Entire home
Sleepy Hollow - Upstate Castle - BBQ Events Games
Photo gallery for Sleepy Hollow - Upstate Castle - BBQ Events Games
Reviews
9.69.6 out of 10
Exceptional
Entire home
7 bedrooms5 bathroomsSleeps 13398 sq m
Popular amenities
- Washer
- Pool
- Outdoor Space
- Pet friendly
- Barbecue grill
- Parking available
The price is SAR 3,756
SAR 3,756
SAR 5,904 total
includes taxes & fees
17 Nov - 18 Nov
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Sleepy Hollow - Upstate Castle - BBQ Events Games
Welcome to Westchester Castle: A Luxurious Summer Retreat in Ossining, New York!
Immerse yourself in the grandeur of Westchester Castle, a luxury estate in the picturesque town of Ossining, New York. Just steps away from Croton Bay and the Hudson River, this opulent property boasts seven bedrooms and accommodates up to 13 guests, making it an ideal getaway for families, friends, or special gatherings. With four exquisite bathrooms and a fully stocked kitchen, guests can enjoy comfort and convenience throughout their stay.
Westchester Castle offers upscale amenities to enhance every aspect of your stay. Relax in the soothing waters of the indoor tub, enjoy evenings gathered around the fire pit, or challenge companions to playful competition in the fully equipped game room. For culinary enthusiasts, an outdoor BBQ awaits, perfect for hosting delightful meals in a serene setting.
The castle's strategic location provides easy access to various local attractions. Nature lovers can explore nearby gems like the Rockefeller State Park Preserve and the scenic trails of Teatown Lake Reservation. Those interested in cultural activities will find the Van Cortlandt Manor and Lincoln Depot Museum just a short drive away. Additionally, shopaholics can enjoy luxury shopping experiences at nearby centers featuring brands like Gucci and Louis Vuitton.
With many family-friendly tourist spots close by, such as Croton Gorge Park and Kensico Dam Plaza, there are plenty of opportunities to create lasting memories. Golf enthusiasts can enjoy nearby courses, including the prestigious Trump National Golf Club Westchester. Local wineries and breweries like Chilmark Wines & Spirits and Captain Lawrence Brewing Company are must-visit locations for those who appreciate fine wines and craft beers.
Situated within walking distance of local markets and top-rated dining options, guests at Westchester Castle can easily access everything they need. Start your day with breakfast at Las Americas, enjoy a pizza lunch at Lucy's Pizza, and dine on exquisite Peruvian cuisine at Aji Limo for dinner—without needing a car.
Whether visiting during the vibrant spring season or as summer nears, Westchester Castle provides a luxurious base from which to enjoy the area's natural beauty and abundant activities. Perfect for short-term and mid-term stays, this property also welcomes events like birthdays and weddings, offering the space and atmosphere needed for spectacular celebrations.
Experience luxury, comfort, and convenience at Westchester Castle, where every detail is carefully curated to ensure an unforgettable stay. Whether you're looking for a peaceful retreat or a place to celebrate a special occasion, this Ossining estate promises a unique and enriching experience in the heart of New York's Hudson Valley.
— ABOUT THE WESTCHESTER CASTLE —
► 7 bedrooms (2 Queens, 4 Fulls, 1 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 TOURIST SPOTS —
► Rockefeller State Park Preserve (6 min. drive)
► Louis Engel Waterfront Park (5 min. drive)
► Teatown Lake Reservation (11 min. drive)
► Croton Point Park (12 min. drive)
► Scenic Hudson RiverWalk Park at Tarrytown (14 min. drive)
► Chilmark Village Park (Walking distance)
► Henry Gourdine Park (5 min. drive)
— NEARBY BEACH AND LAKES —
► Teatown Lake Reservation (11 min. drive)
► Silver Lake Park and Beach Croton (14 min. drive)
► Pocantico Lake (11 min. drive)
— NEARBY MUSEUMS AND CULTURAL ACTIVITIES —
► Van Cortlandt Manor (10 min. drive)
► New Castle Historical Society (16 min. drive)
► Lincoln Depot Museum (16 min. drive)
— LUXURY AND HIGH-END SHOPPING CENTERS —
► Gucci (19 min. drive)
► Louis Vuitton White Plains Westchester (19 min. drive)
► COACH (19 min. drive)
► Emporio Armani (18 min. drive)
— FAMILY-FRIENDLY TOURIST SPOTS —
► Croton Gorge Park (13 min. drive)
► Pierson Park (15 min. drive)
► Kensico Dam Plaza (16 min. drive)
— GOLF COURSES NEARBY —
► Trump National Golf Club Westchester (10 min. drive)
► Hudson Hills Golf Course (11 min. drive)
► Mohansic Golf Course (16 min. drive)
— WINERIES AND BREWERIES —
► Chilmark Wines & Spirits (Walking Distance)
► Here, Coffee + Beer (Walking Distance)
► Sing Sing Kill Brewery (12 min. drive)
► Soul Brewing Company (13 min. drive)
► Captain Lawrence Brewing Company (16 min. drive)
— NEARBY MARKETS —
► La Placita Mini Market (Walking Distance)
► ACME Markets (4 min. drive)
► Green’s Natural Foods (7 min. drive)
— TOP-RATED BREAKFAST LOCATIONS —
► Las Americas (Walking Distance)
► The Tasty Table (4 min. drive)
► DD's Diner (5 min. drive)
— TOP-RATED LUNCH LOCATIONS —
► Lucy's Pizza (Walking Distance)
► Los Abuelos Restaurant (4 min. drive)
► 3 Westerly Bar and Grill (5 min. drive)
— TOP-RATED DINNER LOCATIONS —
► Aji Limo Peruvian Cuisine (Walking Distance)
► Churrasqueira Ribatejo (Walking Distance)
► Makondo Restaurant Ossining (Walking Distance)
— 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: We are always open to events. Please get in touch with 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 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
Immerse yourself in the grandeur of Westchester Castle, a luxury estate in the picturesque town of Ossining, New York. Just steps away from Croton Bay and the Hudson River, this opulent property boasts seven bedrooms and accommodates up to 13 guests, making it an ideal getaway for families, friends, or special gatherings. With four exquisite bathrooms and a fully stocked kitchen, guests can enjoy comfort and convenience throughout their stay.
