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NYC-Area Escape Near River, Trails & MTA!

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Ossining Vacation Rental | 5BR | 3.5BA | 2,800 Sq Ft | Stairs Required
Patio | Gas Grill | Gas Fire Pit
Game Room | Twin Sleeper Sofa | Basement | Smart TV | Wet Bar
Dining Room | 1st Floor | High Chair
Living Room | 1st Floor | Free WiFi | Central A/C & Heating

Reviews

8.2 out of 10
Very good
5 bedrooms3+ bathroomsSleeps 11260.1 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning
  • Gym

Explore the area

View map
Ossining, NY
  • Place, Ossining Historical Society
    ‪19 min walk‬
  • Place, Carrie Chapman Catt House
    ‪3 min drive‬
  • Place, Van Cortlandt Manor
    ‪6 min drive‬
  • Airport, White Plains, NY (HPN-Westchester County)
    ‪18 min drive‬

Rooms & beds

5 bedrooms (sleeps 11)

Additional Sleeping (Bonus Room)

1 Double Sofa Bed

Additional Sleeping (Game Room)

1 Double Sofa Bed

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

Bedroom 5

2 Single Beds

3 bathrooms, 1 half bathroom

Full Bathroom

Full Bathroom

Full Bathroom

Half Bathroom

Spaces

Deck or patio
Kitchen
Separate dining area
Outdoor play area
Garden

About this property

NYC-Area Escape Near River, Trails & MTA!

Home Gym | Desk | ~4 Mi to Hudson Hills Golf Course

Stay connected to both city energy and river relaxation from this Ossining vacation rental. Spanning 3 levels, this spacious home is 2 miles from the Hudson River and 7 miles from outdoor rec at Croton Gorge Park. Commuting into NYC is simple from Ossining station, putting landmarks like Central Park and Times Square within reach. After a full day out, return to the quiet setting to grill and unwind on the back patio.

-- THE PROPERTY --

INDOOR LIVING
- House-wide Bluetooth speaker system
- Smart TV w/ Disney+, Hulu & Apple TV, DVD player
- Dining room, high chair
- Board games
- Exercise bicycle

OUTDOOR LIVING
- Spacious yard
- Patio w/ charcoal grill/smoker
- Outdoor dining area
- Gas fire pit

ENTERTAINMENT
- Mini bar & foosball table
- Theater system, popcorn & soda machines
- Game area, video games
- Karaoke machine

KITCHEN
- Dishwasher, stove/oven, refrigerator
- Microwave, drip coffee pot, coffee grinder, tea kettle, blender
- Cooking basics, dishware & flatware, kid's dishware, trash bags & paper towels
- Spices

ACCESSIBILITY
- Stairs required for entry, 3-story home
- 1st-floor bedroom & full bathroom

PARKING
- Driveway (2 vehicles)
- Free street parking
- RV/trailer parking allowed on-site
- Garage not for guest use

-- THE LOCATION --

- 1 mile to The Briarcliff Manor
- 2 miles to Louis Engel Waterfront Park: Hudson River
- 3-7 miles to Gedney Park, Croton Point Park, Croton Gorge Park
- 17 miles to Bear Mountain State Park
- 32 miles to Manhattan: One World Observatory, Central Park, Times Square, Rockefeller Center, Lincoln Center for the Performing Arts, Grand Central Station

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- Pet friendly w/ $50 fee (+ fees & taxes, max 2 pets)
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in

ADDITIONAL INFORMATION
- This 3-story home requires stairs for entry. While there is a bedroom and a full bathroom on the 1st floor, stairs are required to access the basement and the 2nd-floor bedrooms and bathroom
- There is a kid's cot available for guest use, but sheets and bedding are not provided for it
- Your safety matters. This property features 3 exterior security cameras: camera 1 is on the front door facing the exterior front entry, camera 2 is above the garage facing the driveway, and camera 3 is on the back facing the backyard/stairs. The cameras do not look into any interior spaces. The cameras record video and sound when activated by motion
- The garage is not available for guest use

