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 1,341
AED 3,043 total
includes taxes & fees
30 Mar - 31 Mar
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Summer at Westchester - Games Pet Friendly Events

Summer at Westchester - Games Pet Friendly Events
2.0 star property
Ossining
The price is AED 1,795
AED 3,694 total
includes taxes & fees
30 Mar - 31 Mar
Summer at Westchester - Games Pet Friendly Events

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 579
AED 1,191 total
includes taxes & fees
30 Mar - 31 Mar
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
9.8 out of 10, Exceptional, (28 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AED 545
AED 1,061 total
includes taxes & fees
31 Mar - 1 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 612
AED 1,304 total
includes taxes & fees
29 Mar - 30 Mar
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

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 661
AED 1,304 total
includes taxes & fees
29 Mar - 30 Mar
Luxury NY Home with Free Parking

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
7.2 out of 10, Good, (5 reviews)
"This was an excellent House My birthday weekend was amazing I totally would book again"
United States
Keisheena
The price is AED 661
AED 1,287 total
includes taxes & fees
29 Mar - 30 Mar
Modern Luxury Home w GameRoom & Parking

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
27 Mar - 28 Mar
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

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 591
AED 1,208 total
includes taxes & fees
29 Mar - 30 Mar
Luxury 3 BR Near NYC with Easy 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 AED 918
AED 2,145 total
includes taxes & fees
27 Mar - 28 Mar
Cheerful Home in Yonkers NY

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.
Waterview House Walking Distance from Cove Beach

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 1,348
AED 3,188 total
includes taxes & fees
29 Mar - 30 Mar
New Beach Home near Stamford Downtown/Shippan

Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
The price is AED 782
AED 2,041 total
includes taxes & fees
30 Mar - 31 Mar
Spacious Retreat with Game Room and Fire Pit

Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (25 reviews)
"A very nice house, with excellent service and an unbeatable location. We had a great time."
Mexico
Armando V.
The price is AED 1,208
AED 2,797 total
includes taxes & fees
29 Mar - 30 Mar
Stylish Beach Home near Stamford Downtown/Beach

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 735
AED 1,668 total
includes taxes & fees
29 Mar - 30 Mar
Luxury NYC Retreat with Free Parking

Luxury NY Retreat+Free Parking

Luxury NY Retreat+Free Parking
White Plains
The price is AED 661
AED 1,483 total
includes taxes & fees
29 Mar - 30 Mar
Luxury NY Retreat+Free Parking

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)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveler
The price is AED 661
AED 1,287 total
includes taxes & fees
30 Mar - 31 Mar
3BR Prime Luxury near NYC w Arcade Room

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is AED 826
AED 1,533 total
includes taxes & fees
1 Apr - 2 Apr
Contemporary Cozy Cottage

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, (7 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AED 408
AED 1,370 total
includes taxes & fees
30 Mar - 31 Mar
House on the Babbling Brook- Quiet 2BR + King Bed!
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