Boardwalk over marshland on the trail at Teatown Lake Reservation in Ossining, New York.

Holiday Homes in Ossining

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

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 €763
includes taxes & fees
14 Jun - 15 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.
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 €1,487
includes taxes & fees
29 Jun - 30 Jun
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, (36 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is €279
includes taxes & fees
14 Jun - 15 Jun
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 €276
includes taxes & fees
14 Jun - 15 Jun
House on the Babbling Brook- Quiet 2BR + King Bed!
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 €369
includes taxes & fees
15 Jun - 16 Jun
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, (14 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is €340
includes taxes & fees
14 Jun - 15 Jun
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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 €349
includes taxes & fees
14 Jun - 15 Jun
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
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 €120
includes taxes & fees
16 Jun - 17 Jun
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
TV, books, offices

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

Bright&Comfy 2bed/1ba in quiet White Plains duplex
White Plains
9.0 out of 10, Wonderful, (7 reviews)
"Location was great! Clean house! Comfy beds! Great space! "
United States
Montana M.
The price is €364
includes taxes & fees
17 Jun - 18 Jun
Bright&Comfy 2bed/1ba in quiet White Plains duplex
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 €367
includes taxes & fees
14 Jun - 15 Jun
Contemporary Cozy Cottage
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 €503
includes taxes & fees
17 Jun - 18 Jun
Cheerful Home in Yonkers NY
Living area

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is €317
includes taxes & fees
29 Jun - 30 Jun
Stamford Hideaway w/ Fire Pit
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)
"Great location and super host. "
United States
James U.
The price is €377
includes taxes & fees
15 Jun - 16 Jun
Sleek Escape: Modern 3 BR- 4 Min from West Point !
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 €355
includes taxes & fees
16 Jun - 17 Jun
Lovely 3BR Home with parking-Walk to WP Gate!
Interior

Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
The price is €247
includes taxes & fees
16 Jun - 17 Jun
Harriman Outdoor Center - Cranberry Cabin
Interior

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.2 out of 10, Wonderful, (25 reviews)
"House was amazing, with a wonderful view. Hosts were responsive and helpful. Will need to come back in summer!"
United States
Scott H.
The price is €718
includes taxes & fees
14 Jun - 15 Jun
Waterview House Walking Distance from Cove Beach
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 €388
includes taxes & fees
16 Jun - 17 Jun
Fabulous 3bdrm Home w/parking!
Interior

Walkable Townhouse with Garage & Yard, 45 min to NYC!

Walkable Townhouse with Garage & Yard, 45 min to NYC!
West Side
9.6 out of 10, Exceptional, (7 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is €595
includes taxes & fees
14 Jun - 15 Jun
Walkable Townhouse with Garage & Yard, 45 min to NYC!
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 €499
includes taxes & fees
23 Jun - 24 Jun
3BR West Point Retreat-3min to Back Gate+ King Bed
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 Hotel Bronx

Royal Hotel Bronx

2/10 Terrible
"Horrible experience. Never again!!"
Christina 1-night trip
Posted 3 hours ago
Royal Hotel Bronx

Find out more about Ossining

Ossining Holiday Homes information

Number of reviews
210
Accommodation
346 Holiday Homes
Lowest Price
€120
Highest Price
€1,487