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Philipstown Vacation Rentals

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Vacation 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 CA $257
CA $418 total
includes taxes & fees
Jul 28 - Jul 29
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 CA $613
CA $806 total
includes taxes & fees
Aug 3 - Aug 4
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 CA $395
CA $857 total
includes taxes & fees
Jul 28 - Jul 29
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 CA $375
CA $485 total
includes taxes & fees
Jul 28 - Jul 29
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

Serene Hudson Valley Escape w/ Pool & Grill

10.0 out of 10, Exceptional, (1)
"An amazing stay in the 4th of July weekend- great place, double pool, giant rooms and everything in, included a patio for chillout, grilling and enjoy weekends with family and friends. Also, owners are nice, really kind and we definitely stay in touch for future escapes"
Serene Hudson Valley Escape w/ Pool & Grill

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

Magnificent Lake View

2.0 star property
Magnificent Lake View

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 CA $164
CA $346 total
includes taxes & fees
Jul 30 - Jul 31
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

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 CA $817
CA $1,295 total
includes taxes & fees
Aug 12 - Aug 13
New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

Indoor Pool Paradise | 6BR + Huge Decks

The price is CA $1,203
CA $2,420 total
includes taxes & fees
Jul 28 - Jul 29
Indoor Pool Paradise | 6BR + Huge Decks

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 CA $580
CA $842 total
includes taxes & fees
Aug 6 - Aug 7
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
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

Frequently asked questions

Can I find vacation rentals in Philipstown?

Yes, we offer vacation rentals in Philipstown near Manitoga The Russel Wright Design 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?

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

How many vacation rentals are there in Philipstown?

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

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 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.