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Our top choices for Ossining holiday homes

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
9.2 out of 10, Wonderful, (7 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is HK$6,265
HK$10,624 total
includes taxes & fees
20 May - 21 May
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Westchester Summer Pool Pet Friendly Events Games

Westchester Summer Pool Pet Friendly Events Games
2.0 star property
Ossining
The price is HK$6,071
HK$10,672 total
includes taxes & fees
20 May - 21 May
Westchester Summer Pool Pet Friendly Events Games

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, (34 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is HK$1,339
HK$2,495 total
includes taxes & fees
1 Jun - 2 Jun
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
The price is HK$3,150
HK$4,690 total
includes taxes & fees
23 May - 24 May
Luxury 3 BR Near NYC with Easy Parking

The Victorian Blue 25min to NYC

The Victorian Blue 25min to NYC
North Side
9.8 out of 10, Exceptional, (8 reviews)
"The accommodations were fantastic, with spacious rooms, modern amenities, and breathtaking views. Additionally, the host was incredibly accommodating, ensuring that every aspect of my stay was comfortable and enjoyable. I highly recommend this property to anyone looking for a perfect getaway with a gracious host!"
United States
Honna C.
The price is HK$4,962
HK$9,072 total
includes taxes & fees
20 May - 21 May
The Victorian Blue 25min to NYC

Spacious 3BR Home / Free Parking / Perfect for Families & Groups

Spacious 3BR Home / Free Parking / Perfect for Families & Groups
White Plains
The price is HK$2,960
HK$5,365 total
includes taxes & fees
20 May - 21 May
Spacious 3BR Home / Free Parking / Perfect for Families & Groups

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
Bryn Mawr
The price is HK$2,960
HK$5,560 total
includes taxes & fees
26 May - 27 May
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly

Perfect Family Getaway / 5BR Home / 6 Queen Beds / Free Parking

Perfect Family Getaway / 5BR Home / 6 Queen Beds / Free Parking
Bryn Mawr
The price is HK$2,960
HK$5,560 total
includes taxes & fees
20 May - 21 May
Perfect Family Getaway / 5BR Home / 6 Queen Beds / Free Parking

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$1,586
HK$3,085 total
includes taxes & fees
21 May - 22 May
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (13 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,276
HK$2,634 total
includes taxes & fees
25 May - 26 May
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Luxury NYC Retreat with Free Parking

Luxury NYC Retreat with Free Parking
White Plains
8.0 out of 10, Very good, (1 review)
"Everything was perfect ! "
Canada
Eric
The price is HK$3,289
HK$5,786 total
includes taxes & fees
31 May - 1 Jun
Luxury NYC Retreat with Free Parking

Cheerful Home in Yonkers NY

Cheerful Home in Yonkers NY
Lincoln Park
7.6 out of 10, Good, (4 reviews)
"Nice neighborhood,open concept.Hreat space for my entire family.Kitchen big and spacious. Beds are huge. Definitely will stay here again."
United States
Tanya J.
The price is HK$1,958
HK$4,573 total
includes taxes & fees
20 May - 21 May
Cheerful Home in Yonkers NY

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 HK$740
HK$1,056 total
includes taxes & fees
24 May - 25 May
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (8 reviews)
"We had a great time staying here. It was very clean and the view was amazing. Wanted to meet up with some family and it was perfect for relaxing and catching up. Host accommodated our early check in request and was available during our stay when we had minor questions. Overall, it was wonderful."
United States
Joe K.
The price is HK$1,817
HK$3,515 total
includes taxes & fees
31 May - 1 Jun
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (1 review)
The price is HK$3,987
HK$5,627 total
includes taxes & fees
20 May - 21 May
3BR Prime Luxury near NYC w Arcade Room

Spacious 2 Bedroom Home / Parking Included / Near NYC

Spacious 2 Bedroom Home / Parking Included / Near NYC
Bryn Mawr
The price is HK$2,114
HK$4,407 total
includes taxes & fees
25 May - 26 May
Spacious 2 Bedroom Home / Parking Included / Near NYC

Modern Home off I-95 Perfect for Families & Business Stay with Ample Parking

Modern Home off I-95 Perfect for Families & Business Stay with Ample Parking
Cove - East Side - Shippan
8.0 out of 10, Very good, (6 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is HK$1,579
HK$3,609 total
includes taxes & fees
20 May - 21 May
Modern Home off I-95 Perfect for Families & Business Stay with Ample Parking

Walkable Townhouse with Garage & Yard, 45 min to NYC!

Walkable Townhouse with Garage & Yard, 45 min to NYC!
West Side
9.4 out of 10, Exceptional, (6 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 HK$3,265
HK$5,760 total
includes taxes & fees
24 May - 25 May
Walkable Townhouse with Garage & Yard, 45 min to NYC!

Prime NY Luxury Getaway King Bed + Easy Parking

Prime NY Luxury Getaway King Bed + Easy Parking
Southeast Yonkers
The price is HK$2,960
HK$5,495 total
includes taxes & fees
20 May - 21 May
Prime NY Luxury Getaway King Bed + Easy Parking

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Excellent home, met all expectations, and attentive staff"
United States
Steve G.
The price is HK$3,618
HK$7,734 total
includes taxes & fees
20 May - 21 May
New Beach Home near Stamford Downtown/Shippan
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

Find out more about Ossining

Ossining Vacation Homes information

Number of reviews
95
Accommodation
354 Vacation Homes
Lowest Price
HK$2,495
Highest Price
HK$10,672

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