Town of Philipstown, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Philipstown, New York on RentalSaver.com!

Town of Philipstown Rentals

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VRBO
Castle by the Lake
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
This one-of-a-kind castle with modern rustic charm is the perfect getaway for movie nights by the fireplace, curling up ...
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VRBO
From $1057 per night (USD)
Expedia
Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to Coppermine House in Garrison I hope you enjoy your stay. 10 mins across the river from West Point Academy, 1 ...
From $1057 per night (USD)
Expedia
From $604 per night (USD)
VRBO
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Natural surroundings blend with modern living at this spacious Garrison vacation rental! The 3-bedroom, 2.5-bathroom mod ...
From $604 per night (USD)
VRBO
From $348 per night (USD)
VRBO
Updated Home w/ Patio Half Mile to West Point
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Hudson River haven is perfect for your next visit to Highland Falls! Whether you’re here to visit a loved one at We ...
From $348 per night (USD)
VRBO
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VRBO
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This charming historic home is located only 2 blocks from Thayer Gate at the United States Military Academy at West Poin ...
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VRBO
From $347 per night (USD)
Expedia
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Nestled just above charming Main Street, this freshly updated 2-bedroom apartment is the perfect home base for families ...
From $347 per night (USD)
Expedia
From $581 per night (USD)
VRBO
Panoramic Hudson Valley Views at Romantic and Private Mountainside Estate
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Only one mile from Beacon's thriving Main St., yet completely secluded and away from any neighbors, this is a gorgeous g ...
From $581 per night (USD)
VRBO
From $736 per night (USD)
Expedia
Bear Mountain House.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to our cozy Garrison cottage steps to Anthony's Nose hiking trail, minutes from the Bear Mountain bridge, 15 min ...
From $736 per night (USD)
Expedia
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VRBO
Swimming in the hudson highlands in your own super private woodland sanctuary.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Come unwind in our beautifully renovated California Contemporary home. The home sits at the end of a private 6 house str ...
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VRBO
From $321 per night (USD)
Expedia
West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to your stylish retreat in the heart of Highland Falls! This charming 2-bedroom apartment boasts breathtaking mo ...
From $321 per night (USD)
Expedia
From $1152 per night (USD)
VRBO
Modern Luxurious Country Retreat w/ Sauna + Hot tub 1hr from NYC
Bedrooms:
1
Bathrooms:
5
Sleeps:
10
Escape to a serene modern ranch-style country house and guest cottage nestled on 4 private acres, just 1 hour from NYC. ...
From $1152 per night (USD)
VRBO
From $2368 per night (USD)
VRBO
COZY RETREAT : HOT TUB, SAUNA, POOL + MORE
Bedrooms:
2
Bathrooms:
5
Sleeps:
14
PLEASE DO NOT BOOK FOR WP GRADUATION. A request must be made first. Welcome to your home away from home in Garrison. ...
From $2368 per night (USD)
VRBO
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VRBO
Hudson Valley Heaven | a wooded oasis with modern amenities awaits you
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
A chefs and hikers dream house! Sink right into your private, wooded oasis on nearly 7 acres backing into the forest on ...
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VRBO
From $388 per night (USD)
Expedia
Bright/modern escape :: nestled in the forest, walk to the village & train
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Modern, efficiently and elegantly constructed (Passive House Standards) private flexible garden apt. guesthouse can be u ...
From $388 per night (USD)
Expedia
From $543 per night (USD)
VRBO
Modern Farmhouse Walking Distance to West Point
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come stay in this newly renovated home with original details and decorated with modern day charm. Walking distance to We ...
From $543 per night (USD)
VRBO
From $829 per night (USD)
Expedia
1780 Hudson Valley Farmhouse
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Our historic farmhouse is the perfect Hudson Valley retreat. The home is sun drenched with mountain views out every win ...
From $829 per night (USD)
Expedia
From $431 per night (USD)
VRBO
Cozy House 3 Blocks From West Pt
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to this thoughtfully remodeled Historic 1890s home, just steps away from West Point's Thayer Gate. The house is ...
From $431 per night (USD)
VRBO
From $596 per night (USD)
VRBO
Cold Spring Getaway | Saltwater Pool & Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Imagine yourself surrounded by nature, with a glorious view of the Hudson Highlands and private saltwater pool. Our retr ...
From $596 per night (USD)
VRBO
From $492 per night (USD)
VRBO
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Escape to a stylish 3BR cottage with a private pool (available summer season), cinema room, game room, and fire pit, per ...
From $492 per night (USD)
VRBO
From $40 per night (USD)
VRBO
Willow Lane Country RV SITE ONLY - sewer+water+metered elec
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Beautiful RV SITE ONLY in Cold Spring. On environmentally conscious farm w/ solar energy, and fresh delicious well wate ...
