Holiday Homes in Ossining

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 July - 12 July
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Ossining holiday homes

Outdoor banquet area

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 AU$1,861
includes taxes & fees
20 May - 21 May
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Villa

Westchester Summer Pool Pet Friendly Events Games

Westchester Summer Pool Pet Friendly Events Games
2.0 star property
Ossining
The price is AU$2,326
includes taxes & fees
18 May - 19 May
Westchester Summer Pool Pet Friendly Events Games
Property grounds

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 AU$493
includes taxes & fees
25 May - 26 May
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

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 AU$441
includes taxes & fees
20 May - 21 May
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Exterior

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is AU$331
includes taxes & fees
14 May - 15 May
Luxury home near West Point
TV, fireplace

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 AU$536
includes taxes & fees
21 May - 22 May
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Terrace/patio

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 AU$189
includes taxes & fees
17 May - 18 May
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Terrace/patio

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

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AU$583
includes taxes & fees
18 May - 19 May
House on the Babbling Brook- Quiet 2BR + King Bed!
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is AU$441
includes taxes & fees
3 June - 4 June
Luxury House Near West Point
Interior

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.2 out of 10, Wonderful, (24 reviews)
"House was amazing, with a wonderful view. Hosts were responsive and helpful. Will need to come back in summer!"
United States
Scott H.
The price is AU$1,373
includes taxes & fees
14 May - 15 May
Waterview House Walking Distance from Cove Beach
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (6 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is AU$575
includes taxes & fees
27 May - 28 May
Fabulous 3bdrm Home w/parking!
Outdoor dining

Stamford : The Comfy Cove Hideout

Stamford : The Comfy Cove Hideout
Cove - East Side - Shippan
The price is AU$389
includes taxes & fees
28 May - 29 May
Stamford : The Comfy Cove Hideout
Fridge, microwave, oven, stovetop

Modern 1BR Apt / Free Parking / Near NYC

Modern 1BR Apt / Free Parking / Near NYC
White Plains
10.0 out of 10, Exceptional, (1 review)
"Very clean, fully stocked with all you need to cook full meals. If coming back to the area, 10/10 would stay again."
United States
Mike J.
The price is AU$463
includes taxes & fees
20 May - 21 May
Modern 1BR Apt / Free Parking / Near NYC
Property grounds

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, (7 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 AU$575
includes taxes & fees
17 May - 18 May
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is AU$621
includes taxes & fees
31 May - 1 June
Contemporary Cozy Cottage
Luxury Apartment | Living area

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 AU$826
includes taxes & fees
15 May - 16 May
Luxury 3 BR Near NYC with Easy Parking
Interior

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 AU$597
includes taxes & fees
27 May - 28 May
Lovely 3BR Home with parking-Walk to WP Gate!
Smart TV

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

Spacious 3BR Home / Free Parking / Perfect for Families & Groups
White Plains
The price is AU$938
includes taxes & fees
20 May - 21 May
Spacious 3BR Home / Free Parking / Perfect for Families & Groups
In-room safe, iron/ironing board, travel cot, free WiFi

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 AU$958
includes taxes & fees
28 May - 29 May
Perfect Family Getaway / 5BR Home / 6 Queen Beds / Free Parking
In-room safe, iron/ironing board, travel cot, free WiFi

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 AU$969
includes taxes & fees
14 May - 15 May
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
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

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

8/10 Good
"Breakfast menus doesn’t have much varieties, very simple. Pool need maintenance. "
Jenny 1-night trip
Posted 5 hours ago
Baymont by Wyndham White Plains - Elmsford

Find out more about Ossining

Ossining Holiday Homes information

Number of reviews
163
Accommodation
352 Holiday Homes
Lowest Price
AU$189
Highest Price
AU$2,326