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Check prices for these dates

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

Our top choices for Ossining holiday 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 £667
includes taxes & fees
31 May - 1 Jun
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 £1,114
includes taxes & fees
23 Jun - 24 Jun
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 £1,269
includes taxes & fees
23 Jun - 24 Jun
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, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is £292
includes taxes & fees
2 Jun - 3 Jun
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, (36 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is £240
includes taxes & fees
1 Jun - 2 Jun
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
9.2 out of 10, Wonderful, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is £256
includes taxes & fees
1 Jun - 2 Jun
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Outdoor dining

Stamford : The Comfy Cove Hideout

Stamford : The Comfy Cove Hideout
Cove - East Side - Shippan
Stamford : The Comfy Cove Hideout
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 £103
includes taxes & fees
1 Jun - 2 Jun
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
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 £318
includes taxes & fees
31 May - 1 Jun
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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 £459
includes taxes & fees
8 Jun - 9 Jun
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
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 £432
includes taxes & fees
5 Jun - 6 Jun
Cheerful Home in Yonkers NY
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 £315
includes taxes & fees
2 Jun - 3 Jun
Contemporary Cozy Cottage
TV

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
Highland Falls
10.0 out of 10, Exceptional, (33 reviews)
"Great location, good communication, and wonderfully appointed."
United States
george l.
The price is £422
includes taxes & fees
2 Jun - 3 Jun
Updated Home w/ Patio Half Mile to West Point
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.
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Fridge, microwave, oven, stovetop

Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
The price is £529
includes taxes & fees
2 Jun - 3 Jun
Spacious Retreat with Game Room and 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 £519
includes taxes & fees
31 May - 1 Jun
Spacious 3BR Home / Free Parking / Perfect for Families & Groups
In-room safe, iron/ironing board, travel cot, free WiFi

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 £525
includes taxes & fees
31 May - 1 Jun
Perfect Family Getaway / 5BR Home / 6 Queen Beds / Free Parking
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 £368
includes taxes & fees
2 Jun - 3 Jun
3BR West Point Retreat-3min to Back Gate+ King Bed
Interior

Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
The price is £211
includes taxes & fees
31 May - 1 Jun
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 £294
includes taxes & fees
8 Jun - 9 Jun
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

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

8/10 Good
"I came in late at night. Staff was nice."
Baila 1-night trip
Posted 6 hours ago
Hampton Inn White Plains/Tarrytown

Find out more about Ossining

Ossining Holiday Homes information

Number of reviews
156
Accommodation
352 Holiday Homes
Lowest Price
£103
Highest Price
£1,269