Autumnal Family Retreat | 5BR Castle with Game Room & Pool

House in Hudson Valley, Ossining
  • Sleeps
  • Bedroom(s)
  • Bathroom(s)
    4 full, 1 half
  • $550 - $700



Nestled within the picturesque embrace of Hudson Valley, Westchester Castle is an enchanting autumnal haven, inviting you to experience the season's splendid embrace. This captivating estate, reminiscent of a fall fairytale, offers ample space for cherished family gatherings or intimate escapes. Revel in the regal ambiance as you luxuriate in your private pool amidst a backdrop of autumnal hues, and savor the warmth of the season within the confines of our charming in-house bar and lounge area.

Westchester Castle is pet-friendly and kid-friendly—so feel free to bring the whole gang along!

 The Grand foyer leads to a custom gourmet kitchen with marble, granite, custom cabinetry, breakfast room with views and doors to deck. Dramatic sunken living room with 10' ceiling and marble fireplace, columns, and transom windows overlooking the village.

Formal dining room with onyx and granite fireplace. Family room with access to deck, home office. Sweeping staircase with hand-carved railing to master suite with marble fireplace and bath, balcony; three additional bedrooms and hall bath. A staircase leads to the "Sky Lounge" with a media room, custom wet bar room, skylights, and 2nd office. Finished lower level with living room, bedroom, full bath, and 2nd laundry, walk-out to patio. Come outside to the balcony and look at the night stars and just relax to end the perfect day. Breathtaking mountain views, surrounded by complete peace and relaxation. This Mansion offers the best of the best in the Hudson Valley. Come enjoy the crystal-clear swimming pool and outdoor scenery. Then come on back in to your mosaic grand living area with flat-screen TV's and a game room.

Walk upstairs to your custom in-house bar... the perfect feature for any special occasion. Listen to music or just enough the mount view from the top floor! Enjoy some drinks and get to sleep on our magnificent king beds. This listing gives you complete access to the Main House (5 bed 5 bath, 4 floors, dining room, kitchen, 2 living rooms, a sky lounge on the 3rd floor, a full bar and in-ground pool / Parking.

The resort includes an in-house laundry machine and a workstation for your business needs! The perfect getaway!! Come book today! Perfect for long stays.


Accommodation, Features

Property Type
House, 5,000 sq. ft.
5 Bedroom(s), 12 Sleeps
King: 1
Queen: 3
Sleep Sofa: 2
Twin / Single: 1
4 Bathroom(s) (1 Half bathrooms)
Combination Tub / Shower: 1
Half Bath: 1
Jetted Tub: 1
Tub: 1
Walk-in Shower: 3
Location Type
Mountain View
Vacation Types
Away From It All
Large Events-Wedding/Reunions
Off-Grid Vacation Rentals
Pet Friendly
Tourist Attractions
Year-Round Vacation Rentals
Access & Parking
Secure Parking
CD Player
Game Room
Pool Table
Satellite / Cable
Popular Amenities
Air Conditioning
Clothes Dryer
Deck / Patio
Dining Area
Fitness Room / Equipment
Hot Tub
Linens Provided
Outdoor Grill
Towels Provided
Washing Machine
Wireless Internet
Indoor Features
Activities / Restaurant Guide
Coffee Maker
Cooking Utensils
Dishes & Utensils
Hair Dryer
Ice Maker
Iron & Board
Jetted Bath Tub
Living Room
Pantry Items
Outdoor Features
Deck / Patio
Lawn / Garden
Outdoor Charcoal Grill
Outdoor Furniture
Private Pool
Terrace / Balcony
Activities & Adventure
Eco Tourism
Outlet Shopping
Rock Climbing
Sight Seeing
Wildlife Viewing
Nearby Attractions
Botanical Garden (20 miles)
Churches (1 miles)
Cinemas (10 miles)
Gambling Casinos (20 miles)
Library (2 miles)
Marina (10 miles)
Miniature Golf (3 miles)
Museums (5 miles)
Outlet Shopping (10 miles)
Restaurants (3 miles)
Theme Parks (30 miles)
Winery Tours (5 miles)
Zoo (35 miles)

Additional Property Information

Best Hudson Valley Vacation rental you will EVER find. GUARANTEED! The scenery is impeccable, the house is breath-taking and there is nothing else like it. Escape the city or traveling from another country, it has the vibes for any type of family or experience. The stay will be like no other. Super close to Up-state NY and NYC within distance too. The perfect location for your New York Travels.