Westchester Castle offers upscale amenities to enhance every aspect of your stay. Relax in the soothing waters of the indoor tub, enjoy evenings gathered around the fire pit, or challenge companions to playful competition in the fully equipped game room. For culinary enthusiasts, an outdoor BBQ awaits, perfect for hosting delightful meals in a serene setting.
The castle's strategic location provides easy access to various local attractions. Nature lovers can explore nearby gems like the Rockefeller State Park Preserve and the scenic trails of Teatown Lake Reservation. Those interested in cultural activities will find the Van Cortlandt Manor and Lincoln Depot Museum just a short drive away. Additionally, shopaholics can enjoy luxury shopping experiences at nearby centers featuring brands like Gucci and Louis Vuitton.
With many family-friendly tourist spots close by, such as Croton Gorge Park and Kensico Dam Plaza, there are plenty of opportunities to create lasting memories. Golf enthusiasts can enjoy nearby courses, including the prestigious Trump National Golf Club Westchester. Local wineries and breweries like Chilmark Wines & Spirits and Captain Lawrence Brewing Company are must-visit locations for those who appreciate fine wines and craft beers.
Situated within walking distance of local markets and top-rated dining options, guests at Westchester Castle can easily access everything they need. Start your day with breakfast at Las Americas, enjoy a pizza lunch at Lucy's Pizza, and dine on exquisite Peruvian cuisine at Aji Limo for dinner—without needing a car.
Whether visiting during the vibrant spring season or as summer nears, Westchester Castle provides a luxurious base from which to enjoy the area's natural beauty and abundant activities. Perfect for short-term and mid-term stays, this property also welcomes events like birthdays and weddings, offering the space and atmosphere needed for spectacular celebrations.
Experience luxury, comfort, and convenience at Westchester Castle, where every detail is carefully curated to ensure an unforgettable stay. Whether you're looking for a peaceful retreat or a place to celebrate a special occasion, this Ossining estate promises a unique and enriching experience in the heart of New York's Hudson Valley.
— ABOUT THE WESTCHESTER CASTLE —
► 7 bedrooms (2 Queens, 4 Fulls, 1 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 TOURIST SPOTS —
► Rockefeller State Park Preserve (6 min. drive)
► Louis Engel Waterfront Park (5 min. drive)
► Teatown Lake Reservation (11 min. drive)
► Croton Point Park (12 min. drive)
► Scenic Hudson RiverWalk Park at Tarrytown (14 min. drive)
► Chilmark Village Park (Walking distance)
► Henry Gourdine Park (5 min. drive)
— NEARBY BEACH AND LAKES —
► Teatown Lake Reservation (11 min. drive)
► Silver Lake Park and Beach Croton (14 min. drive)
► Pocantico Lake (11 min. drive)
— NEARBY MUSEUMS AND CULTURAL ACTIVITIES —
► Van Cortlandt Manor (10 min. drive)
► New Castle Historical Society (16 min. drive)
► Lincoln Depot Museum (16 min. drive)
— LUXURY AND HIGH-END SHOPPING CENTERS —
► Gucci (19 min. drive)
► Louis Vuitton White Plains Westchester (19 min. drive)
► COACH (19 min. drive)
► Emporio Armani (18 min. drive)
— FAMILY-FRIENDLY TOURIST SPOTS —
► Croton Gorge Park (13 min. drive)
► Pierson Park (15 min. drive)
► Kensico Dam Plaza (16 min. drive)
— GOLF COURSES NEARBY —
► Trump National Golf Club Westchester (10 min. drive)
► Hudson Hills Golf Course (11 min. drive)
► Mohansic Golf Course (16 min. drive)
— WINERIES AND BREWERIES —
► Chilmark Wines & Spirits (Walking Distance)
► Here, Coffee + Beer (Walking Distance)
► Sing Sing Kill Brewery (12 min. drive)
► Soul Brewing Company (13 min. drive)
► Captain Lawrence Brewing Company (16 min. drive)
— NEARBY MARKETS —
► La Placita Mini Market (Walking Distance)
► ACME Markets (4 min. drive)
► Green’s Natural Foods (7 min. drive)
— TOP-RATED BREAKFAST LOCATIONS —
► Las Americas (Walking Distance)
► The Tasty Table (4 min. drive)
