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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 1,623
AED 3,371 total
includes taxes & fees
27 Apr - 28 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 2,136
AED 4,297 total
includes taxes & fees
27 Apr - 28 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, (32 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AED 529
AED 1,064 total
includes taxes & fees
21 Apr - 22 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 882
AED 1,616 total
includes taxes & fees
12 May - 13 May
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

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
21 Apr - 22 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 1,184 total
includes taxes & fees
21 Apr - 22 Apr
Luxury House Near West Point

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 582
AED 1,213 total
includes taxes & fees
28 Apr - 29 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
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is AED 347
AED 495 total
includes taxes & fees
24 Apr - 25 Apr
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

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 2,163 total
includes taxes & fees
21 Apr - 22 Apr
Cheerful Home in Yonkers NY

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 867 total
includes taxes & fees
3 May - 4 May
Luxury home near West Point

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
26 Apr - 27 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)
"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 AED 735
AED 1,506 total
includes taxes & fees
23 Apr - 24 Apr
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

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 590
AED 1,153 total
includes taxes & fees
11 May - 12 May
Fabulous 3bdrm Home w/parking!

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 918
AED 1,659 total
includes taxes & fees
4 May - 5 May
Contemporary Cozy Cottage

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.
New Beach Home near Stamford Downtown/Shippan

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
6.0 out of 10, (7 reviews)
"Property bedding was dirty, carpet dirty, sofas were dirty. Not was listed in the pictures. Asked me for $900 deposit through Zelle. No respond. Expedia needs to investigate this company for false advertising. "
United States
Liliana
The price is AED 702
AED 1,333 total
includes taxes & fees
27 Apr - 28 Apr
Modern Luxury Home w GameRoom & 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 875
AED 1,552 total
includes taxes & fees
23 Apr - 24 Apr
Lovely 3BR Home with parking-Walk to WP Gate!

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Carmel Hamlet
10.0 out of 10, Exceptional, (19 reviews)
"Place was beautifully done, it’s obvious they take care of their place. The hosts were thoughtful and attentive, will definitely visit again. "
United States
Jasmine G.
The price is AED 1,980
AED 3,591 total
includes taxes & fees
21 Apr - 22 Apr
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

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

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 613
AED 1,762 total
includes taxes & fees
17 May - 18 May
Sleek Escape: Modern 3 BR- 4 Min from West Point !
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