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Philipstown Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Philipstown

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

Vacation Home in Fishkill

9.6 out of 10, Exceptional, (49)
"Nice place"
United States
mary B.
The price is ￥42,647
￥54,383 total
includes taxes & fees
Dec 5 - Dec 6
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Interior
Large,Cozy,Bright Apartment, Business Themed.

Vacation Home in Newburgh

9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is ￥66,995
￥106,433 total
includes taxes & fees
Dec 6 - Dec 7
Large,Cozy,Bright Apartment, Business Themed.
Exterior
Rustic Cabin in Fishkill!

Cabin in Fishkill

10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is ￥46,912
￥70,101 total
includes taxes & fees
Dec 8 - Dec 9
Rustic Cabin in Fishkill!
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Cottage in Fort Montgomery

9.8 out of 10, Exceptional, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is ￥29,155
￥47,720 total
includes taxes & fees
Dec 5 - Dec 6
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Terrace/patio
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Vacation Home in Highland

9.4 out of 10, Exceptional, (10)
"Enjoyed the stay. Nice place to relax for a weekend."
United States
Marie J.
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Property grounds
Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in Newburgh

9.4 out of 10, Exceptional, (30)
"A very cute, convenient, and affordable stay with timely, friendly communication from the owner. Our dog loved it and we appreciated the ability to have a private place to stay."
United States
Sara B.
The price is ￥20,005
￥30,960 total
includes taxes & fees
Dec 7 - Dec 8
Cabin in the heart of the Hudson Valley, Cabin 2
Property grounds
Wappinger Cottage - Scandinavian retreat on a creek

Cottage in Poughkeepsie

10.0 out of 10, Exceptional, (23)
"This was the perfect get away spot! Serene location, lovely amenities, and a gracious host."
United States
Laurie C.
Wappinger Cottage - Scandinavian retreat on a creek
Outdoor dining
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Cottage in Croton-on-Hudson

9.6 out of 10, Exceptional, (15)
"We enjoyed our overnight stay at this quaint nicely appointed carriage house."
United States
Cathleen C.
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Outdoor dining
The House In Highland- Secluded Retreat

Vacation Home in Highland

10.0 out of 10, Exceptional, (18)
"Very nice location and private."
United States
Patrick P.
The House In Highland- Secluded Retreat
Children's area
Hickory on Willow Lake

Vacation Home in Fishkill

9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
United States
Rachel C.
The price is ￥59,706
￥85,628 total
includes taxes & fees
Dec 29 - Dec 30
Hickory on Willow Lake
Interior
Luxury 9BR Retreat w/Pool & Hot Tub

Villa in Chester

7.0 out of 10, Good, (2)
"Pool was not open or usable but we were not interested in doing that "
United States
John D.
Luxury 9BR Retreat w/Pool & Hot Tub
Interior
Contemporary Cozy Cottage

Vacation Home in Lake Peekskill

10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥34,893
￥65,096 total
includes taxes & fees
Dec 8 - Dec 9
Contemporary Cozy Cottage
Terrace/patio
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Vacation Home in Newburgh

10.0 out of 10, Exceptional, (21)
"Great host, amazing area, perfect get away!"
United States
Gianna W.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Property grounds
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Apartment in Wallkill

10.0 out of 10, Exceptional, (70)
"Everything was great nexactly as advertised. Terrific stargazing at night by the fire pit. Will definitely come back."
United States
David C.
The price is ￥17,865
￥36,337 total
includes taxes & fees
Dec 7 - Dec 8
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Fridge, microwave, oven, stovetop
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Villa in Monroe

6.8 out of 10, (5)
"It was a great home with lots of space indoor and outside. "
United States
Yogita R.
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Exterior
Mountain View escape

Cottage in New Paltz

10.0 out of 10, Exceptional, (68)
"We had a wonderful time at Mountain View! It was the perfect escape for a birthday unplug with the best pup. The kitchen had everything we needed to make meals and feel right at home. Can’t wait to come back. "
United States
Caitlin G.
Mountain View escape
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cabin in Carmel

3.0 star property
10.0 out of 10, Exceptional, (3)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
United States
Varuna S.
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Smart TV
Grant - A Tranquil One Bedroom Steps from River

Apartment in Newburgh

9.6 out of 10, Exceptional, (39)
"Stan is really nice and helpful. The apartment is really well designed, spacious and clean, very well equipped with a nice porch. Stan is really thoughtful. Recommended!"
United States
Zohar
The price is ￥16,823
￥40,354 total
includes taxes & fees
Dec 15 - Dec 16
Grant - A Tranquil One Bedroom Steps from River
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Vacation Home in Poughkeepsie

10.0 out of 10, Exceptional, (2)
"Great host"
United States
Lindsey F.
The price is ￥25,557
￥90,055 total
includes taxes & fees
Dec 7 - Dec 8
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Interior
Modern 4BR Home on 10 Acres Family & Pet-Friendly Retreat Near New Paltz

Vacation Home in Highland

10.0 out of 10, Exceptional, (26)
"Beautiful newer house in a beautiful spacious property. Fully equipped and nicely decorated!! My family had an amazing weekend celebrating family. "
United States
Laura
Modern 4BR Home on 10 Acres Family & Pet-Friendly Retreat Near New Paltz
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

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"Nice place great staff"
Irvin 1-night trip
Posted 17 hours ago
Hampton Inn Harriman Woodbury

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
  • Use the map to find apartments and other holiday homes in the Philipstown neighbourhood you prefer
  • 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 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 a coffee maker, 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 26 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 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.