► DD's Diner (5 min. drive)
— TOP-RATED LUNCH LOCATIONS —
► Lucy's Pizza (Walking Distance)
► Los Abuelos Restaurant (4 min. drive)
► 3 Westerly Bar and Grill (5 min. drive)
— TOP-RATED DINNER LOCATIONS —
► Aji Limo Peruvian Cuisine (Walking Distance)
► Churrasqueira Ribatejo (Walking Distance)
► Makondo Restaurant Ossining (Walking Distance)
— 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: We are always open to events. Please get in touch with 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 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
Property amenities
Ski
- Close to skiing
Pool/Spa
- Private pool
Internet
- Free WiFi, with speed of 500+ Mbps (good for 6+ people or 10+ devices)
Parking and transportation
- Onsite parking options include a garage
- Onsite parking
- Car required
Kitchen
- Refrigerator
- Stovetop
- Microwave
- Oven
- Dishwasher
- Spices
- Toaster
- Coffee/tea maker
- Kitchen island
Dining
- Dining table
Bedrooms
- 7 bedrooms
- Bed sheets provided
Bathrooms
- 4.5 bathrooms
- Hair dryer
- Towels provided
Living spaces
- Fireplace
- Living room
- Dining room
Entertainment
- Smart TV
- Pool or billiards table
- Arcade/game room
- Books
- Games
Outdoor areas
- Balcony
- Fenced yard
- Barbecue grill
- Garden
- Firepit
Laundry
- Washing machine and dryer
- Near laundromat
Work spaces
- Desk
- Desk chair
Comfort
- Air conditioning
- Heating
Pets
- Pet friendly
Suitability/Accessibility
- Smoke-free property
Services and conveniences
- Iron/ironing board
Location highlights
- Near a health or beauty spa
- Near a hospital
- Near outlet shopping
Things to do
- Water park
- Golf privileges
- Water sports equipment
- Rafting nearby
- Swimming nearby
- Mountain biking nearby
- Power boating nearby
- Sledding nearby
- Wildlife and game walks nearby
- Birdwatching nearby
- Windsurfing nearby
- Winery tours nearby
Safety features
- Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
- Smoke detector installed (host has indicated there is a smoke detector on the property)
- Fire extinguisher
- First aid kit
General
- Unit size: 4284.0 sq ft (398 sq m)
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Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 18
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Pets
Pets allowed
Service animals are welcome, and are exempt from fees
Children and extra beds
Children are welcome
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events are allowed on site
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
We should mention
A car is required for transportation to and from this property
Property is also known as
252410
About the neighborhood
Ossining, NY
What's nearby
- Sing Sing Correctional Facility - 15 min walk
- Rockefeller State Park Preserve - 6 min drive
- Van Cortlandt Manor - 7 min drive
- Sleepy Hollow Cemetery - 9 min drive
- Thomas J. Watson Research Center - 13 min drive
Getting around
- Ossining Station - 18 min walk
- Westchester County Airport (HPN) - 31 min drive
Restaurants
- McDonald's - 3 min drive
- Here Coffee and Beer - 18 min walk
- Sing Sing Kill Brewery - 12 min walk
- 3 Westerly Bar and Grill - 4 min drive
- First Village Coffee - 15 min walk
Frequently asked questions
Is Sleepy Hollow - Upstate Castle - BBQ Events Games pet-friendly?
Yes, pets are allowed at this property.
What time is check-in at Sleepy Hollow - Upstate Castle - BBQ Events Games?
Check-in begins at 4:00 PM.
What time is check-out at Sleepy Hollow - Upstate Castle - BBQ Events Games?
Check-out is at 10:00 AM.
Where is Sleepy Hollow - Upstate Castle - BBQ Events Games located?
This family-friendly Ossining vacation home is within a 15-minute walk of Old Croton Aqueduct State Park and Sing Sing Correctional Facility. Sing Sing Prison Museum and Ossining Historical Society are also within 2 mi (3 km). Ossining Station is 18 minutes by foot.
Sleepy Hollow - Upstate Castle - BBQ Events Games Reviews
Reviews
9.6
Exceptional
90 external reviews
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