A wooden boardwalk winding through a forest with autumn foliage.

Search Vacation 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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Ossining vacation homes

A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

1. NYC-Area Escape Near River, Trails & MTA!

NYC-Area Escape Near River, Trails & MTA!
Ossining
8.2 out of 10, Very Good, (19 reviews)
"A family trip with teens and tweens- a perfect space! Clean, hist was friendly, the house was stocked with all we'd need! A great getaway for any family NYC trip!"
United States
Justeen P.
The price is ￥33,730
￥126,363 total
includes taxes & fees
Sep 15 - Sep 16
NYC-Area Escape Near River, Trails & MTA!
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is ￥101,029
￥189,091 total
includes taxes & fees
Sep 14 - Sep 15
Summer Pool Oasis Custom Bar Arcade Pool Table
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

3. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is ￥78,193
￥152,814 total
includes taxes & fees
Sep 14 - Sep 15
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

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

Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
White Plains
2.0 out of 10, (1 review)
"An hour before check-in we were called by the property manager, after four days of messaging them through the app without response, to advise us that the property had an alleged water pipe burst and was unavailable, then attempted to upcharge us for alternate accommodations. An alternate place to stay was finally provided at no additional charge but much smaller than what had been booked. Given the absence of communication for four days and then a sudden incident the day of check-in - the day...
United States
James D.
The price is ￥41,396
￥84,174 total
includes taxes & fees
Sep 13 - Sep 14
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

5. 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, (11 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥19,165
￥61,336 total
includes taxes & fees
Sep 13 - Sep 14
House on the Babbling Brook- Quiet 2BR + King Bed!
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

6. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (40 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 ￥38,330
￥66,987 total
includes taxes & fees
Sep 30 - Oct 1
Contemporary Cozy Cottage
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

7. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
The price is ￥28,824
￥77,807 total
includes taxes & fees
Oct 7 - Oct 8
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A wooden cabin with large windows, a wooden bench, and a view of the forest.

8. Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
The price is ￥37,410
￥43,386 total
includes taxes & fees
Sep 14 - Sep 15
Harriman Outdoor Center - Cranberry Cabin
A campfire with a wooden table and benches by a lake.

9. 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, (42 reviews)
"Nice stay"
United States
Christopher J.
The price is ￥36,030
￥62,439 total
includes taxes & fees
Sep 27 - Sep 28
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

10. 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 ￥14,489
￥20,674 total
includes taxes & fees
Sep 15 - Sep 16
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A blue house with a white porch, a welcome sign, and a mailbox.

11. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very Good, (7 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 ￥22,231
￥75,277 total
includes taxes & fees
Sep 13 - Sep 14
3BR West Point Retreat-3min to Back Gate+ King Bed
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

12. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay at the lake house. The home is beautiful inside and out, and there is every amenity you could think of, from cooking and cleaning supplies to extra towels and blankets. The view of the lake is stunning and we enjoyed the peace and quiet of the little community. Linh is an excellent host and helped answer all of our questions. We will definitely be back!"
United States
Angel R.
The price is ￥43,696
￥88,844 total
includes taxes & fees
Sep 15 - Sep 16
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
An outdoor patio with a fire pit, green chairs, and a table.

13. 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, (10 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is ￥22,998
￥54,364 total
includes taxes & fees
Oct 5 - Oct 6
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

14. 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, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is ￥29,529
￥57,723 total
includes taxes & fees
Sep 15 - Sep 16
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

15. 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 ￥55,503
￥84,938 total
includes taxes & fees
Sep 30 - Oct 1
Luxury 3 BR Near NYC with Easy Parking
A room with a wooden floor, a white door with a number, and a window with blinds.

16. 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 ￥41,534
￥71,494 total
includes taxes & fees
Sep 22 - Sep 23
Lovely 3BR Home with parking-Walk to WP Gate!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

17. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is ￥40,568
￥68,310 total
includes taxes & fees
Sep 14 - Sep 15
Fabulous 3bdrm Home w/parking!
A modern living room with a white sofa, a glass coffee table, and a marble-patterned rug.

18. Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
4.6 out of 10, (11 reviews)
"Don’t stay here. Not as listed. "
United States
Kenyon
The price is ￥38,330
￥65,728 total
includes taxes & fees
Sep 13 - Sep 14
Modern Luxury Home w GameRoom & Parking
A deck with Adirondack chairs, a fire pit, and a grill.

19. 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, (14 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is ￥29,897
￥61,397 total
includes taxes & fees
Sep 14 - Sep 15
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

20. Home away from home

Home away from home
Dumont
9.0 out of 10, Wonderful, (7 reviews)
"Jennifer was amazing! She accommodated us even with our very last minute request. The place was spotless and Jennifer was so helpful. Just an awesome experience! I will definitely book it again!"
United States
Elisa G.
The price is ￥47,223
￥77,800 total
includes taxes & fees
Sep 12 - Sep 13
Home away from home
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

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"Great hotel. Super clean and staff is very friendly. Rooms are a little dated but very big. And very well maintained and very clean."
Dan 1-night trip
Posted 2 hours ago
Hyatt Regency Greenwich

Find out more about Ossining

Ossining Vacation Homes information

Number of reviews
231
Accommodation
276 Vacation Homes
Lowest Price
￥20,674
Highest Price
￥189,091