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Compare 248 Vacation Homes in Ossining with updated reviews, rates, and availability.

Lower Lvl Private 2BR/1BA Family/Pet Friendly
Exterior
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (113)
"Beautiful neighborhood. Absolutely clean. Apartment was laid out kind of strange. The stairs to go down into the apartment were a little tough. It was very dark walking the path and then the stairs are very narrow. Other than that, the place was perfect for what we needed. A clean house, a place to shower and sleep. I would stay again if ever in the area."
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Interior
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (74)
"This place was a great place for us to stay on our vacation. Secluded outside of the city, and a short drive down a gravel road, it really feels that you're lost in the woods, but in a good way. If you're up to visit the Gunks, Angry Orchard, the Hudson river, love the beauty of the outdoors, and have other family or friends to visit in the area, definitely consider this home. Host was very responsive and had everything ready for us."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Miscellaneous
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
10.0 out of 10, Exceptional, (10)
"We wanted to spend a night in cold spring after a hike but couldn't find anything last minute in the area, so ended up booking this lovely property a little bit away. At first I was skeptical because of the drive (about 40-45 mins if I remember correctly). But I'm so glad we ended up doing this. Cold spring was just so busy and crowded, we couldn't even get lunch easily. The property is located right across a lake and is on a rather quite street. We reached the property around 5pm just in time...
The price is AED 1,502
AED 2,917 total
includes taxes & fees
12 Nov - 13 Nov
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Living room
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
9.0 out of 10, Wonderful, (15)
"The floor is slippery, including the stairs, and we had 3 falls because of it (4 middleaged, ambulatory people). Otherwise, in a good neighborhood, clean, very spacious and well stocked with a large kitchen."
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Garrison Vacation Rental | 2BR | 2.5BA | 1,700 Sq Ft | 1 Step to Enter
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
10.0 out of 10, Exceptional, (22)
"House was beautifully furnished with lovely touches of art work and lovely succulent plants. The hot tub was a great touch, and we enjoyed it every morning. The children loved exploring the property. Thank you!"
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
UPDATED BLUE BARN CARRIAGE HOUSE CIRCA1887
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
9.8 out of 10, Exceptional, (46)
"Wonderful property in a very quiet neighborhood 20 minutes from Metlife Stadium. Lisa provided lots of very helpful information. We used the hot tub, steam room and sauna. The decor was very nice! We would definitely stay there again as it is very close to Metlife and also very close to NYC."
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
Modern And Quiet Getaway
Room
Modern And Quiet Getaway
9.8 out of 10, Exceptional, (22)
"We stayed for several days because the price was 1/4 the price of staying in the city. The apartment was clean and private. Parking was free and we ran in the neighborhood each morning. Everyone we met was very nice. "
Modern And Quiet Getaway
Perfect for families and large groups
Come on in -- the water's fine! Who else is ready to take a dip and soak up some sun?
Perfect for families and large groups
9.4 out of 10, Exceptional, (9)
"I rented this property for my co-workers who were here for a retreat at my home in the area, and at the local community center. This home had everything we needed, and the host was easy to communicate with. We will definitely consider using this property again for future guests coming for work and family gatherings."
Perfect for families and large groups
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury
Private kitchen
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury
9.2 out of 10, Wonderful, (7)
"Super well-appointed house with everything we needed for our stay. Hosts were easy to communicate with and responded very quickly."
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury
Contemporary Cozy Cottage
Exterior
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (12)
"An absolutely charming cottage with beautiful decor and peaceful neighborhood… close to shopping and resturants…. Also conveniece ti train station if traveling into Manhattan… A great perfect place to stay if visiting the area. "
The price is AED 918
AED 1,385 total
includes taxes & fees
10 Nov - 11 Nov
Contemporary Cozy Cottage
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
The front door leads to a porch, patio, and small yard.
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
9.0 out of 10, Wonderful, (23)
"The home was very clean and had everything we needed - snacks games and a cute patio. The internet was iffy and never worked to stream on the bedroom tv. They came and checked it , but it didn’t improve. The host was very responsive and offered to ship an item our daughter left. We would rent again. "
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail
Exterior
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail
10.0 out of 10, Exceptional, (34)
"Our stay at Gersende's property was delightful. We had seven friends together for a wedding and this house and property served as a much appreciated comfortable and peaceful retreat. The pool was lovely, the kitchen was well-stocked and functional and the homes quirks and charm grew on us a little more each day. We walked to GrayBarns Mercantile every morning for coffee and it was a quick drive from the grocery as well as the PJ Glass House. Gersende was kind, easy to reach and incredibly...
