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 1,480
AED 3,191 total
includes taxes & fees
7 Apr - 8 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 1,837
AED 3,743 total
includes taxes & fees
8 Apr - 9 Apr
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, (29 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AED 493
AED 996 total
includes taxes & fees
7 Apr - 8 Apr
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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
7 Apr - 8 Apr
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

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
7 Apr - 8 Apr
Contemporary Cozy Cottage

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 592
AED 1,243 total
includes taxes & fees
14 Apr - 15 Apr
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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
7 Apr - 8 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 744
AED 1,398 total
includes taxes & fees
9 Apr - 10 Apr
Luxury NY Home with Free Parking

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 739
AED 1,374 total
includes taxes & fees
7 Apr - 8 Apr
Luxury 3 BR Near NYC with Easy 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 459
AED 1,429 total
includes taxes & fees
7 Apr - 8 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 1,192 total
includes taxes & fees
7 Apr - 8 Apr
Luxury House Near West Point

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 AED 918
AED 1,844 total
includes taxes & fees
3 May - 4 May
Luxury NYC Retreat with Free Parking

Comfortable 3BR Home / 4 Queen Beds / Free Parking / Perfect for Groups

Comfortable 3BR Home / 4 Queen Beds / Free Parking / Perfect for Groups
White Plains
The price is AED 876
AED 1,758 total
includes taxes & fees
7 Apr - 8 Apr
Comfortable 3BR Home / 4 Queen Beds / Free Parking / Perfect for Groups

Spacious 2 Bedroom Home / Parking Included / Near NYC

Spacious 2 Bedroom Home / Parking Included / Near NYC
Bryn Mawr
The price is AED 493
AED 1,389 total
includes taxes & fees
7 Apr - 8 Apr
Spacious 2 Bedroom Home / Parking Included / Near NYC

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"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
7 Apr - 8 Apr
Luxury home near West Point

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 478
AED 1,618 total
includes taxes & fees
7 Apr - 8 Apr
Sleek Escape: Modern 3 BR- 4 Min from 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 601
AED 1,162 total
includes taxes & fees
13 Apr - 14 Apr
Lovely 3BR Home with parking-Walk to WP Gate!

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 536
AED 1,762 total
includes taxes & fees
7 Apr - 8 Apr
3BR West Point Retreat-3min to Back Gate+ King Bed

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.2 out of 10, Wonderful, (22 reviews)
"Great location for visiting Stamford, right on the water, a short walk from the beach, a short drive from the ShopRite. Liked the pool table. Excellent kitchen. Backyard seemed very nice but didn't use it due to weather. Easily parks 5 cars, and off-season (Oct-Apr) there is parking at the beach nearby."
United States
Eric K.
The price is AED 1,172
AED 2,761 total
includes taxes & fees
7 Apr - 8 Apr
Waterview House Walking Distance from Cove Beach

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 580
AED 1,108 total
includes taxes & fees
13 Apr - 14 Apr
Fabulous 3bdrm Home w/parking!
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