Ossining is home to this holiday home. Sing Sing Prison Museum and Jacob Burns Film Center Theater are cultural highlights, and some of the area's activities can be experienced at Hilltop Hanover Farm and Environmental Center and Captain Lawrence Brewing Company. Travelling with kids? Consider Westchester County Center and Chappaqua Performing Arts Center. Take the opportunity to explore the area for water adventures such as power boating.
Ossining Historical Society - 2 min drive - 1.5 km
Croton Point Park - 8 min drive - 8.1 km
Van Cortlandt Manor - 8 min drive - 7.8 km
Westchester County Center - 22 min drive - 19.8 km
Bear Mountain State Park - 31 min drive - 33.3 km
Getting around
Ossining Station - 10 min drive
White Plains, NY (HPN-Westchester County) - 26 min drive
Restaurants
105-Ten Bar & Grill - 3 min drive
Brothers Fish & Chips - 5 min drive
Ossining Pizzeria and Restaurant - 17 min walk
Yalla Halal - 4 min drive
Starbucks - 3 min drive
Frequently asked questions
Is Snow Days & City Escapes: Spacious Ossining Home pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Snow Days & City Escapes: Spacious Ossining Home?
As of 28 Oct 2026, prices found for a 1-night stay for 2 adults at Snow Days & City Escapes: Spacious Ossining Home on 9 Nov 2026 start from £1,101, 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 Snow Days & City Escapes: Spacious Ossining Home?
On-site parking is available at the property.
What time is check-in at Snow Days & City Escapes: Spacious Ossining Home?
Check-in begins at 4:00 PM.
What time is check-out at Snow Days & City Escapes: Spacious Ossining Home?
Checkout is at 10:00 AM.
Where is Snow Days & City Escapes: Spacious Ossining Home located?
This family-friendly Ossining holiday home is within 3 mi (5 km) of Sing Sing Prison Museum and Louis Engel Waterfront Park. Jacob Burns Film Center Theater and Chappaqua Performing Arts Center are also within 6 miles (10 km).
Reviews
8.2
Very good
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
A family trip with teens and tweens- a perfect space! Clean, hist was friendly, the house was stocked with all we'd need! A great getaway for any family NYC trip!
Stayed 3 nights in May 2026
Response from VrboOwner on 13 Jun 2026
Thank you so much for the wonderful review, Justeen!
We’re thrilled to hear that your family had a great stay and that the home was a perfect fit for your trip with teens and tweens. It’s great to know you found the house clean, well-stocked, and comfortable, and that our hospitality helped make your getaway enjoyable.
We truly appreciate you choosing our home as your base for exploring NYC and creating family memories together. We’d love to host you and your family again anytime your travels bring you back to the area!
Safe travels and thank you again for your kind words!
Best regards,
Oscar
Lots of stairs but I think that's typical for this area. The parking/driveway is tight. Couldn't pull our SUV in to the garage due to tight angles and backing out onto curvey road is a little rough but again, I think it's typical for the area. The house is spacious and well kept. Nice location!
Stayed 3 nights in Aug 2026
Response from VrboOwner on 28 Aug 2026
We're glad you found the home spacious, well kept, and in a nice location! As a hillside property, the home does have stairs and a longer driveway. The driveway is wide enough for two vehicles to park side by side and loops around, allowing guests to turn around before exiting rather than backing onto the road. The garage can accommodate a minivan or standard-sized SUV, though larger vehicles may not fit comfortably. We appreciate you sharing your experience and hope you enjoyed your stay overall.
We had a wonderful time visiting NY for my 2 grandchildren’s graduation celebrations. The house was spacious & very comfortable for our family of 11 & my sweet pup. If the opportunity comes again to visit NY this house would be 1st on our list. Thank you for sharing your home with us.
Stayed 4 nights in Jun 2026
Response from VrboOwner on 17 Aug 2026
We're so glad the house was a comfortable home base for your family during such a special trip celebrating your grandchildren's graduations. It's wonderful to hear the space worked well for a group of 11, and that your pup felt welcome too since we love being pet-friendly. Thank you for sharing this with us and for taking such good care of the home during your stay.
From the owner: "Thank you for the review! I really appreciate you taking the time to share your feedback. It was a pleasure hosting you, and I’m glad communication met your expectations. You’re always welcome back, and I hope to host you again in the future!"
