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The Westchester Castle Ossining, NY

7 bedroom | 5 bathroom | House | From $450/night

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Welcome to The Westchester Castle! Looking for the best stay in Westchester this summer? Start your next adventure and step into the famous Westchester Castle. Our picturesque 5- Bedroom castle in the heart of the Lower Hudson Valley! Explore what the historic town of Ossining has to offer and get a full sense of upstate living!

Welcome to The Westchester Castle! Welcome to The Westchester Castle! Looking for the best stay in Westchester? Start your next adventure and step into the famous Westchester Castle. Our picturesque 5- Bedroom castle in the heart of the Lower Hudson Valley! Explore what the historic town of Ossining has to offer and get a full sense of upstate living!

Surround yourself with breathtaking mountain views, surrounded by complete peace and relaxation this summer. This is the quintessential family estate. The private, off-the-grid location will give you and your loved ones the chance to get away from it all and relax in a tranquil setting. The crystal-clear swimming pool will keep everyone cool during those hot summer days, while the gourmet kitchen will ensure that no one goes hungry. Don't miss out, book your stay today!

5-star ★★★★★ REVIEW: " 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 Environment. The hosts were fantastic and super responsive. The house was stunning with so much to do. We will 100% come back. Thanks again!" -- Aaron B.

Book now and receive our FREE Digital Guide App📱 - You’ll have access to everything you need to plan your stay!

— 🏡 ABOUT The Westchester Castle —
► 5 bedrooms (2 Queens, 4 Fulls, 1 Twin), 5 bathrooms ( Sleeps 13)
► FREE Private Wi Fi (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

The Westchester Castle is professionally managed by Pine (IG: @staywithpine ) 🌲, a luxury hospitality provider. We aim to make your stay a 5-STAR success!

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!

💥 BOOK NOW💥 and receive access to our DIGITAL GUIDE APP. You’ll have immediate access to a hand picked selection of restaurants, breweries, wineries, and other activities in and around Ossining after booking! Share with your guests and access any time from your phone! Have your activities planned out in advance – Just show up and start relaxing, you’ll have it all mapped out ahead of time. Need help finding the perfect hangout? We’re here to help. Below are some key spots that The Westchester Castle is in close proximity to in the Summer.
► Local Fine Dining, Restaurants and Breweries up and down the Hudson River
► Hiking
‎‏‏‎ ‎‏‏‎ ‎‏‏‎ ‎‏‏‎ ‎▷ Bear Mountain State Park
‎‏‏‎ ‎‏‏‎ ‎‏‏‎ ‎‏‏‎ ‎▷ Rockland Lake State Park
‎‏‏‎ ‎‏‏‎ ‎‏‏‎ ‎‏‏‎ ‎▷ New Croton
► Trump National Golf Course ( Westchester)
► Sing Sing Museum
► Shopping

5-star ★★★★★ REVIEW: " 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!" - Hazel G.

— KITCHEN 👨‍🍳 —
Be a chef in this custom gourmet kitchen with marble, granite, custom cabinetry, and breakfast room. The kitchen has everything you need to feel right at home in this charming and historic home. Whether you are looking to cook a meal from scratch or bring food to heat - this elegant kitchen is perfect for your weekend getaway or week-long stay.

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.

5-star ★★★★★ REVIEW: " 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." - Evan R

Q: On what floor are the beds located in the home? A: On the main level there are no bedrooms, all of the bedrooms are on the second and third floors.
Q: Is the home handicap accessible? No, there are no bedrooms that are handicap accessible.
Q: Is there a grill? There is no grill available at this time.
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? The home has central AC and heat.
Q: How can we contact you during the stay? A: The Westchester Castle is professionally managed by Pine Hospitality (IG: @staywithpine). You may contact Pine directly through the platform, by email, or via 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: 21 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: We are always open to events. Please contact us for any inquiries.
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 4PM. Check-out is at 11AM. Half-day extensions may be available upon request with an additional charge. There is no guarantee for early or late check-in/out requests 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 prior to your stay.

🎂 You must be at least 21 years of age to book at The Westchester Castle. A photo of your government ID is required after booking.

🧹 We take pride in preparing an exceptionally clean 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 very much hope you enjoy it. Any non-standard cleaning will result in an additional charge.

📷 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. 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.

🔊 To protect our great community and home from partiers or loud/disturbing guests, The Westchester Castle has a loud noise detection sensor installed. We love our neighbors and community, and want to continue providing a great place for you and future guests to stay!

🎫 A photo of your valid government identification is required within 24 hours after making your reservation. 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.

🆘 Due to the nature of living in an unpredictable world, we highly recommend you invest in travel insurance to protect yourself in any case of unforeseen circumstances. We strictly abide by our cancellation policy if you decide to cancel. If you are interested in travel insurance, two possible options may include Insure My Trip and Berkshire Hathaway Travel Protection. We do not have any affiliation or specific recommendation for these vendors.

👨‍💼 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.

Setting & View
  • Downtown
  • Golf Course Front
  • Mountain
Popular Amenities
  • Internet
  • Air Conditioning
  • Central Heating
  • Linens Provided
  • Towels Provided
  • Washing Machine
  • Clothes Dryer
  • Hot Water
  • Private Living Room
  • Hair Dryer
  • Iron & Board
  • Wifi
  • Ceiling Fans
  • Laptop Friendly Workspace
  • Basic Soaps
  • Paper Towels
  • Shampoo
  • Toilet Paper
  • Hangers
  • Private Entrance
  • Lock On Bedroom Door
  • Extra Pillows & Blankets
  • Kitchen
  • Refrigerator
  • Stove
  • Oven
  • Microwave
  • Dishwasher
  • Dishes & Utensils
  • Spices/ Pantry Items
  • Coffee Maker
  • Toaster
  • Freezer
  • Blender
  • Kettle
  • Pots & Pans
  • Dining Table
  • Desk
  • Office
  • Television
  • Satellite/ Cable
  • Games/ Board Games
  • Game Room
  • Pool Table
  • Smart TV
Pool/ Spa
  • Private Pool
  • Heated Pool
  • Fenced Pool
  • Deck/ Patio (uncovered)
  • Balcony/ Terrace
  • Lawn/ Garden
  • Veranda
  • Private Yard
  • Play Area
  • Adventure
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
  • Health/ Beauty Spa
  • Marina
  • Winery Tours
Sports & Adventure
  • Basketball Court
  • Cycling
  • Fishing
  • Golf
  • Hiking
  • Jet Skiing
  • Bird Watching
  • Eco Tourism
  • Horseback Riding
  • Outlet Shopping
  • Boating
  • Shopping
  • Carbon Monoxide Detector
  • Fire Extinguisher
  • First Aid Kit
  • Exterior Lighting
  • Smoke Detector
  • Enhanced Cleaning Practices
  • Cleaning Disinfection
  • Common Surface Disinfectant Cleaned
  • Linens High Temp Wash
  • Children's Dinnerware
  • Parking
  • Free Parking
  • Street Parking
  • Free Parking On Premises
  • Requires Stairs
  • Cameras/ Surveillance

Our Customers Love The Westchester Castle – You Will Too!