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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Ossining vacation homes

Fridge, microwave, stovetop, dishwasher

NYC-Area Escape Near River, Trails & MTA!

NYC-Area Escape Near River, Trails & MTA!
Ossining
8.2 out of 10, Very Good, (15 reviews)
"Host was very communicative. "
United States
Joe W.
The price is ￥43,481
￥140,926 total
includes taxes & fees
Jun 14 - Jun 15
NYC-Area Escape Near River, Trails & MTA!
Outdoor banquet area

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 ￥143,343
￥234,963 total
includes taxes & fees
Jun 23 - Jun 24
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
House, Smoking | 5 bedrooms

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is ￥172,651
￥266,438 total
includes taxes & fees
Jun 23 - Jun 24
Summer Pool Oasis Custom Bar Arcade Pool Table
TV, fireplace

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)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥35,836
￥67,145 total
includes taxes & fees
Jun 1 - Jun 2
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Property grounds

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
9.2 out of 10, Wonderful, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥28,525
￥57,491 total
includes taxes & fees
Jun 1 - Jun 2
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

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, (36 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is ￥27,235
￥51,388 total
includes taxes & fees
Jun 3 - Jun 4
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Terrace/patio

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 ￥19,909
￥61,945 total
includes taxes & fees
Jun 2 - Jun 3
House on the Babbling Brook- Quiet 2BR + King Bed!
Terrace/patio

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 ￥15,051
￥21,476 total
includes taxes & fees
Jun 1 - Jun 2
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥35,836
￥66,855 total
includes taxes & fees
Jun 1 - Jun 2
Contemporary Cozy Cottage
TV, books, offices

Bright&Comfy 2bed/1ba in quiet White Plains duplex

Bright&Comfy 2bed/1ba in quiet White Plains duplex
White Plains
8.8 out of 10, Excellent, (6 reviews)
"Location was great! Clean house! Comfy beds! Great space! "
United States
Montana M.
The price is ￥37,428
￥66,261 total
includes taxes & fees
Jun 17 - Jun 18
Bright&Comfy 2bed/1ba in quiet White Plains duplex
3 bedrooms, desk, iron/ironing board, free WiFi

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)
"Very nice apartment in Highland Falls. Each bedroom has nice closet space and the master is very large. Remodeled very well and comfortable. "
United States
chris f.
The price is ￥21,501
￥71,665 total
includes taxes & fees
Jun 9 - Jun 10
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Property grounds

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)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is ￥20,227
￥72,614 total
includes taxes & fees
Jun 2 - Jun 3
3BR West Point Retreat-3min to Back Gate+ King Bed
In-room safe, iron/ironing board, travel crib, free WiFi

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 ￥50,170
￥99,397 total
includes taxes & fees
Jun 1 - Jun 2
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
Hair dryer, bidet, towels, soap

Perfect Family Getaway / 5BR Home / 6 Queen Beds / Free Parking

Perfect Family Getaway / 5BR Home / 6 Queen Beds / Free Parking
Bryn Mawr
The price is ￥78,839
￥138,220 total
includes taxes & fees
Jun 1 - Jun 2
Perfect Family Getaway / 5BR Home / 6 Queen Beds / Free Parking
Living area

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
Stamford Hideaway w/ Fire Pit
Dining

Spacious 3BR Home / Free Parking / Perfect for Families & Groups

Spacious 3BR Home / Free Parking / Perfect for Families & Groups
White Plains
The price is ￥64,504
￥115,493 total
includes taxes & fees
Jun 1 - Jun 2
Spacious 3BR Home / Free Parking / Perfect for Families & Groups
Outdoor spa tub

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, (9 reviews)
"So cute and cozy!! We had the best time and loved it. "
United States
corinne n.
The price is ￥38,543
￥74,126 total
includes taxes & fees
Jun 15 - Jun 16
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Interior

Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
The price is ￥38,862
￥45,070 total
includes taxes & fees
Jun 4 - Jun 5
Harriman Outdoor Center - Cranberry Cabin
Interior

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 ￥35,454
￥63,979 total
includes taxes & fees
Jun 7 - Jun 8
Lovely 3BR Home with parking-Walk to WP Gate!
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

Royal Regency Hotel

Royal Regency Hotel

10/10 Excellent
"Great stay"
Denis 2-night trip
Posted less than an hour ago
Royal Regency Hotel

Find out more about Ossining

Ossining Vacation Homes information

Number of reviews
173
Accommodation
307 Vacation Homes
Lowest Price
￥21,476
Highest Price
￥266,438