September 2023
November 2023
December 2023
February 2024
  • Not available
  • Pending
  • Available
  • No Rates Set


-Nightly rateWeekly rateMonthly rateMin. StayChange-over
Rate summary $550 - $700 $4,000 $13,000 1 Nights -

Fees, Taxes, Deposit

TypeTypePriceCharge Type
Cleaning FeeRequired $300One time


Check in: 14:00 / Check out: 10:00
Payment options
Visa, Maestro, Mastercard, American Express, Discover, Paypal, Venmo, Zelle, Cash, Wire transfer, Western Union, Checks, eCheck
Be respectful. No smoking inside the property. Please take care of everything and treat it as it was your home. We want you to have fun and enjoy yourself, just do the right thing.
Additional Info
Great for Long stays- blazing fast wifi, at-home working station. Everything you need for a one day adventure or a 3 month long trip! Come book with us now!
Cancellation Policy
You can cancel for a FULL-refund up until 24 hours of the check in date. Just notify us that you want to cancel, we are flexbile.
Pet Friendly: Yes, pets welcome
Smoking: No smoking
Children: Yes, great for kids
Long term rentals: Yes
Seniors: Yes
Wheelchair Accessible: No
Suitability Details
This Castle is a perfect lifestyle for young, medium and old. Pet and Kid Friendly environment is what we provide. Great for long term stays and business professionals. Access to local buses, training and dining. Everything you need to have a great time!

About the Owner

Young Entrepreneurs that started in the Hudson Valley Region. We live for creating great experiences for others. We thrive off seeing people happy and having a good time. We created this brand to allow people to live luxury without having to pay for "luxury" prices. All you need in one house. Come check out our other locations as you travel.

12 Reviews

Autumnal Family Retreat | 5BR Castle with Game Room & Pool
The Westchester palace was a remarkable resort.

The Westchester palace was a remarkable resort. Not only did we get some time to relax, it had everything to get work done as well. The perfect Enviorment. The hosts were fantastic and super responsive. The house was stunning with so much to do. We will 100% come back. Thanks again

Stayed September, 2021

Autumnal Family Retreat | 5BR Castle with Game Room & Pool
We will be back! Thanks again.

My family and I had an incredible time at your sprawling place. Convenient location, soft bedding, and well-stocked furniture. We will be back! Thanks again.

Stayed September, 2021

Autumnal Family Retreat | 5BR Castle with Game Room & Pool
Hosts were very attentive

Hosts were very attentive, accommodating us having young kids, gave us a tour of facility, and provided for all of our needs!

Stayed September, 2021

Autumnal Family Retreat | 5BR Castle with Game Room & Pool
Definitely a fun home!

Definitely a fun home!

Stayed September, 2021

Autumnal Family Retreat | 5BR Castle with Game Room & Pool
Amazing, amazing, amazing house

Amazing amazing amazing house the house was beautiful
Jake was an amazing host
great at communicating and making sure we had everything we needed

Stayed September, 2021

Autumnal Family Retreat | 5BR Castle with Game Room & Pool
Everything was clean and organized.

The house was amazing. Everything was clean and organized. Jake communicated very quickly and we were always able to contact him. My group and I had a great time and we look forward to returning next year and making it a yearly event. Book it!

Stayed August, 2021

Autumnal Family Retreat | 5BR Castle with Game Room & Pool
Just what we needed to have a relaxing week away!

Jakes house is amazing! Just what we needed to have a relaxing week away! A few things to know before booking as they may be a deal-breaker for some but were not a huge issue for us is: (may be temporary) the only bedroom with a TV currently is the master bedroom which could be an issue if you have children with you and although you have the whole main house there is an apartment with someone living there as well as another unit off to the side currently occupied as well. Like I said not an issue for us but for some it may be. Both occupants were friendly and the pool was only accessible to us. Overall an amazing stay and would stay again!

Stayed August, 2021

Autumnal Family Retreat | 5BR Castle with Game Room & Pool
The owners were very accommodating and helpful if we ever needed anything.

This house was amazing. It is huge and has everything a person or group of people could ever need - tons of bedrooms complete with balconies, a master suite with an awesome shower and hot tub, a large pool with a basketball hoop and lifeguard stand, billiards, TVs, etc. The owners were very accommodating and helpful if we ever needed anything. We didn't experience any issues and would highly recommend this to anyone interested!

Stayed July, 2021

Autumnal Family Retreat | 5BR Castle with Game Room & Pool
We had the best stay!!

Thank you for inviting us to your home, Jake. Very beautiful and comfortable, indeed! We had the best stay!! We will forever cherish the beautiful memories and the coolest moments we had while in Million $ Mansion Hudson Valley Villa!

Stayed July, 2021

Autumnal Family Retreat | 5BR Castle with Game Room & Pool
This is a charming property

This is a charming property right in the heart of a wealth of New York history. There are endless things to do nearby, if you are so adventurous or curious, or plenty of perks to get you to just stay in and enjoy the amenities this property offers. When staying with a family, it definitely offers something for everyone.

Stayed July, 2021

7791 View(s) Last update: 18-Sep-2023 10:27

Contact the Owner

Your Information

Tell us about your trip:

If your dates are flexible select approximate travel dates to help speed up the process.

Message to owner:

Fields marked with * are mandatory
$550 - $700 $4,000 $13,000
Select Dates for an Instant Quote
and Request to Book Online

Booking request