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Holiday Homes in Ossining

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Ossining

Our top choices for Ossining holiday homes

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (87)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC
Pool

⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC

4.0 star property
10.0 out of 10, Exceptional, (7)
"This place was perfect for our family members - 7 adults. Everyone had their own bed and there were plenty of pillows and towels for all. It was quite clean and decorated nicely. The kitchen was well stocked with anything we might need and more. Thank you to the excellent hosts!"
⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Fridge, microwave, oven, stovetop

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (36)
"Short trip. great place to stay . Very cozy . Family loved it "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Bright Cornwall-On-Hudson Vacation Rental!
Fridge, microwave, stovetop, dishwasher

Bright Cornwall-On-Hudson Vacation Rental!

10.0 out of 10, Exceptional, (22)
"Property was perfect for our needs."
Bright Cornwall-On-Hudson Vacation Rental!
Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10.0 out of 10, Exceptional, (2)
"Lovely little home in Stamford."
The price is AU$551
includes taxes & fees
1 Sept - 2 Sept
Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Modern 4BD/3BA w/Parking & deck & 29 min>NYC
Outdoor dining

Modern 4BD/3BA w/Parking & deck & 29 min>NYC

9.8 out of 10, Exceptional, (17)
"The house was very clean and the check-in process was smooth. Host was very responsive. Overall we loved our stay and would definitely book again next time we're in the area!"
Modern 4BD/3BA w/Parking & deck & 29 min>NYC
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Fridge, microwave, stovetop, dishwasher

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

10.0 out of 10, Exceptional, (36)
"Perfect for our family’s visit to West Point. Great location "
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Charming Highland Falls Home < 2 Mi to West Point!
Exterior

Charming Highland Falls Home < 2 Mi to West Point!

10.0 out of 10, Exceptional, (9)
"Wonderful front porch "
Charming Highland Falls Home < 2 Mi to West Point!
Spacious 4-bedroom house in charming Rye with AC
Miscellaneous

Spacious 4-bedroom house in charming Rye with AC

The price is AU$716
includes taxes & fees
1 Sept - 2 Sept
Spacious 4-bedroom house in charming Rye with AC
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Property grounds

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
The price is AU$505
includes taxes & fees
8 Sept - 9 Sept
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Modern Luxury Home w GameRoom & Parking
House | Living area

Modern Luxury Home w GameRoom & Parking

3.0 star property
7.0 out of 10, Good, (4)
"Put down a deposit with the understanding that the deposit would be back in my account within 24 hours. Messaged them several times and I have not gotten any response nor have I gotten my money back and it has been days now with no response. Apartment was filthy, beds were used and not cleaned, bunch of appliances didn’t work, found a towel with stains potentially from bodily fluids.DO NOT BOOK WITH THEM THEY ARE SCAMMERS. Charged a cleaning fee on top of this for an apartment that wasn’t even...
The price is AU$1,089
includes taxes & fees
25 Aug - 26 Aug
Modern Luxury Home w GameRoom & Parking
Cozy 2 Bedroom, Near NYC, Easy Parking
Outdoor dining

Cozy 2 Bedroom, Near NYC, Easy Parking

10.0 out of 10, Exceptional, (2)
"Owners very responsive. I didn’t see message with check-out process (garbage etc) until after I left so I would suggest including with listing or providing upon check-in. Place was very clean! Easy on street parking. Only two towels though, for two females for two days. Not a huge deal but would have liked one or two more. "
Cozy 2 Bedroom, Near NYC, Easy Parking
Serene Hudson Valley Escape w/ Pool & Grill
Fridge, microwave, stovetop, dishwasher

Serene Hudson Valley Escape w/ Pool & Grill

10.0 out of 10, Exceptional, (3)
"Beautiful home and great host!"
Serene Hudson Valley Escape w/ Pool & Grill
Mid-Century Seclusion: An Architectural Marvel w/ Hot Tub
TV, fireplace, offices

Mid-Century Seclusion: An Architectural Marvel w/ Hot Tub

10.0 out of 10, Exceptional, (3)
"Lovely home for a get away. "
Mid-Century Seclusion: An Architectural Marvel w/ Hot Tub
Home: 2 Mi to Thayer Gate at U.S. Military Academy
Fridge, microwave, stovetop, dishwasher

Home: 2 Mi to Thayer Gate at U.S. Military Academy

10.0 out of 10, Exceptional, (2)
"Your home was amazing! My family and I enjoyed every minute! "
Home: 2 Mi to Thayer Gate at U.S. Military Academy
Charming 3-bedroom house.
Property grounds

Charming 3-bedroom house.

2.0 star property
10.0 out of 10, Exceptional, (10)
"The property was very clean and nicely furnished. A nice quiet spot."
Charming 3-bedroom house.
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
Fridge, microwave, oven, stovetop

Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

2.0 star property
9.8 out of 10, Exceptional, (12)
"Clean and spacious apartment in a quiet neighborhood."
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
Harriman Outdoor Center - White Oak Cabin
Property grounds

Harriman Outdoor Center - White Oak Cabin

The price is AU$382
includes taxes & fees
7 Sept - 8 Sept
Harriman Outdoor Center - White Oak Cabin
Lovely 3BR Home with parking-Walk to WP Gate!
Interior

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

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is AU$517
includes taxes & fees
10 Sept - 11 Sept
Lovely 3BR Home with parking-Walk to WP Gate!
New Jersey home, close to NY City Fun!
Dining

New Jersey home, close to NY City Fun!

8.8 out of 10, Excellent, (6)
"My family and I stayed at Gloria's place for a few days to attend the funeral of our grandmother. The house was perfect for all of our needs and Gloria made us feel at home. "
New Jersey home, close to NY City Fun!
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

Amsterdam Hotel

Amsterdam Hotel

10/10 Excellent
"The desk staff were very kind and helpful. The beds were extremely comfortable!"
DARLENE 1-night trip
Posted 19 hours ago
Amsterdam Hotel