Comfortable stay. Loved the game/TV room in the basement, perfect for our teens to entertain in a different area. I also loved that there were 4 toilets for our family trip. Communication with the host was smooth and quick! Definitely recommend.
Stayed 7 nights in Nov 2025
Response from VrboOwner on 3 Dec 2025
From the owner: “Hi, Thank you so much for your kind review! We’re really glad to hear your family had a comfortable stay and that the game/TV room was a hit with the teens. We’re also happy the layout of the home worked well for your trip. It was a pleasure hosting you, and we truly appreciate your recommendation. You’re welcome back anytime! Safe travels, and thanks again!”
This was our Christmas gathering place for family from 4 states. Beautiful home and location.
Stayed 4 nights in Dec 2024
From a partner site
10/10 Excellent
Paul
1 Jul 2025
Great stay in Ossining
Great house and location. Lots of amenities and comfortable furniture. Great backyard (with fireflies if you're there in the summer). Lots of space with a fun basement/gameroom. We recommend!
Response from VrboOwner on 18 Jul 2025
Hi Paul,
Thank you so much for the kind words and recommendation! I’m thrilled to hear you enjoyed the house, especially the backyard and game room — and yes, the fireflies are such a magical summer touch! I’m glad the space and amenities made for a comfortable stay. You’re welcome back anytime!
Warmly,
Family funeral brought us to the area. House was excellent for us
Stayed 3 nights in Nov 2024
From a partner site
10/10 Excellent
Julia
20 Mar 2026
Massive house with foosball table for family fun
This house is massive! I opened a door expecting it to be a garage. It wasn't: it was a huge 5th bedroom! It was clean and we really appreciated that the refrigerator was totally empty (we're so used to having other people's condiments left in fridges). We are so appreciative that he allowed our rotten chihuahua-mix join us. Thank you! The owner was so responsive and flexible and the location was ideal. We loved going to First Village Coffee and recommend it.We had so much fun with the foosball table, and playing hide-and-seek with the rotten chihuahua.
Response from VrboOwner on 24 Mar 2026
Hi Julia,
Thank you so much for the wonderful review—it truly means a lot! I’m really glad you enjoyed the space (that “surprise” 5th bedroom gets a lot of people) and that everything felt clean and ready for your stay.
I’m especially happy your chihuahua-mix was able to join the fun—we love hosting guests traveling with their pups.
Great call on First Village Coffee too—that’s one of our favorites! And it sounds like the foosball table and hide-and-seek made for some great memories.
You and your group were an absolute pleasure to host, and you’re always welcome back anytime.
All the best,
Oscar
Verified review
8/10 Good
Joyce S.
19 Aug 2025
Liked: Cleanliness, check-in, communication
Great house, not great for neighborhood walking. Absolutely need a car to get around.
Stayed 28 nights in Jul 2025
Response from VrboOwner on 26 Aug 2025
From the Owner: "Thank you so much for staying with us for nearly a month — we truly appreciate it! We’re so glad you and Stanley enjoyed the house. You’re absolutely right that having a car is the best way to get around the neighborhood, and your note will be very helpful for future guests. It was a pleasure hosting you both, and we’d love to welcome you back anytime your travels bring you this way."
This house was wonderful! Had a lot of space and it was perfect. Feliciano was very receptive, even helped open the door remotely for me when I had a hard time getting in at check in. Responded immediately. Would book again!
Great communication with the property manager, Oscar. Super, prompt, responsive and helpful. I didn’t know when I booked thru VRBO that it would switch to EVOLVE and that there was a one time extra charge to VRBO, very confusing and adds to total cost.
Stayed 3 nights in Oct 2025
Response from VrboOwner on 20 Oct 2025
Hi Pam,Thank you so much for your kind words! I really appreciate you taking the time to share your experience. I’m glad I could help make your stay smooth and enjoyable. I completely understand the confusion around the VRBO and Evolve booking process — it can definitely be unclear at times. I’ll be sure to pass along that feedback to help make things more transparent for future guests.It was a pleasure hosting you, and you’re always welcome back anytime!Warm regards,Oscar
The house was nice & spacious. I do feel like it could use more seating in the living room, considering it can hold up to 11 guests. It would aslo be nice if there were tv's in the guest rooms upstairs. Also, maybe make sure the cleaning crew removes cobweks.
