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Compare 306 Vacation Homes in Ossining with updated reviews, rates, and availability.

Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (105)
"This is a fantastic property and host"
Lower Lvl Private 2BR/1BA Family/Pet Friendly
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
10.0 out of 10, Exceptional, (5)
"The property was as advertised with every amenity imaginable. A good option for doing NYC"
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (63)
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
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Modern Colonial House
10.0 out of 10, Exceptional, (11)
"Stayed with my family for 6 days and it was perfection! This was our first time traveling with my 6 month old and I was a bit anxious but the place was beautiful, clean, spacious, and well-appointed. Carmel brought over a high chair for us, and some crib sheets, which was very thoughtful. We initially debated staying in the city but this was by far the better choice! You can’t get anything like this in the 5 boroughs (and this was literally a hop, skip and jump from the Bronx anyway). Would...
Modern Colonial House
Close to a train, White Plains to NYC.
10.0 out of 10, Exceptional, (2)
"The residence was very nice and looked exactly like the photos. Would recommend to others who are looking for a get away. Thanks again for allowing me to book your location"
Close to a train, White Plains to NYC.
The Woodbury Cottage
10.0 out of 10, Exceptional, (1)
"We really enjoyed relaxing on the front porch after a busy day out. Beds were very comfortable. So nice to be able to sit around and visit, instead being in a hotel, sitting on beds. We did miss having a microwave to use. Very nice and affordable."
The Woodbury Cottage
Aspen In Airmont NY
10.0 out of 10, Exceptional, (2)
"This property is set on a private wooded lot with stream and fantastic outdoor amenities. Beautiful decks, hot tub, large fire pit, trampoline, zipline, swings, hammocks, plenty of parking and outdoor refrigerators. We saw wildlife including birds, turtles and deer. It is well-equipped and set up for large gatherings. Extra bedding and inflatable mattresses for extra sleeping capabilities. Excellent for families. Conveniently close to grocery stores and restaurants. 40 minute drive up to USMA."
The price is SAR 3,377
SAR 5,492 total
includes taxes & fees
20 Jun - 21 Jun
20 Jum. II - 21 Jum. II
Aspen In Airmont NY
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, (50)
"We stayed at the New Dawn for a Memorial Service. The setting on the water was so peaceful and private, yet easy access for those of us traveling by public transportation from Manhattan and La Guardia airport. We had chairs lined up facing the water for a Celebration of Life Ceremony. The whole downstairs layout was just wonderful with indoor and outdoor areas for people to gather, sharing memories and grief. Food platters from Costco were easily arranged and the weather was perfect. It was so...
Waterfront Retreat Center for Health & Wellness
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (38)
"My husband and I greatly enjoyed our stay! We mentioned that we were traveling for our honeymoon and upon our arrival, the host had left a bottle of wine and some little decorations on the dining room table to celebrate our marriage! It was so thoughtful and sweet!! The Vrbo itself was cozy and tidy. We enjoyed cooking in the kitchen and listening to the music of Motown on the cd player. Our host was prompt to respond to messages and answered all questions clearly. We loved staying close to so...
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
10.0 out of 10, Exceptional, (22)
"My family and I had a wonderful weekend at the property. It rained most of the time, but we made the best of it. It was all over too fast. It's a nice, relaxing property."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Luxury 3Bed Private Apartment Near Manhattan
10.0 out of 10, Exceptional, (5)
"Great place to spend the night, amazing place to stay with family and friends! "
The price is SAR 1,163
SAR 1,951 total
includes taxes & fees
24 Jun - 25 Jun
24 Jum. II - 25 Jum. II
Luxury 3Bed Private Apartment Near Manhattan
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Private room in a single family house near Peekskill
9.8 out of 10, Exceptional, (13)
"My wife and I enjoyed our stay. Property owner was very responsive to questions. Home was very clean and inviting. We loved the cats!"
The price is SAR 236
SAR 536 total
includes taxes & fees
26 Jun - 27 Jun
26 Jum. II - 27 Jum. II
Private room in a single family house near Peekskill
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury
9.6 out of 10, Exceptional, (5)
"We spent a long weekend in New Rochelle for a girls weekend. The house was very clean and had everything we needed it to have. beds were comfortable, the outdoor patio with gas fire pit was perfect for your relaxing nights. The host, Hamza was courteous and quick to respond to our queries. Would recommend !"
The price is SAR 1,553
SAR 2,466 total
includes taxes & fees
20 Jul - 21 Jul
20 Raj. - 21 Raj.
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (4)
"Everything was great and as advertised. The pizza place down the hill hit the spot when traveling in a bit later than expected."
The price is SAR 938
SAR 1,411 total
includes taxes & fees
24 Jun - 25 Jun
24 Jum. II - 25 Jum. II
Contemporary Cozy Cottage
Charming Mamaroneck Home ~ 22 Mi to Manhattan
7.0 out of 10, Good, (6)
"The house was exactly as described close to trains and restaurants, was clean with all amenities. We would rent again."
Charming Mamaroneck Home ~ 22 Mi to Manhattan
Bright Cornwall-On-Hudson Vacation Rental!
10.0 out of 10, Exceptional, (5)
"We enjoyed 4 nights at this lovely, beautifully renovated home. It was the perfect size for the 6 of us and we took advantage of the back patio for grilling and dining. The decor is lovely and the kitchen very well equipped. We had everything we needed and more."
Bright Cornwall-On-Hudson Vacation Rental!
Modern, Magical Woodsy Escape 1 Hour From NYC
10.0 out of 10, Exceptional, (11)
"Everything about this place was perfect and allowed our family to grieve our loss in comfort and zen"
Modern, Magical Woodsy Escape 1 Hour From NYC
Updated Home w/ Patio Half Mile to West Point
10.0 out of 10, Exceptional, (19)
"We were visiting West Point Academy and wanted a place to stay for our family of five. Perfect location and just what we needed for a couple of nights. Would stay again if we are back in the area!"
Updated Home w/ Patio Half Mile to West Point
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See all available properties in Ossining
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Ossining

Stamford Suites
2.5 star property
6.8 out of 10, (726)
"We loved all the dining options that were just a few minutes walk from the hotel. The hotel is outdated but it was very clean and the suites were spacious. The staff was friendly and helpful. "
The price is SAR 686
SAR 768 total
includes taxes & fees
3 Jul - 4 Jul
3 Raj. - 4 Raj.
Stamford Suites
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, (50)
"We stayed at the New Dawn for a Memorial Service. The setting on the water was so peaceful and private, yet easy access for those of us traveling by public transportation from Manhattan and La Guardia airport. We had chairs lined up facing the water for a Celebration of Life Ceremony. The whole downstairs layout was just wonderful with indoor and outdoor areas for people to gather, sharing memories and grief. Food platters from Costco were easily arranged and the weather was perfect. It was so...
Waterfront Retreat Center for Health & Wellness
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is SAR 807
SAR 1,129 total
includes taxes & fees
24 Jun - 25 Jun
24 Jum. II - 25 Jum. II
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Recent reviews of Ossining hotels
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