Photo by Kiri Romero

Philipstown Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Philipstown

2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!

10.0 out of 10, Exceptional, (1)
"This condo is located very close to the Garrison train station. It has been designed so that you are never disturbed by the sound of the trains. Really soundproof! There is a beautiful view of West Point across the Hudson River from the balcony and other windows. The kitchen and 2 1/2 bathrooms are modern and well equipped. Matt, the host, has thought of everything when it comes to making his guests feel comfort and st home. The beds were extra comfy and both bedrooms were quite spacious....
2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (118)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
The price is NZ$509
includes taxes & fees
28 July - 29 July
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (299)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is NZ$982
includes taxes & fees
3 Aug - 4 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (16)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is NZ$1,002
includes taxes & fees
28 July - 29 July
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (26)
"Plenty of room for my family"
The price is NZ$587
includes taxes & fees
27 July - 28 July
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.6 out of 10, Exceptional, (8)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Magnificent Lake View

2.0 star property
Magnificent Lake View

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.2 out of 10, Wonderful, (35)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (84)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

6.0 out of 10, (1)
"Property was very clean and nicely decorated. There isn’t really a living room to hang out. Very difficult for 3 adults to all hang out together. When I booked I was more concerned about the sleeping area so I assumed there was a living room. The guest suite is in the basement of home in a nice neighborhood."
The price is NZ$419
includes taxes & fees
30 July - 31 July
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

Indoor Pool Paradise | 6BR + Huge Decks

The price is NZ$2,851
includes taxes & fees
29 July - 30 July
Indoor Pool Paradise | 6BR + Huge Decks

New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

10.0 out of 10, Exceptional, (25)
"A beautiful and bright cottage in a serene but convenient location. It was thoughtfully set up for a family getaway and was exceptionally clean. My entire family enjoyed the stay!"
The price is NZ$1,584
includes taxes & fees
27 July - 28 July
New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (9)
The House In Highland- Secluded Retreat

Our home is perfect for relaxing and having lots of fun, with near by activity’s

9.8 out of 10, Exceptional, (6)
"Really liked that each room had it's own temperature control"
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Cozy Cabin with Sauna & Firepit!

9.2 out of 10, Wonderful, (33)
"Excellent "
Cozy Cabin with Sauna & Firepit!

Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA

8.8 out of 10, Excellent, (5)
"Had a wonderful, relaxing stay here. Convenient location allowed us to walk everywhere we wanted to go!"
Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA

Hickory on Willow Lake

9.4 out of 10, Exceptional, (3)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is NZ$1,028
includes taxes & fees
29 July - 30 July
Hickory on Willow Lake

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

8.0 out of 10, Very good, (1)
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Simply Unforgettable HotTub, Pool, Pets, <1 Hr NYC

10.0 out of 10, Exceptional, (77)
"Lovely stay at large and clean home with great kitchen and pool area. Lots of room for everyone and attentive hosts"
Simply Unforgettable HotTub, Pool, Pets, <1 Hr NYC

Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train

9.4 out of 10, Exceptional, (3)
"We only stayed a couple days, but the location is quaint and apartment newly refurnished. The owner was very helpful and great to work with. Highly recommend!"
Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Philipstown Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Philipstown?

Yes, there are holiday rentals in Philipstown close to Manitoga The Russel Wright Design 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?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of Philipstown is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Philipstown?

Choose from 35 Expedia holiday rentals in Philipstown for a memorable holiday.

What can I see and do in Philipstown?

Enjoy the outdoors at Hudson Highlands State Park and Hudson River, or simply take in cultural attractions like Boscobel House and Gardens and Manitoga The Russel Wright Design Center. Other places in town to visit include Clarence Fahnestock State Park and West Point Foundry Preserve.

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.