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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 1,436
AED 3,153 total
includes taxes & fees
20 Apr - 21 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 1,816
AED 3,718 total
includes taxes & fees
7 Apr - 8 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 579
AED 1,209 total
includes taxes & fees
5 Apr - 6 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
9.8 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 1,554 total
includes taxes & fees
5 Apr - 6 Apr
Contemporary Cozy Cottage

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
5 Apr - 6 Apr
Luxury NY Home with Free Parking

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 580
AED 1,750 total
includes taxes & fees
5 Apr - 6 Apr
Sleek Escape: Modern 3 BR- 4 Min from West Point !

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
6 Apr - 7 Apr
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

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 514
AED 1,733 total
includes taxes & fees
4 Apr - 5 Apr
3BR West Point Retreat-3min to Back Gate+ King Bed

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 665
AED 1,291 total
includes taxes & fees
5 Apr - 6 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 481
AED 1,470 total
includes taxes & fees
5 Apr - 6 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 home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (1 review)
The price is AED 731
AED 851 total
includes taxes & fees
7 Apr - 8 Apr
Luxury home near West Point

Cozy 1-bedroom house in beautiful Yonkers with AC

Cozy 1-bedroom house in beautiful Yonkers with AC
Lincoln Park
The price is AED 364
AED 835 total
includes taxes & fees
10 Apr - 11 Apr
Cozy 1-bedroom house in beautiful Yonkers with AC

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 1,219
AED 2,821 total
includes taxes & fees
7 Apr - 8 Apr
Waterview House Walking Distance from Cove Beach

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 744
AED 1,586 total
includes taxes & fees
7 Apr - 8 Apr
Comfortable 3BR Home / 4 Queen Beds / Free Parking / Perfect for Groups

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 826
AED 1,773 total
includes taxes & fees
7 Apr - 8 Apr
Luxury NYC Retreat with Free Parking

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 621
AED 1,191 total
includes taxes & fees
14 Apr - 15 Apr
Lovely 3BR Home with parking-Walk to WP Gate!

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 735
AED 1,369 total
includes taxes & fees
6 Apr - 7 Apr
3BR Prime Luxury near NYC w Arcade Room
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