From $40 per night (USD)
VRBO
From $161 per night (USD)
VRBO
Cozy Cold Spring Getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This cozy 1 bedroom pet friendly garage apartment is tucked away in the Hudson Valley forest on a private road. You will ...
From $161 per night (USD)
VRBO
From $391 per night (USD)
VRBO
Relaxing Lake Retreat in Cold Spring
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to Valhalla Highlands, a peaceful retreat located just one hour from NYC and only ten minutes from Cold Spring v ...
From $391 per night (USD)
VRBO
From $192 per night (USD)
VRBO
Local Artist Inspired | Walk to WestPoint + King Bed
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This unique place has a style all its own. Local Artist Inspired with a modern feel that's walking distance to West Poin ...
From $192 per night (USD)
VRBO
From $143 per night (USD)
Expedia
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to West Point! Stay at our quiet, cozy, and private apartment in the heart of Highland Falls. Walkable to West P ...
From $143 per night (USD)
Expedia
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VRBO
House on the Babbling Brook - 2m to West Point
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Relax to the the sounds of the flowing brook in this beautiful, restored pre-civil war era home. Veteran owned, 3 mins ...
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VRBO
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Expedia
Cold Spring Private Suite - 2 min from train
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Room in a guest suite Your own room in a home, plus access to shared spaces. Great for remote work Fast wifi at 69 Mbps, ...
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Expedia
From $1107 per night (USD)
VRBO
Historic home at West Point on Main Street. 1 mile from Thayer Gate!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Charming Historic Home with modern amenities near West Point Military Academy. 4 bedrooms upstairs , 1 full bath upstai ...
From $1107 per night (USD)
VRBO
From $274 per night (USD)
VRBO
Charming Cold Spring Village Home
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover the charm of the Hudson Valley from your own historic cottage, just five minutes from the train, one hour from ...
From $274 per night (USD)
VRBO
From $577 per night (USD)
VRBO
Modern West Point House near USMA - 3 bed, 2 bath with Hot tub & Fire pit!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
In the picturesque town of Highland Falls, you'll find this cozy three-bedroom retreat perfect for your relaxing holiday ...
From $577 per night (USD)
VRBO
From $452 per night (USD)
Expedia
Contemporary Cozy Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The modern contemporary cozy cottage has been completely renovated with an electric fireplace, ceiling fan/light, large ...
From $452 per night (USD)
Expedia
From $495 per night (USD)
VRBO
Hudson Valley's Nature Experience with Incredible Views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Historic Cold Spring, 1 hour from N.Y.C on Metro North Our spacious home on 2 acres boasts a large fully equipped Eat in ...
From $495 per night (USD)
VRBO
From $309 per night (USD)
Expedia
Lovely 3BR Home with parking-Walk to WP Gate!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Walk to West Point! Enjoy the Hudson Valley. Bring the whole family to this great place with lots of room for fun. Cozy ...
From $309 per night (USD)
Expedia
From $336 per night (USD)
VRBO
Walk to WP Gate + Free Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy stylish comfort at this centrally located 2 Bedroom apartment. This charming second-floor walkup in a 2-family hou ...
From $336 per night (USD)
VRBO
From $477 per night (USD)
VRBO
Charming Highland Falls Home < 2 Mi to West Point!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Discover the Hudson Valley with this Highland Falls vacation rental as your home base! Situated less than 2 miles from W ...
From $477 per night (USD)
VRBO
From $511 per night (USD)
VRBO
Cold Spring Mountain Retreat: Secluded Autumn Oasis
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Your next mountain retreat is a short drive away from the bustling village of Cold Spring and approximately 90 minutes f ...
From $511 per night (USD)
VRBO
From $360 per night (USD)
VRBO
Idyllic farmhouse retreat in lower Hudson Valley, hiking trails steps away!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Escape to a beautifully restored 1900 farmhouse in the Lower Hudson Valley, just an hour from NYC, steps away from hikin ...
From $360 per night (USD)
VRBO
From $353 per night (USD)
VRBO
Charming 3-bedroom house.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Nestled in Cortlandt, this delightful house is a hidden gem waiting to be discovered by guests. With its quaint charm an ...
From $353 per night (USD)
VRBO
From $827 per night (USD)
Expedia
West Point Family Retreat, 5 min walk to Thayer!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
*Graduation 2025, 2026, 2027, 2028 & 2029 and Ring Weekend 2025, 2026, 2027 & 2028 are booked!* Relax in this well ap ...
