A wooden boardwalk winding through a forest with autumn foliage.

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Ossining holiday homes

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 HK$5,498
HK$9,717 total
includes taxes & fees
27 Jul - 28 Jul
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
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 HK$8,074
HK$12,775 total
includes taxes & fees
27 Jul - 28 Jul
Summer Pool Oasis Custom Bar Arcade Pool Table
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, (41 reviews)
"rooms were lovely and spacious and hosts were responsive and helpful. "
United States
nina a.
The price is HK$1,482
HK$2,723 total
includes taxes & fees
27 Jul - 28 Jul
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, (10 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$980
HK$3,137 total
includes taxes & fees
22 Jul - 23 Jul
House on the Babbling Brook- Quiet 2BR + King Bed!
1 bedroom, iron/ironing board, free WiFi, bed sheets

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 HK$741
HK$1,057 total
includes taxes & fees
21 Jul - 22 Jul
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Iron/ironing board, Internet, bed sheets

Spacious 3BR Home • Free Parking • Ideal for Families & Groups • Easy NYC Access

Spacious 3BR Home • Free Parking • Ideal for Families & Groups • Easy NYC Access
White Plains
The price is HK$3,175
HK$5,685 total
includes taxes & fees
23 Jul - 24 Jul
Spacious 3BR Home • Free Parking • Ideal for Families & Groups • Easy NYC Access
Coffee/tea maker, fridge, microwave, oven

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (35 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is HK$1,764
HK$3,309 total
includes taxes & fees
2 Aug - 3 Aug
Contemporary Cozy Cottage
Iron/ironing board, Internet, bed sheets

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
The price is HK$3,881
HK$6,519 total
includes taxes & fees
22 Jul - 23 Jul
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
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 HK$972
HK$3,646 total
includes taxes & fees
21 Jul - 22 Jul
3BR West Point Retreat-3min to Back Gate+ King Bed
In-room safe, iron/ironing board, travel cot, 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 HK$2,082
HK$4,381 total
includes taxes & fees
22 Jul - 23 Jul
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
Terrace/patio

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
9.8 out of 10, Exceptional, (8 reviews)
"We had such a nice and peaceful stay! Shelton’s place was super clean, quiet, comfortable, and had everything we needed. Would definitely stay here again! "
United States
Katie M.
The price is HK$1,192
HK$2,798 total
includes taxes & fees
6 Aug - 7 Aug
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
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, (10 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is HK$1,529
HK$3,177 total
includes taxes & fees
22 Jul - 23 Jul
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Living area

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 HK$1,960
HK$4,579 total
includes taxes & fees
21 Jul - 22 Jul
Cheerful Home in Yonkers NY
Smart TV

Spacious 2 Bedroom Home / Parking Included / Near NYC

Spacious 2 Bedroom Home / Parking Included / Near NYC
Bryn Mawr
The price is HK$2,110
HK$4,395 total
includes taxes & fees
1 Aug - 2 Aug
Spacious 2 Bedroom Home / Parking Included / Near NYC
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (9 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is HK$1,445
HK$2,700 total
includes taxes & fees
23 Jul - 24 Jul
Fabulous 3bdrm Home w/parking!
Living area

Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC

Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
White Plains
The price is HK$7,056
HK$10,465 total
includes taxes & fees
22 Jul - 23 Jul
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
Smart TV

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 HK$3,175
HK$5,853 total
includes taxes & fees
27 Jul - 28 Jul
Perfect Family Getaway / 5BR Home / 6 Queen Beds / Free Parking
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 HK$1,460
HK$2,772 total
includes taxes & fees
21 Jul - 22 Jul
Lovely 3BR Home with parking-Walk to WP Gate!
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, (17 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$1,588
HK$3,089 total
includes taxes & fees
22 Jul - 23 Jul
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
9.8 out of 10, Exceptional, (16 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,937
HK$3,505 total
includes taxes & fees
19 Aug - 20 Aug
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

8/10 Good
"The location and property were wonderful. The majority of the staff were friendly and polite, but the staff behind the check in desk could really use some classes on customer service and professionalism in the hospitality sector. Over my stay I had the opportunity to speak and overhear a total of four front desk employees. Not a single smile, no welcome or good afternoon…just basically gave off the impression that they hated their job and didn’t want to be there. The staff who prepared the food for breakfast were 100% more friendly and polite. Hope the right person from corporate sees this."
Wade 1-night trip
Posted 1 hour ago
Baymont by Wyndham White Plains - Elmsford

Find out more about Ossining

Ossining Vacation Homes information

Number of reviews
160
Accommodation
305 Vacation Homes
Lowest Price
HK$1,057
Highest Price
HK$12,775

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