A wooden boardwalk winding through a forest with autumn foliage.

Holiday Homes in Ossining

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 July - 12 July
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

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 AU$1,913
includes taxes & fees
29 June - 30 June
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
House

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is AU$2,312
includes taxes & fees
29 June - 30 June
Summer Pool Oasis Custom Bar Arcade Pool Table
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, (9 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AU$558
includes taxes & fees
30 June - 1 July
House on the Babbling Brook- Quiet 2BR + King Bed!
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)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AU$472
includes taxes & fees
5 July - 6 July
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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 AU$580
includes taxes & fees
28 June - 29 June
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Living area

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is AU$479
includes taxes & fees
29 June - 30 June
Stamford Hideaway w/ Fire Pit
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, (14 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is AU$606
includes taxes & fees
29 June - 30 June
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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 AU$198
includes taxes & fees
28 June - 29 June
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 AU$605
includes taxes & fees
5 July - 6 July
Contemporary Cozy Cottage
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, (7 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 AU$509
includes taxes & fees
14 July - 15 July
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, (9 reviews)
"So cute and cozy!! We had the best time and loved it. "
United States
corinne n.
The price is AU$723
includes taxes & fees
22 July - 23 July
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Fridge, microwave, dishwasher, coffee/tea maker

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
White Plains
9.2 out of 10, Wonderful, (15 reviews)
"Great place for a short visit to the city "
United States
Jeremy S.
The price is AU$1,094
includes taxes & fees
22 July - 23 July
3 Mi to Downtown: Spacious White Plains Home
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 AU$703
includes taxes & fees
30 June - 1 July
3BR West Point Retreat-3min to Back Gate+ King Bed
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 AU$729
includes taxes & fees
28 July - 29 July
Lovely 3BR Home with parking-Walk to WP Gate!
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 AU$1,070
includes taxes & fees
28 June - 29 June
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.6 out of 10, Exceptional, (7 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is AU$694
includes taxes & fees
14 July - 15 July
Fabulous 3bdrm Home w/parking!
Interior

Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
The price is AU$436
includes taxes & fees
19 July - 20 July
Harriman Outdoor Center - Cranberry Cabin
TV

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Cove - East Side - Shippan
8.0 out of 10, Very good, (6 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is AU$640
includes taxes & fees
29 June - 30 June
Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Terrace/patio

Spacious 3BR Home • Free Parking • Convenient NYC Access • Perfect for Families

Spacious 3BR Home • Free Parking • Convenient NYC Access • Perfect for Families
Southeast Yonkers
The price is AU$907
includes taxes & fees
30 June - 1 July
Spacious 3BR Home • Free Parking • Convenient NYC Access • Perfect for Families
Smart TV

Cozy 4BR Home • Free Street Parking • Quick NYC Access • Perfect for Families

Cozy 4BR Home • Free Street Parking • Quick NYC Access • Perfect for Families
Southeast Yonkers
The price is AU$1,986
includes taxes & fees
4 July - 5 July
Cozy 4BR Home • Free Street Parking • Quick NYC Access • Perfect for Families
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ossining Hotel Reviews

Royal Regency Hotel

Royal Regency Hotel

10/10 Excellent
"I grew up in the area so I know the reputation of this place before the 21st century. When I was looking to stay in town recently, the Royal Regency came up and looked really nice, renovated and well liked by the reviews. I wasn't sure if I could trust it but I figured let's try it out. Let me tell you that this place was way better than I expected. Really nice renovated rooms, nice staff, easy check in and check out. The only minor thing I would suggest is that they add something to the rooms that allows you to hang things up, there was no closet or hanging rack in my room."
Nicole 3-night trip
Posted 6 hours ago
Royal Regency Hotel

Find out more about Ossining

Ossining Holiday Homes information

Number of reviews
151
Accommodation
353 Holiday Homes
Lowest Price
AU$198
Highest Price
AU$2,312