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

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

A modern living room with a large window, a sofa with patterned cushions, a wooden coffee table, and a painting on the wall.
A spacious living room with a large window, a grey sofa with patterned cushions, and a wooden coffee table.
A Tudor-style house with a brick facade, a steeply pitched roof, and a large front yard with a paved patio and a stone wall.
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.
An outdoor dining area with string lights, candles, and floral centerpieces.

Reviews

8.8 out of 10
Excellent

Highlights

  • Firepit available
    One of the few properties with a dedicated outdoor firepit.
  • Discover nearby landmarks
    Close to Sing Sing Prison Museum

Popular amenities

  • Balcony
  • Private pool
  • Arcade/game room
  • Barbecue grill
  • Air-conditioning
  • Pet-friendly

Explore the area

View in a map
Ossining, NY
  • Place, Sing Sing Prison Museum
    ‪14 min walk‬
  • Place, Sing Sing Correctional Facility
    ‪18 min walk‬
  • Place, Louis Engel Waterfront Park
    ‪18 min walk‬
  • Airport, New York, NY (LGA-LaGuardia)
    ‪80 min drive‬

Rooms & beds

5 bedrooms (sleeps 13)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Double Bed

Bedroom 4

1 Double Bed

Bedroom 5

2 Double Beds

4 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Spaces

Kitchen
Balcony
Separate dining area
Garden
Dining area

Add dates for prices

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About the area

Ossining

Located in Ossining, this holiday home is near a water park. Captain Lawrence Brewing Company and Mohansic Golf Course are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Westchester County Center and Jacob Burns Film Center Theater. Looking to enjoy an event or a game while in town? See what's going on at Clover Stadium, or consider a night out at Travelers Rest. Take in the nearby slopes with snowboarding and skiing, or try out other outdoor activities such as ice skating and snowmobiling.
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Map
Ossining, NY

What's nearby

  • Nelson Park - 11 min walk - 1.0 km
  • Merchants Square - 13 min walk - 1.1 km
  • Sing Sing Prison Museum - 14 min walk - 1.2 km
  • Sing Sing Correctional Facility - 18 min walk - 1.5 km
  • Louis Engel Waterfront Park - 18 min walk - 1.5 km

Getting around

  • Ossining Station - 20 min walk
  • White Plains, NY (HPN-Westchester County) - 31 min drive

Restaurants

  • ‪Here Coffee + Beer - ‬20 min walk
  • ‪Sing Sing Kill Brewery - ‬12 min walk
  • ‪3 Westerly Bar and Grill - ‬3 min drive
  • ‪First Village Coffee - ‬15 min walk
  • ‪Ossining Pizzeria and Restaurant - ‬3 min drive

Frequently asked questions

Is Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!?

As of 25 Oct 2026, prices found for a 1-night stay for 2 adults at Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! on 25 May 2027 start from £5,126, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!?

On-site parking is available at the property.

What time is check-in at Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!?

Check-in begins at 4:00 PM.

What time is check-out at Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!?

Checkout is at 10:00 AM.

Where is Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! located?

Situated in Ossining, this holiday home is within 1 mile (2 km) of Sing Sing Prison Museum and Louis Engel Waterfront Park. Rockefeller State Park Preserve and Hardscrabble Wilderness Area are also within 6 miles (10 km). Ossining Station is 20 minutes by foot.

Reviews

8.8

Excellent

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 7 out of 10 reviews
Rating 8 - Good. 1 out of 10 reviews
Rating 6 - Okay. 1 out of 10 reviews
Rating 4 - Poor. 1 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

8.0/10

Cleanliness

9.6/10

Check-in

9.4/10

Communication

9.4/10

Location

8.0/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at this property and really enjoyed our time there. The house was very clean, comfortable, and well taken care of, which made us feel right at home. The host was also fantastic—very responsive, easy to communicate with, and always quick to answer any questions we had. Everything about the stay went smoothly from beginning to end. Overall, we had a great experience and would happily stay here again. We definitely recommend this property to anyone looking for a comfortable and enjoyable place to stay!
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Super fun location! Host was very helpful. The house is very comfortable for large groups
Stayed 5 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great communication before with both management property and property owner, space was very nice, rules were easy to follow, fantastic opportunity for visiting the area!
Stayed 2 nights in Oct 2025
Verified review

4/10 Poor

Liked: Check-in, communication, location
Technically the house was"clean" but it's grimy. The doors and floors all needed a deep clean. One of the showers had a curtain with red mold stains. The AC could not cool the upstairs properly, and the 3rd floor was excessively hot. The wall to wall carpet on the second floor was smelly. The living room was lacking seating for adults. I wouldn't recommend this house for a family get together, but maybe it would be fine for a bachelor party. The listing said there was one bedroom with a king. We never found it. All the beds seem to be queen size.The pool was clean and refreshing.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Communication was excellent. The house itself is older and fine for its age, but
Stayed 5 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A wonderful holiday stay in Westchester

We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again.
Stayed 4 nights in Dec 2024
Verified review

8/10 Good

Liked: Check-in, communication
Disliked: Cleanliness, location, listing accuracy

Spacious, good for groups, not very clean

The photos definitely misrepresent the quality of the property. The house is very dirty (lots of stains) and a little on the creepier side. However, if you have a good group of friends who can have fun anywhere, you’ll enjoy the rental.
Stayed 3 nights in Dec 2024
Verified review

6/10 Okay

Liked: Cleanliness, location
Disliked: Communication, listing accuracy

Unique Property, But Significant Downsides & Communication Issues

This is an incredibly unique property with some upsides. It is a cool old (1920's) Tudor style house that is well-suited for large groups. While it was fine for a couple of nights, any longer would have made the downsides (deferred maintenance, insufficient silverware, stained carpeting) less tolerable. There were also some communication issues with the property management company and the host during the stay. Specifically, we counted on there being a crib available, as it was specified in the listing. The owner offered to drop it off the next day - halfway through a two-day stay - which was disappointing. He never followed up on that offer. I was contacted by Hudson Valley Luxury Rentals (the company that manages the property) two days after our departure requesting a five-star review on VRBO. I sent a detailed reply through the VRBO app and by email. After getting no response, I emailed two addresses I found on HVLR's website. Still no reply. I consider this very poor customer service, especially for a so-called "luxury" rental company. I feel that I gave them sufficient time and the benefit of the doubt, and now I will be following up with VRBO directly. Despite the issues, the owner was prompt and communicative about a laptop that was left behind. For that, I was grateful.
Stayed 2 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Jun 2025
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