Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Upstate New York Paradise at Westchester Castle: Your Sunny Group Getaway!

7 Bedrooms, 4 Bathrooms: Sleeps 13 with varied bed types for comfort.

Entertainment Galore: Smart TV, pool table, board games.

Modern Kitchen: Fully equipped for all culinary needs.

Relaxation: In-ground pool and indoor tub.

Convenience: Free 100 Mbps WiFi, self-check-in/check-out, washer & dryer.

Nearby Attractions: Close to parks, family spots, dining, and more!

Welcome to The Westchester Castle – your luxurious escape from the bustle of the city and a gateway to the very best of upstate New York.

This exquisite 6-bedroom, 7-bathroom estate boasts 6,000 sq. ft. of elegant living space and comfortably accommodates up to 13 guests. Whether you're relaxing by the private in-ground pool, unwinding at the fully stocked in-house bar, enjoying a BBQ with complimentary fuel, playing pool, or cozying up by one of the multiple fireplaces, every corner of this estate is designed for comfort and connection.

Perfect for families and pet lovers, the home is fully equipped with thoughtful amenities including a Pack ‘n Play, baby utensils, and a dog/cat bed.

Nestled just minutes from the historic town of Sleepy Hollow, you’ll find yourself surrounded by seasonal charm and natural beauty. Discover winter magic with nearby attractions like Rockefeller State Park Preserve, Croton Gorge Park, and Teatown Lake Reservation—all offering snowy paths, scenic trails, and cozy local gems. Whether you're planning a festive winter gathering or a peaceful seasonal escape, The Westchester Castle offers an unforgettable backdrop for every occasion.

— ABOUT THE WESTCHESTER CASTLE —
► 6 bedrooms (2 Queens, 4 Fulls, 2 Twin), 7 bathrooms (Sleeps 13)
► FREE Private WiFi (100 Mbps)
► Fully capable kitchen perfect for all stays!
► Smart TV - Access Netflix, Hulu, HBO and more!
► Self Check-In and Check-Out
► In-Ground Pool (Seasonal, Not Heated)
► Washer & Dryer
► Pool Table
► Pet Friendly!
► Custom full in-house bar
► 6000 ft² / 557 m²

— WHAT'S INCLUDED —
Just show up and drop the bags! The home is fully stocked and ready for you to enjoy. An example of items in the home include:
► BEDROOM: Sheets, Blankets, Pillows - feel right at home.
► BATHROOM: Towels, Shampoo, Conditioner, Soap, and other bathroom basics!
► KITCHEN: Salt, Pepper, Olive Oil, Coffee
► FREE Digital Guide App - Everything you need to plan your stay!

— NEARBY ATTRACTIONS AND RESTAURANTS —
Need help finding the perfect hangout? We're here to help. Below are some key spots that The Westchester Castle is near in the Winter.

— TOP ATTRACTIONS – FALL SEASON —
► Hike through vibrant fall foliage, enjoy birdwatching, and explore scenic trails at Rockefeller State Park Preserve (About 3 miles - 5 min. drive)

► Stroll through scenic gardens, walk along the Hudson River, and capture stunning foliage views at Croton Gorge Park (About 1 mile - 4 min. drive)

► Sleepy Hollow – Experience the spooky charm of fall with haunted hayrides, the Great Jack O'Lantern Blaze, and guided tours through the famous Sleepy Hollow Cemetery. (About 5 miles - 10 min. drive)

— NEARBY PARKS, HIKING, AND BIKING TRAILS —
► Arthur J. Jones Park (About 1 mile - 3 min. drive)
► Teatown Lake Reservation (About 4.5 miles - 10 min. drive)
► Kitchawan Preserve (About 6 miles - 10 min. Drive
► Croton Gorge Park (About 6 miles - 12 min. drive)

— NEARBY LOCAL CULTURE AND MUSEUMS —
► Ossining Recreation & Parks (About 1 mile - 4 min. drive)
► Lyndhurst Mansion (About 10 miles - 18 min. drive)
► LEGOLAND Discovery Center Westchester (About 15 miles - 20 min. drive)

— NEARBY EVENT CENTERS AND VENUES —
► The Briarcliff Manor (About 2 miles - 5 min. drive)
► Grace Hall Club (About 2 miles - 5 min. drive)
► Abigail Kirsch at Tappan Hill Mansion (About 7 miles - 15 min. drive)

— NEARBY SCHOOLS, COLLEGES, UNIVERSITIES —
► Westchester Community College Ossining (About 1.5 miles - 4 min. drive)
► SUNY Westchester Community College (About 9 miles - 14 min. drive)
► United States Military Academy (About 20 miles - 30 min. drive)

— NEARBY MARKETS, SHOPS, OUTLETS —
► La Placita Mini Market (About 1 mile - 3 min. drive)
► CTown Supermarkets (About 1 mile - 3 min. drive)
► ACME Markets (About 1 mile - 3 min. drive)

— GOLF COURSES NEARBY —
► The 19th Hole Indoor Golf, Bar and Restaurant (About 1 mile - 3 min. drive)
► Hudson Hills Golf Course (About 4 miles - 10 min. drive)
► Trump National Golf Club Westchester (About 4 miles - 10 min. drive)