From $827 per night (USD)
Expedia
From $400 per night (USD)
VRBO
Discover Nature’s Glory! Perfect Family Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Rustling trees, fresh mountain air, and all the time in the world to just slow down and enjoy it. This is everything NY ...
From $400 per night (USD)
VRBO
From $368 per night (USD)
VRBO
Walk to West Point from this 2-bedroom charmer
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience the beauty of the Hudson River Valley in this charming, mid-century home. Complete with a full kitchen, dinin ...
From $368 per night (USD)
VRBO
From $542 per night (USD)
VRBO
Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
The Space Set on 1.3 acres on a quiet country road and surrounded by woods, this spacious 5 bedroom, 2.5 bath, 2,700 SF ...
From $542 per night (USD)
VRBO
From $531 per night (USD)
Expedia
Room for Everyone: Spacious 6BR West Point Retreat
Bedrooms:
4
Bathrooms:
6
Sleeps:
15
Welcome to our Grand Serene 6-bedroom, 4-bathroom retreat nestled in the heart of Highland Falls, NY, Minutes to West Po ...
From $531 per night (USD)
Expedia
From $485 per night (USD)
VRBO
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Step into serene comfort at our newly constructed 3-bedroom, 2 bathroom (1,228 sqft) Top Floor unit nestled in the neigh ...
From $485 per night (USD)
VRBO
From $412 per night (USD)
VRBO
A well-appointed cottage in the woods of Garrison, NY
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to Forest Farm Retreat. Just minutes from Cold Spring and an hour from NYC, this getaway is perfect for family g ...
From $412 per night (USD)
VRBO
From $245 per night (USD)
VRBO
3BR West Point Retreat-3min to Back Gate+ King Bed
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Relax to the the sounds of the flowing brook in this beautiful, restored pre-civil war era home. Tucked away on a dead e ...
From $245 per night (USD)
VRBO
From $471 per night (USD)
Expedia
5 BR West Point Family Compound- Sleeps 10!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Relax to the the sounds of the flowing brook in this beautiful, restored pre-civil war era home. Tucked away on a dead e ...
From $471 per night (USD)
Expedia
From $920 per night (USD)
VRBO
West Point Mountain House
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to West Point and enjoy early check in & late check out at this beautiful mountainside house overlooking the vil ...
From $920 per night (USD)
VRBO
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Expedia
Garrison Woods Getaway: Main House - Cheery Mountain Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Garrison Woods Getaway, where joy waits around every corner. Whether you’re snuggling in for a board game or ...
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Expedia
From $372 per night (USD)
VRBO
2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to this delightful condo in picturesque Garrison. With 2 queen beds spread across 3 levels, with kitchen, laundry ...
From $372 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Fabulous 3bdrm Home w/parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Your family will be close to everything when you stay at this centrally located home. Easy access to West Point Gate and ...
From $328 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to this updated and centrally located ground floor apartment that is completely private. Walking distance from W ...
From $258 per night (USD)
VRBO
From $581 per night (USD)
VRBO
Home: 2 Mi to Thayer Gate at U.S. Military Academy
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Multiple Living Areas | Stargazing | 2 Mi to Hudson River | In-Unit Laundry There’s plenty of breathing room for the wh ...
From $581 per night (USD)
VRBO
From $537 per night (USD)
VRBO
Garrison Retreat | Trails & Stream
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to the Garrison Retreat, an exclusive retreat in the heart of the Hudson Valley. Set behind stately stone pillar ...
From $537 per night (USD)
VRBO
From $1285 per night (USD)
VRBO
Garrison Getaway | Pool, Sauna & Gym
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to the Garrison Getaway – Your Ideal Summer Retreat! Just one hour from NYC and five minutes from the charming v ...
From $1285 per night (USD)
VRBO
From $590 per night (USD)
VRBO
Cold Spring Village Maisonette with Pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Imagine stepping off the train in the picturesque Village of Cold Spring and strolling up scenic Main Street to your pri ...
From $590 per night (USD)
VRBO
From $137 per night (USD)
VRBO
Cozy House on the hill
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
***This is a ground level unit, the ceilings are low just about 6ft in some places lower-like the shower***. Stay comfo ...
From $137 per night (USD)
VRBO
From $194 per night (USD)
VRBO
Cozy 1-bedroom retreat minutes from West Point!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy easy access to everything from this perfectly located home base. Explore the beautiful Hudson Valley, shop the out ...
From $194 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Tranquil 4-bedroom home, 2 miles from West Point, loaded with amenities
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Located in Highland Falls, this comfort house offers 4 bedrooms with a mix of 1 king, 2 full, and 1 twin beds. The 2 bat ...
From $436 per night (USD)
Expedia

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Town of Philipstown Rentals

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Results: 58 Rentals