Search Vacation Homes in Ossining

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Ossining vacation 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 AED 1,638
AED 3,390 total
includes taxes & fees
21 Apr - 22 Apr
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 AED 1,795
AED 3,694 total
includes taxes & fees
13 Apr - 14 Apr
Westchester Summer Pool Pet Friendly Events Games

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
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is AED 655
AED 1,322 total
includes taxes & fees
17 Apr - 18 Apr
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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
9.6 out of 10, Exceptional, (30 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AED 545
AED 1,075 total
includes taxes & fees
14 Apr - 15 Apr
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (32 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is AED 826
AED 1,533 total
includes taxes & fees
13 Apr - 14 Apr
Contemporary Cozy Cottage

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)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is AED 744
AED 1,447 total
includes taxes & fees
13 Apr - 14 Apr
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

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
8.2 out of 10, Very Good, (18 reviews)
"Great location"
United States
Jordan S.
The price is AED 347
AED 495 total
includes taxes & fees
12 Apr - 13 Apr
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Luxury NY Home with Free Parking

Luxury NY Home with Free Parking
4.0 star property
White Plains
8.0 out of 10, Very Good, (1 review)
"Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine. "
United States
Safiya
The price is AED 876
AED 1,549 total
includes taxes & fees
12 Apr - 13 Apr
Luxury NY Home with Free Parking

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 AED 500
AED 1,478 total
includes taxes & fees
13 Apr - 14 Apr
House on the Babbling Brook- Quiet 2BR + King Bed!

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is AED 735
AED 1,167 total
includes taxes & fees
23 Apr - 24 Apr
Luxury House Near West Point

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is AED 731
AED 851 total
includes taxes & fees
13 Apr - 14 Apr
Luxury home near West Point

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 AED 597
AED 1,182 total
includes taxes & fees
14 Apr - 15 Apr
Lovely 3BR Home with parking-Walk to WP Gate!

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

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.2 out of 10, Wonderful, (7 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is AED 555
AED 1,707 total
includes taxes & fees
13 Apr - 14 Apr
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.2 out of 10, Wonderful, (5 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is AED 576
AED 1,079 total
includes taxes & fees
14 Apr - 15 Apr
Fabulous 3bdrm Home w/parking!

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very Good, (6 reviews)
"Excellent host, house is very clean. The queen and king beds are comfortable. The sound of the brook is relaxing. "
United States
Penny D.
The price is AED 566
AED 1,799 total
includes taxes & fees
13 Apr - 14 Apr
3BR West Point Retreat-3min to Back Gate+ King Bed

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)
"Great stay!"
United States
Kyra S.
The price is AED 1,737
AED 3,713 total
includes taxes & fees
13 Apr - 14 Apr
New Beach Home near Stamford Downtown/Shippan

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 AED 876
AED 1,923 total
includes taxes & fees
12 Apr - 13 Apr
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly

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 AED 985
AED 1,649 total
includes taxes & fees
1 May - 2 May
Luxury 3 BR Near NYC with Easy Parking

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 AED 331
AED 1,147 total
includes taxes & fees
15 Apr - 16 Apr
Modern 1BR Apt / Free Parking / Near NYC

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)
"The house was beautiful, kitchen was new, bathroom is new, bedding and towels were soft and warm. Lots of thoughtful touches like fluffy socks upon arrival, nespresso coffee and lots of instructions and nightlights. Owner was incredibly responsive and we would absolutely stay there again. One of the cleanest places we have ever stayed. "
United States
Claire G.
The price is AED 716
AED 1,471 total
includes taxes & fees
12 Apr - 13 Apr
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Ossining Hotel Reviews