Cottages in Philipstown
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A serene lake surrounded by autumn foliage and trees.

Search Philipstown Cottage Rentals from CA $209

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your current months are November, 2026 and December, 2026.

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Our top choices for Philipstown cottages

A house with a view of a bridge and mountains.

A room with a wooden dresser, a mirror, a red chair, and a patterned rug.

A kitchen with a marble table, white chairs, wooden cabinets, a microwave, a toaster, and a clock on the wall.

A room with a telescope on a tripod near a window with a view of a mountainous landscape.

1. 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, (150 reviews)

9.8/10

Exceptional

(150 reviews)

"We had a great stay!!"

Jasmine

The price is CA $280

CA $280

CA $429 total

includes taxes & fees

Nov 16 - Nov 17

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

A two-story house with a balcony, surrounded by lush greenery.

A bedroom with a wooden bed, a red chair, a small bedside table, and a window with curtains.

A kitchen with a stove, oven, and white cabinets; a wooden staircase with a railing; and a green sofa.

A room with a skylight, a wooden desk, a green chair, a mirror, and a white cabinet.

2. Quiet Solitude with Firepit, Electric Stove & Private Deck

Quiet Solitude with Firepit, Electric Stove & Private Deck

Hopewell Junction

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"We enjoyed our stay at Sara's place. Unfortunately due to all the rain we couldn't enjoy the outside facilities. The bedroom loft is charming and everything you need is there. Thanks for a great stay!"

stephanie a.

The price is CA $229

CA $229

CA $765 total

includes taxes & fees

Nov 10 - Nov 11

Quiet Solitude with Firepit, Electric Stove & Private Deck

A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

A bedroom with a bed, two bedside lamps, a framed picture on the wall, and a door with a window.

A wooden deck with two white chairs and a small table, overlooking a lush green landscape.

A wall with a mirror, a hat, a picture, and a bag hanging on hooks.

3. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen

9.4 out of 10, Exceptional, (17 reviews)

9.4/10

Exceptional

(17 reviews)

"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."

Jessica C.

The price is CA $210

CA $210

CA $399 total

includes taxes & fees

Nov 12 - Nov 13

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

A wooden deck with a railing overlooking a body of water and trees.

A room with a wooden floor, a white door with glass panels, a wooden cabinet, and a dresser with decorative items.

A television on a windowsill with a view of trees and a river outside.

A kitchen with white cabinets, a stainless steel sink, a microwave, and a stove. There's a window with a view of trees and a framed artwork on the wall.

4. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Croton-on-Hudson

9.6 out of 10, Exceptional, (28 reviews)

9.6/10

Exceptional

(28 reviews)

"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "

Eva C.

The price is CA $353

CA $353

CA $570 total

includes taxes & fees

Nov 10 - Nov 11

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

A spacious living room with a fireplace, a ceiling fan, and a large window.

A single-story house with a covered porch, a small garden, and a paved driveway.

A rectangular swimming pool with a wooden deck and blue lounge chairs.

5. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Monroe

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"We loved our stay! It was the perfect size for our small family. The property was extremely well maintained and there was a lot to do near by. We would definitely book here again!"

Marc

The price is CA $233

CA $233

CA $741 total

includes taxes & fees

Nov 30 - Dec 1

Hudson Valley Retreat w/ Pool Near Greenwood Lake

A modern kitchen with white cabinets, granite countertops, a stainless steel refrigerator, and a wooden floor.

6. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake

3.0 star property

Monroe

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"The house was very quiet and exactly as advertised. Would stay again!"

Scott

The price is CA $300

CA $300

CA $762 total

includes taxes & fees

Nov 30 - Dec 1

Hudson Valley Retreat w/ Pool Near Greenwood Lake

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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Learn more about Philipstown

Head to sights like Boscobel House and Gardens and Hudson Highlands State Park as you discover Philipstown.

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Search Philipstown Cottage Rentals from CA $209

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Philipstown cottages

1. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

2. Quiet Solitude with Firepit, Electric Stove & Private Deck

3. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

4. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

5. Hudson Valley Retreat w/ Pool Near Greenwood Lake

6. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Learn more about Philipstown

Explore a world of travel with Expedia