Holiday Homes in Ossining

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

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 €868
includes taxes & fees
19 Mar - 20 Mar
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Villa

NEW 45 Wolden Rd Ossining NY 10562

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
Ossining
The price is €933
includes taxes & fees
15 Mar - 16 Mar
NEW 45 Wolden Rd Ossining NY 10562
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
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is €283
includes taxes & fees
4 Mar - 5 Mar
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is €300
includes taxes & fees
4 Mar - 5 Mar
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is €228
includes taxes & fees
9 Mar - 10 Mar
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is €355
includes taxes & fees
11 Mar - 12 Mar
Contemporary Cozy Cottage
Property grounds

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, (6 reviews)
The price is €342
includes taxes & fees
4 Mar - 5 Mar
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
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, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is €281
includes taxes & fees
4 Mar - 5 Mar
House on the Babbling Brook- Quiet 2BR + King Bed!
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
9.8 out of 10, Exceptional, (6 reviews)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is €355
includes taxes & fees
4 Mar - 5 Mar
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)
"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 €366
includes taxes & fees
4 Mar - 5 Mar
3BR West Point Retreat-3min to Back Gate+ King Bed
Outdoor dining

45 Minutes from NYC, Entire House near Stamford Downtown,

45 Minutes from NYC, Entire House near Stamford Downtown,
Downtown Stamford
10.0 out of 10, Exceptional, (22 reviews)
"The house was excellent in accomadations, cleanliness and location."
United States
Rene M.
The price is €329
includes taxes & fees
5 Mar - 6 Mar
45 Minutes from NYC, Entire House near Stamford Downtown,
Living area

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 €490
includes taxes & fees
4 Mar - 5 Mar
Luxury 3 BR Near NYC with Easy 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 €300
includes taxes & fees
23 Mar - 24 Mar
Lovely 3BR Home with parking-Walk to WP Gate!
Property grounds

Comfortable 1 family home in Tuckahoe that's near train

Comfortable 1 family home in Tuckahoe that's near train
Tuckahoe
The price is €595
includes taxes & fees
15 Mar - 16 Mar
Comfortable 1 family home in Tuckahoe that's near train
TV

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (3 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is €377
includes taxes & fees
4 Mar - 5 Mar
Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Exterior detail

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 €247
includes taxes & fees
4 Mar - 5 Mar
Fabulous 3bdrm Home w/parking!
WiFi, bed sheets

Cozy 1-bedroom house in beautiful Yonkers with AC

Cozy 1-bedroom house in beautiful Yonkers with AC
Lincoln Park
The price is €235
includes taxes & fees
15 Mar - 16 Mar
Cozy 1-bedroom house in beautiful Yonkers with AC
Smart TV, fireplace, video games, DVD player

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)
"Lovely house with all the amenities. We had a wonderful time."
United States
Diana P.
The price is €829
includes taxes & fees
5 Mar - 6 Mar
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is €271
includes taxes & fees
4 Mar - 5 Mar
Luxury House Near West Point
Fridge, microwave, oven, stovetop

Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (25 reviews)
"A very nice house, with excellent service and an unbeatable location. We had a great time."
Mexico
Armando V.
The price is €652
includes taxes & fees
4 Mar - 5 Mar
Stylish Beach Home near Stamford Downtown/Beach
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
"The hotel is stunning and my room was beautiful and spotless! I was there during the major snowstorm, could not get back home to NYC and this hotel gave me the opportunity to relax, have a drink at the lobby bar and also enjoy a tasty buffet breakfast in the morning! I will gladly recommend to friends who travel to the Westchester area!"
CAROL 1-night trip
Posted 2 days ago
Royal Regency Hotel

Find out more about Ossining

Ossining Holiday Homes information

Number of reviews
166
Accommodation
325 Holiday Homes
Lowest Price
€228
Highest Price
€933