Stayed 4 nights in Sep 2024
Response from VrboOwner on 19 Sept 2024
From the owner:Hi Heidi, thank you for your feedback on your recent stay! We are thrilled you enjoyed the property. We'd like to take a moment to raise the concerns you mentioned. -We take great care in thoroughly cleaning our properties, but as you may know, spiders can form webs quite quickly—even within a few hours or overnight—especially in more natural environments. While we do our best to stay on top of this, we will make sure to pay even closer attention to this detail moving forward.-Regarding your suggestions about additional seating and TVs in the guest rooms, we appreciate your input and will certainly take it into consideration as we continually work to enhance the experience for our guests.Thanks again for choosing our home, and we hope to have the opportunity to host you again in the future!
Nice house for a big family or 2 families. The air was a bit stale like no one had used it for a while and they didnt air it out before we arrived. Also the dryer would not dry, it was styck on cool no matter what setting we put. All in all, a great place to stay
We had a group of 6 close friends traveling to NY to visit another friend who lives in Cortland Manor. This house was in exactly the right location and had the right amenities for our group. Everyone had their own bedroom and there were enough bathrooms for folks to have a little privacy. The beds are comfy and there’s a ton of space in this house. Our only issue was the lack of furniture in almost every room. No coffee table in the living room is a problem when you have 8 people hanging out together. There are no luggage racks of surfaces to put your bags. Otherwise, its a great house.
Overall our stay was nice. Unfortunately the dryer did not work. We tried everything to get our clothes to dry and had to take them home wet. Wanted to wash more towels but dryer not heating. Listing states there was an iron and ironing board but there was not. We had to go out and purchase both as we were there to attend multiple wedding events. There is no gym only an exercise weigh bench in garage.
House was beautiful, well kept and all rooms were clean, comfortable and nice.
The worst VRBO experience ever:We arrived in NY anticipating a wonderful stay, this was our third time bringing guests to tour.Our days are usually filled with activities outside of the residence and we like to return in the evening and share a meal together, fellowship, and to enjoy the comforts of a home environment. This is why we choose VRBO over staying at a hotel.After the drive in from JFK, we arrived at our VRBO, 18 Somerstown Rd. Ossining, NY. We choose rooms, and headed back out the door to do a little grocery shopping and to bring in a meal for the night here is a list of our shared experience:Trash was all over the area where it seemed trash was kept. None of the trash cans had lids, only one trash can was really available for our use.It looked like an animal had rummaged through the trash, the critter had easy access to trash, nothing prevented him or them, no deterrent.The was refrigerator was NOT clean. We had to wipe it down.Next black carpenter ants were every where.Ants were in beds, all over kitchen, on walls, bathrooms, everywhere.The shower head in the master bedroom did not function well, making taking a shower difficult. We could not get water temperature adjusted.Also the tub was not clean.The upstairs shower needed/needs a new shower curtain, the one there is filthy.There was no soap of any kind available to shower with, if not provided this should have been mentioned.One of the amenities listed was washer/dryer for the first fe
Stayed 8 nights in Apr 2025
Response from VrboOwner on 29 Jul 2025
From the Owner: "Hi Vanessa, thank you for taking the time to share your experience. I want to sincerely apologize for the condition of the property during your stay—it’s clear that we fell far short of the quality and comfort you expected and deserved.-Please know that we’ve taken your feedback very seriously. Since your visit, we have replaced both the host and the cleaning team responsible for the property to ensure a much higher standard moving forward. We’ve also addressed the issues you mentioned, including proper trash disposal, pest control, deep cleaning of the kitchen and bathrooms, and refreshing amenities like shower curtains and supplies.-We understand how disappointing this experience must have been—especially as you were hosting guests and looking forward to a relaxing home environment. I truly regret that we weren’t able to provide that for you.-We appreciate your honesty and hope you’ll consider giving us another chance in the future. Your feedback has been instrumental in helping"
Verified review
4/10 Poor
Mussie B.
27 Jul 2026
Stayed 3 nights in Jul 2026
Response from VrboOwner on 11 Aug 2026
Thank you for staying with us. We’re sorry that your experience did not meet your expectations. During your stay, we were actively communicating with you regarding the air conditioning and worked to provide solutions and alternatives while the area was experiencing an extreme heatwave. We understand that the unusually high temperatures and resulting discomfort affected your experience, and we regret that. We appreciate your feedback and will continue working to ensure our guests have a comfortable stay.
Our A/C was working fine, but the area was experiencing an extreme heat wave, which wasn’t working properly to keep up with the heat.