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Search Vacation Homes in Philipstown

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Our top choices for Philipstown vacation homes

Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
$458 nightly
The price is $464
Dec 20 - Dec 21
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
3 bedrooms, iron/ironing board, travel crib, WiFi
"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
2.0 star property
Holmes
9.6 out of 10, Exceptional, (4)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
$479 nightly
The price is $541
Dec 22 - Dec 23
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
$228 nightly
The price is $258
Dec 14 - Dec 15
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
$328 nightly
The price is $355
Dec 15 - Dec 16
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Property grounds
Quaint & Cozy Cottage | Wood Stove, Pet Friendly

Quaint & Cozy Cottage | Wood Stove, Pet Friendly

Quaint & Cozy Cottage | Wood Stove, Pet Friendly
New Paltz
10.0 out of 10, Exceptional, (3)
"Lovely home in a beautiful area of New York state. Would stay here again! "
United States
Jason W.
$469 nightly
The price is $525
Dec 15 - Dec 16
Total with taxes and fees
Quaint & Cozy Cottage | Wood Stove, Pet Friendly
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

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, (5)
$339 nightly
The price is $357
Dec 19 - Dec 20
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
Interior
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
2.0 star property
Warwick
10.0 out of 10, Exceptional, (5)
$323 nightly
The price is $365
Dec 14 - Dec 15
Total with taxes and fees
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.6 out of 10, Exceptional, (49)
"Inside was very nice, outside could use some curb appeal. Enjoyed our stay "
United States
Karen K.
$282 nightly
The price is $318
Dec 14 - Dec 15
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Dining
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
10.0 out of 10, Exceptional, (58)
"Clean and comfortable accommodations, very close to Legoland and Castle Fun Center! The kids loved the room with bunk beds, and it had a big selection of children's books and some toys, which was a nice bonus!"
United States
Jennifer K.
$466 nightly
The price is $487
Jan 4 - Jan 5, 2026
Total with taxes and fees
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Private kitchen
Tranquil 4-bedroom house in welcoming Poughquag neighborhood

Tranquil 4-bedroom house in welcoming Poughquag neighborhood

Tranquil 4-bedroom house in welcoming Poughquag neighborhood
2.0 star property
Poughquag
$257 nightly
The price is $291
Dec 15 - Dec 16
Total with taxes and fees
Tranquil 4-bedroom house in welcoming Poughquag neighborhood
Interior
Contemporary Cozy Cottage

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
$395 nightly
The price is $452
Dec 29 - Dec 30
Total with taxes and fees
Contemporary Cozy Cottage
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
10.0 out of 10, Exceptional, (2)
"Great host"
United States
Lindsey F.
$508 nightly
The price is $595
Dec 15 - Dec 16
Total with taxes and fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Interior
Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7)
"Convenient location. Nice to have 3 queen beds. One parking space is in a lot, but street for any additional. Plenty of availability though. Excellent washer and dryer, dishwasher. Internet worked well. "
United States
Matt D.
$263 nightly
The price is $295
Dec 22 - Dec 23
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.0 out of 10, Wonderful, (4)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
$255 nightly
The price is $278
Dec 14 - Dec 15
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
Property grounds
3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
7.6 out of 10, Good, (5)
"We were supposed to check out at 10 AM, and everyone was still sleeping. But at 8 AM, very loud noises suddenly started. It felt like the whole roof was shaking and the house might fall down. We went outside and saw that workers were cleaning the roof. No one told us anything about this before. When we asked the cleaning manager, he said the landlord booked this cleaning two weeks ago, but we, the guests, were never informed. Also, our car was parked in the driveway, and the things falling from...
United States
Lixing
$425 nightly
The price is $481
Dec 21 - Dec 22
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
Property grounds
Scenic View - WiFi - Fire Pit - Near Legoland, Woodbury Commons and the Castle

Scenic View - WiFi - Fire Pit - Near Legoland, Woodbury Commons and the Castle

Scenic View - WiFi - Fire Pit - Near Legoland, Woodbury Commons and the Castle
2.0 star property
Monroe
$394 nightly
The price is $445
Dec 22 - Dec 23
Total with taxes and fees
Scenic View - WiFi - Fire Pit - Near Legoland, Woodbury Commons and the Castle
Property grounds
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
wallkill
9.8 out of 10, Exceptional, (57)
"Loved this property, clean, wonderful view of the river. Quite neighborhood. Great location "
United States
Mamie G.
$337 nightly
The price is $378
Dec 14 - Dec 15
Total with taxes and fees
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Interior
Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.
Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
$409 nightly
The price is $483
Dec 14 - Dec 15
Total with taxes and fees
Large,Cozy,Bright Apartment, Business Themed.
Property grounds
Fun, Friends, and Family Lakefront Home w/Dock and Beach

Fun, Friends, and Family Lakefront Home w/Dock and Beach

Fun, Friends, and Family Lakefront Home w/Dock and Beach
Mahopac
10.0 out of 10, Exceptional, (12)
"Super convenient location :)"
United States
Sean M.
$672 nightly
The price is $728
Dec 15 - Dec 16
Total with taxes and fees
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Private kitchen
3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.

3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.

3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.
Goshen
8.0 out of 10, Very Good, (1)
"The check-in process went smoothly. The property was very clean and comfortable. Location was close to many different small towns. "
United States
Kelly M.
$398 nightly
The price is $490
Dec 14 - Dec 15
Total with taxes and fees
3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.
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

Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

10/10 Excellent
"Very good "
David E. 2-night trip
Posted 2 days ago
Sonesta Simply Suites Nanuet

Find out more about Philipstown

Philipstown Vacation Homes information

Number of reviews
274
Accommodation
318 Vacation Homes
Lowest Price
$258
Highest Price
$728

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