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
A maximum of 2 pets are allowed.
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Smoking

Smoking is not permitted

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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the area

Ossining

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 Captain Lawrence Brewing Company and Mohansic Golf Course. Travelling with kids? Consider Westchester County Center and Jacob Burns Film Center Media Arts Lab. Take the opportunity to explore the area for water adventures such as power boating.
View more Holiday homes in OssiningOpens in a new window
Map
Ossining, NY

What's nearby

  • Ossining Historical Society - 19 min walk - 1.7 km
  • Carrie Chapman Catt House - 3 min drive - 2.5 km
  • Van Cortlandt Manor - 6 min drive - 6.0 km
  • Central Park - 51 min drive - 55.7 km
  • Times Square - 61 min drive - 81.7 km

Getting around

  • Ossining Station - 10 min drive
  • White Plains, NY (HPN-Westchester County) - 26 min drive

Restaurants

  • ‪Brothers Fish & Chips - ‬5 min drive
  • ‪105-Ten Bar & Grill - ‬3 min drive
  • ‪Starbucks - ‬3 min drive
  • ‪Asi Es Colombia - ‬3 min drive
  • ‪Ossining Pizzeria and Restaurant - ‬17 min walk

Frequently asked questions

Is NYC-Area Escape Near River, Trails & MTA! pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at NYC-Area Escape Near River, Trails & MTA!?

As of 28 Mar 2026, prices found for a 1-night stay for 2 adults at NYC-Area Escape Near River, Trails & MTA! on 5 July 2026 start from AU$788, 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 NYC-Area Escape Near River, Trails & MTA!?

On-site parking is available at the property.

What time is check-in at NYC-Area Escape Near River, Trails & MTA!?

Check-in begins at 4:00 PM.

What time is check-out at NYC-Area Escape Near River, Trails & MTA!?

Checkout is at 10:00 AM.

Where is NYC-Area Escape Near River, Trails & MTA! located?

This family-friendly Ossining holiday home is within 3 mi (5 km) of Sing Sing Prison Museum, Old Croton Aqueduct State Park and Sing Sing Correctional Facility. Jacob Burns Film Center Media Arts Lab and Jacob Burns Film Center Theater 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 6 out of 15 reviews
Rating 8 - Good. 6 out of 15 reviews
Rating 6 - Okay. 2 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 1 out of 15 reviews

8.8/10

Cleanliness

9.6/10

Check-in

9.0/10

Communication

9.4/10

Location

8.6/10

Listing accuracy

Reviews

Verified

8/10 Good

Joe W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was very communicative.
Stayed 12 nights in Dec 2025
From a partner site

10/10 Excellent

Julia

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.
Verified

8/10 Good

Sabrina S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
From a partner site

10/10 Excellent

Paul

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!
Verified

10/10 Excellent

Pam S.

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

8/10 Good

Joyce S.

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
Verified

10/10 Excellent

Patti K.

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

Comfortable Home

This was our Christmas gathering place for family from 4 states. Beautiful home and location.
Stayed 4 nights in Dec 2024
Verified

10/10 Excellent

David W.

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

Family funeral

Family funeral brought us to the area. House was excellent for us
Stayed 3 nights in Nov 2024
Verified

10/10 Excellent

Samantha C.

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

Perfect house!

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!
Stayed 3 nights in Oct 2024
Verified

6/10 Okay

Heidi E.

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

Nice visit

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
Verified

8/10 Good

Matthew S.

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

Nice house

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
Stayed 4 nights in Sep 2024
Verified

8/10 Good

Abby K.

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

Great place for group accommodations

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.
Stayed 4 nights in Oct 2024
Verified

6/10 Okay

Madeleine M.

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

Amenities

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.
Stayed 4 nights in Jul 2024
Verified

2/10 Terrible

Vanessa M.

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

Worse VRBO Ever

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
Verified

8/10 Good

Tanya C.

Liked: Cleanliness, check-in, communication
Stayed 7 nights in Apr 2025

About the host

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