total
includes taxes & fees
12 May - 13 May
Cozy 1-bedroom retreat minutes from West Point!
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 HK$1,120
HK$3,224 total
includes taxes & fees
11 May - 12 May
House on the Babbling Brook- Quiet 2BR + King Bed!
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 HK$901
HK$2,404 total
includes taxes & fees
11 May - 12 May
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
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 HK$862
HK$1,604 total
includes taxes & fees
11 May - 12 May
Hoppy Hill Farm House
Outdoor dining

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, (28 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is HK$1,010
HK$1,573 total
includes taxes & fees
10 May - 11 May
Cabin in the heart of the Hudson Valley, Cabin 4
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, (135 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is HK$1,473
HK$2,489 total
includes taxes & fees
11 May - 12 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is HK$837
HK$1,656 total
includes taxes & fees
10 May - 11 May
Historic Cabin with Pool & Fire Pit
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 HK$1,586
HK$3,086 total
includes taxes & fees
10 May - 11 May
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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 HK$1,057
HK$2,156 total
includes taxes & fees
9 May - 10 May
Charming 1-bedroom apartment in Carmel with WiFi, AC
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 HK$1,175
HK$2,322 total
includes taxes & fees
11 May - 12 May
Cozy country efficiency in the Hudson Valley
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 HK$1,501
HK$4,058 total
includes taxes & fees
11 May - 12 May
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
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 HK$1,324
HK$2,202 total
includes taxes & fees
10 May - 11 May
Cabin in the Heart of the Hudson Valley, Cabin 1
Iron/ironing board, WiFi, bed sheets

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is HK$1,128
HK$1,587 total
includes taxes & fees
11 May - 12 May
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Exterior detail

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, (56 reviews)
"Great location and quiet just like we like it. Unit was very charming."
Canada
Thomas
The price is HK$901
HK$1,948 total
includes taxes & fees
10 May - 11 May
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Interior

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, (81 reviews)
"great location and nice host"
United States
christopher s.
The price is HK$896
HK$1,811 total
includes taxes & fees
27 May - 28 May
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Exterior

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (11 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is HK$1,191
HK$2,003 total
includes taxes & fees
9 May - 10 May
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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 HK$1,163
HK$2,292 total
includes taxes & fees
14 May - 15 May
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Exterior detail

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (47 reviews)
"Great place to stay. Cozy, warm, and clean! The host was also a good communicator and everything went smoothly."
United States
Samantha Esmé W.
The price is HK$901
HK$1,885 total
includes taxes & fees
12 May - 13 May
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is HK$1,567
HK$2,542 total
includes taxes & fees
10 May - 11 May
Luxury House Near West Point
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 HK$1,057
HK$2,304 total
includes taxes & fees
1 Jun - 2 Jun
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

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

8/10 Good
"Good breakfast, clean room confortable beds"
Virginie 1-night trip
Posted less than an hour ago
Baymont by Wyndham White Plains - Elmsford

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 holiday rentals in Philipstown?

Yes, there are holiday rentals in Philipstown close to Garrison Art Center, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Philipstown has to offer?

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This holiday home rental outside of Philipstown is located in the mountains, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Philipstown?

Choose from 26 Expedia holiday rentals in Philipstown for a memorable holiday.

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 Graymoor - The Holy Mountain and Clarence Fahnestock State Park.

What’s a holiday rental in Philipstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Philipstown. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for families.