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail
Peaceful 5 Bed NY Villa - 30 min from NYC
Living area
Peaceful 5 Bed NY Villa - 30 min from NYC
9.0 out of 10, Wonderful, (6)
"Spacious and cozy home. Would love to come back in the summer to enjoy the yard. Perfect for families."
Peaceful 5 Bed NY Villa - 30 min from NYC
Stylish Beach Home near Stamford Downtown/Beach
Cozy backyard with fire pit and BBQ grill
Stylish Beach Home near Stamford Downtown/Beach
10.0 out of 10, Exceptional, (19)
"Our group of adults and 5 teenage boys loved this home. It was clean and well equipped for everything we needed for our stay. The beds and furniture were extremely comfortable. There is so much to do in the area, as well as at the home. The beach was a very short distance away and beautiful. We loved the game table and the fire pit at the home. Don’t hesitate to book - you won’t regret it!"
The price is AED 1,759
AED 3,469 total
includes taxes & fees
12 Nov - 13 Nov
Stylish Beach Home near Stamford Downtown/Beach
Amazing 3BR/3BA! Croton on Hudson!
41
Amazing 3BR/3BA! Croton on Hudson!
7.0 out of 10, Good, (2)
"We found the house pleasant and centrally located"
Amazing 3BR/3BA! Croton on Hudson!
Waterfront Lake House. Near NYC and hiking trials. Complimentary kayaks provided
Exterior
Waterfront Lake House. Near NYC and hiking trials. Complimentary kayaks provided
2.0 star property
10.0 out of 10, Exceptional, (2)
"This beautiful lake house was just as pictured! Great location with waterfront access and fun water crafts provided by owner. Brian was a pleasure to work with and answered all my questions immediately, also gave restaurant recommendations. We will be staying again!"
Waterfront Lake House. Near NYC and hiking trials. Complimentary kayaks provided
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
Private kitchen
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
2.0 star property
8.0 out of 10, Very Good, (2)
"The apartment is on the second floor on a dead end st. It is very clean and spacious with new appliances. Host are lovely couple. I only wish that the second bedroom had a full length mirror or any mirror. The master bedroom has 2 and the other had none. Had to keep going into the other room to use mirror. Had trouble using the TV, finally I had to mirror cast/share screen from my cell phone to the tv in order to watch anything. Overall it was a lovely and will go again. "
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
Luxury 3Bed Private Apartment Near Manhattan
Living area
Luxury 3Bed Private Apartment Near Manhattan
9.2 out of 10, Wonderful, (9)
"everything was very good but street parking not sasy"
The price is AED 1,084
AED 1,840 total
includes taxes & fees
6 Nov - 7 Nov
Luxury 3Bed Private Apartment Near Manhattan
Renovated 1850's Cottage on Storm King Mountain
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (14)
"Great place!"
Renovated 1850's Cottage on Storm King Mountain
2 mini-bedrooms apartment with antique bathtub.
Private kitchen
2 mini-bedrooms apartment with antique bathtub.
10.0 out of 10, Exceptional, (18)
"Conveniently located to small downtown area & train into NYC. "
2 mini-bedrooms apartment with antique bathtub.
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.
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Other property types in Ossining

Stamford Suites
Property amenity
Stamford Suites
2.5 star property
6.8 out of 10, (758)
"Had a good time pricing is on the money for that location. They had problems with their card system at first but the front desk worker was trying his best and he make it relaxing "
The price is AED 528
AED 591 total
includes taxes & fees
11 Nov - 12 Nov
Stamford Suites
Waterfront Retreat Center for Health & Wellness
Exterior
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, (53)
"Old house, beautiful location on the Sound in New Rochelle, NY. The owners are a not-for-profit who are kind and helpful throughout. House is old and has lovely period touches. House well stocked with linen and towels; kitchen had all items needed. Suggestions: 1. Some of the bathrooms do not have latches or locks. Needs to be fixed. 2. Some sinks slow to drain. 3. A dishwasher would be a great addition. 4. Uber found it difficult to find the house. They either overshot it or fell short of...
Waterfront Retreat Center for Health & Wellness
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is AED 617
AED 911 total
includes taxes & fees
11 Nov - 12 Nov
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.