A wooden boardwalk winding through a forest with autumn foliage.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Ossining holiday homes

A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

1. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
Ossining
8.2 out of 10, Very good, (19 reviews)
"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!"
United States
Justeen P.
Snow Days & City Escapes: Spacious Ossining Home
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is £784
includes taxes & fees
3 Nov - 4 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is £695
includes taxes & fees
3 Nov - 4 Nov
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

4. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (41 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is £320
includes taxes & fees
20 Oct - 21 Oct
Contemporary Cozy Cottage
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

5. Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is £104
includes taxes & fees
20 Oct - 21 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A room with two beds, white curtains, a ceiling light, and a window with a view.

6. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
2.0 out of 10, (1 review)
"This guy is a scammer, an hour before my checkin they finally sent me the "location" and claimed they needed more time to clean the property. Then at 5 pm and hour after they claimed their was a gas leak and I couldn't stay there. Only thing is the address they sent me wasn't real and I am convinced this listing is fake in and used to trick people into staying at their actual property in yonkers. DO NOT RENT FROM THEM!"
United States
Ethan G.
The price is £627
includes taxes & fees
20 Oct - 21 Oct
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

7. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (14 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is £309
includes taxes & fees
20 Oct - 21 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

8. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is £299
includes taxes & fees
17 Nov - 18 Nov
Fabulous 3bdrm Home w/parking!
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

9. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (45 reviews)
"Nice stay"
United States
Christopher J.
The price is £281
includes taxes & fees
18 Nov - 19 Nov
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

10. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay at the lake house. The home is beautiful inside and out, and there is every amenity you could think of, from cooking and cleaning supplies to extra towels and blankets. The view of the lake is stunning and we enjoyed the peace and quiet of the little community. Linh is an excellent host and helped answer all of our questions. We will definitely be back!"
United States
Angel R.
The price is £491
includes taxes & fees
22 Oct - 23 Oct
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

11. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
The price is £373
includes taxes & fees
2 Nov - 3 Nov
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

12. Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC

Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
White Plains
2.0 out of 10, (1 review)
"An hour before check-in we were called by the property manager, after four days of messaging them through the app without response, to advise us that the property had an alleged water pipe burst and was unavailable, then attempted to upcharge us for alternate accommodations. An alternate place to stay was finally provided at no additional charge but much smaller than what had been booked. Given the absence of communication for four days and then a sudden incident the day of check-in - the day...
United States
James D.
The price is £1,032
includes taxes & fees
20 Oct - 21 Oct
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
An outdoor patio with a fire pit, green chairs, and a table.

13. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
10.0 out of 10, Exceptional, (12 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is £269
includes taxes & fees
27 Oct - 28 Oct
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A room with a wooden door, a small table with a vase, and a chair.

14. Spacious 3b/3b Mediterranean in White Plains

Spacious 3b/3b Mediterranean in White Plains
White Plains
9.4 out of 10, Exceptional, (18 reviews)
"This was a wonderful property. It was very charming and had everything we could need. Great neighborhood, lots of room very comfortable. We would definitely stay there again. Great host response!"
United States
Nancy K.
The price is £657
includes taxes & fees
22 Oct - 23 Oct
Spacious 3b/3b Mediterranean in White Plains
A room with a wooden floor, a white door with a number, and a window with blinds.

15. Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is £291
includes taxes & fees
17 Nov - 18 Nov
Lovely 3BR Home with parking-Walk to WP Gate!
A modern kitchen with stainless steel appliances, a marble countertop, and a dining area with white chairs.

16. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is £272
includes taxes & fees
20 Oct - 21 Oct
Hudson Valley/West Point Retreat w/ parking!
A deck with Adirondack chairs, a fire pit, and a grill.

17. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Cornwall
10.0 out of 10, Exceptional, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is £335
includes taxes & fees
3 Nov - 4 Nov
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A bedroom with a bed, bedside tables, a mirror, a wardrobe, and a painting on the wall.

18. Gem by the water+ firepit and all fenced backyard

Gem by the water+ firepit and all fenced backyard
Waterside
10.0 out of 10, Exceptional, (21 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is £345
includes taxes & fees
20 Oct - 21 Oct
Gem by the water+ firepit and all fenced backyard
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

19. Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
Greenwich
10.0 out of 10, Exceptional, (2 reviews)
"Great location on the lake which the kids loved. The hosts were very friendly and easy to communicate with. The addition of the outdoor grill was a big plus and we enjoyed many afternoons out on the deck. We would stay again."
United States
Nathan R.
The price is £1,825
includes taxes & fees
20 Oct - 21 Oct
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A modern living room with a white sofa, a glass coffee table, and a piano.

20. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.2 out of 10, Wonderful, (9 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is £491
includes taxes & fees
27 Oct - 28 Oct
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
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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Top Ossining Hotel Reviews

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"⭐⭐⭐⭐⭐ Exceptional Hospitality — The People Make This Place Special! I've stayed at many hotels, but my experience at the Hyatt Regency Greenwich genuinely stood out, and I couldn't leave without recognizing the incredible people who made it so memorable. From the moment I arrived, I felt welcomed. Not just greeted, but genuinely welcomed. There's a difference, and the team here understands it beautifully. Saul, our server, was wonderful. Riley at the bar, Julio in the restaurant, Danielle, the manager, and Lewin, the bellhop, all contributed to such a positive experience. I also want to recognize German who I spoke with briefly who has been working there almost as long as I have been alive! Talk about Retention. Every interaction reflected warmth, friendliness, and genuine hospitality. What impressed me most was the consistency. It wasn't one exceptional employee carrying the experience. It was the culture of hospitality demonstrated by the people I encountered throughout the property. As a business owner who hosts events, transformative experiences, and retreats, I pay close attention to how people are treated in the spaces I consider bringing my clients into. My experience here was so positive that the Hyatt Regency Greenwich is now top of mind as a potential location for future events and retreats. That speaks volumes. Beautiful spaces are wonderful, but it's the people who create an experience worth remembering. And this team absolutely delivered."
Hayley 2-night trip
Posted 12 hours ago
Hyatt Regency Greenwich

Find out more about Ossining

Ossining Holiday Homes information

Number of reviews
256
Accommodation
253 Holiday Homes
Lowest Price
£104
Highest Price
£1,825