— WINERIES AND BREWERIES —
► Sing Sing Kill Brewery (About 0.5 miles - Walking distance)
► Here Coffee + Beer (About 1 mile - 3 min. drive)
► Prospero Winery & Home Winemaker Depot (About 5 miles - 12 min. drive)

— NEARBY TOP BREAKFAST LOCATIONS —
► First Village Coffee (About 0.5 miles - Walking distance)
► DD's Diner (About 1 mile - 3 min. drive)
► The Tasty Table (About 1 mile - 3 min. drive)

— NEARBY TOP LUNCH LOCATIONS —
► Lucy's Pizza (About 0.5 miles - Walking distance)
► Los Abuelos Restaurant (About 1 mile - 3 min. drive)
► Brothers Fish & Chips (About 1 mile - 3 min. drive)

— NEARBY TOP DINNER LOCATIONS —
► Aji Limo Peruvian Cuisine (About 0.5 miles - Walking distance)
► 3 Westerly Bar and Grill (About 1 mile - 3 min. drive)
► The Boathouse (About 0.5 miles - 3 min. drive)

— LOCATION AND PARKING —
The Westchester Castle is located in the quiet village of Ossining, NY. Only 49 minutes to NYC! Right next to the parkways. 15 minutes to White Plains. Restaurants, bars, and venues within 10-minutes of driving. Easily access all of the Hudson River towns in beautiful upstate New York! FREE private parking is available directly in front of the home. The home has a private driveway with parking for up to 5 vehicles.

— FREQUENTLY ASKED QUESTIONS —
Q: On what floor are the beds located in the home? A: On the main level, there are no bedrooms; all the bedrooms are on the second and third floors.
Q: Is the home handicap accessible? A: No, there are no bedrooms that are handicap accessible.
Q: Is there a grill? A: Yes, with FREE fuel.
Q: Are pets allowed? Up to 2 dogs are allowed. A pet fee of $35/night per pet will apply.
Q: Does the home have Air Conditioning (AC) and heat? A: The home has central AC and heat.
Q: How can we contact you during the stay? A: The Westchester Castle is professionally managed by Hudson Valley Luxury Resorts. You may contact us through the platform, email, or the dedicated customer service line.
Q: What is the cancellation policy? A: The cancellation policy is unique to every reservation. Please review the terms on the website.
Q: What is the minimum age to book? A: 25 years of age
Q: Why do you require a photo of my government identification? A: We require your ID for compliance with our insurance. Your ID is kept private and is not shared with anyone.
Q: Can I host an event or celebration at The Westchester Castle? A: No
Q: When will the pool be open? A: The pool is weather dependent. We aim to open the pool in spring each year and close it in the early fall. Contact us to confirm availability!

— THINGS TO KNOW - Please read before you book! —
► Check-in is at 4 PM. Check-out is at 10 AM. Half-day extensions may be available upon request with an additional charge. There is no guarantee for early or late check-in/out or half-day requests. Changes to these times are based on availability and the schedule of our cleaning teams.

► The Westchester Castle is self-check-in and self-check-out. The home has a lockbox that you may use to enter the home. The code will be provided before your stay.

► MINIMUM AGE: You must be at least 25 years of age to book at The Westchester Castle. A photo of your government ID is required after booking.

► CLEANLINESS: We take pride in preparing a spotless and prepared home for your visit! The Westchester Castle is cleaned, sanitized, and restocked before/after every guest. Please respect our space, treat it as you would your home, and keep it clean! Our team is dedicated to providing a clean space for our guests, and we very much hope you enjoy it. Any non-standard cleaning will result in an additional charge.

► MONITORING: To protect our guests and home, The Westchester Castle has a camera installed at the front door ONLY. We do NOT spy on our guests. The recording is motion-activated and only captures activity outside the front door. No cameras or monitoring devices exist inside the property. Content is not shared with third parties unless required by insurance or law.

► GOVERNMENT ID REQUIRED: A photo of your valid government identification is required 48 hours before your check-in date. WE RESERVE THE RIGHT TO CANCEL A RESERVATION AT ANY TIME IF YOU DO NOT PROVIDE YOUR ID. CANCELLATIONS ARE SUBJECT TO THE CANCELLATION POLICY.

► By booking this listing, you give permission to the property manager to use a third party to screen my identity and check criminal databases to confirm my reservation. Complete terms regarding the guest screening can be provided by the property manager. You may receive an email to complete your screening. Please check your spam inbox for this email and contact the property manager if you have any questions.

► This location has an additional apartment with tenants. The apartment is separate from the main home. During your stay, there may be other cars in the driveway.
You are in our home, treat it as if it were yours!
Quiet hours: 11PM to 8AM
Check-In: 4PM, Check-Out 10AM
No Smoking — $1500 penalty for deep cleaning
Up to 2 dogs are allowed. A pet fee of $35/night per pet will apply.
No parties or events — $1500 minimum penalty for unauthorized events
Do not rearrange the furniture.
Keep the kitchen tidy & clean all dishes!
Minimum age to book: 28+
Maximum occupants: 13 - Only booked guests are allowed on the property

Left-behind items are a $50 + shipping fee, we are not responsible if an item cannot be found.