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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Ossining holiday homes

House

1. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is £937
includes taxes & fees
8 Sept - 9 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table
Outdoor banquet area

2. 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, (9 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is £742
includes taxes & fees
8 Sept - 9 Sept
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Private kitchen

3. 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 £339
includes taxes & fees
30 Sept - 1 Oct
Contemporary Cozy Cottage
Interior

4. Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
The price is £214
includes taxes & fees
7 Sept - 8 Sept
Harriman Outdoor Center - Cranberry Cabin
Interior

5. 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 £348
includes taxes & fees
29 Sept - 30 Sept
Lovely 3BR Home with parking-Walk to WP Gate!
Outdoor dining

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

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
The price is £368
includes taxes & fees
8 Sept - 9 Sept
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Room

7. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
The price is £396
includes taxes & fees
16 Sept - 17 Sept
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
Terrace/patio

8. 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 £331
includes taxes & fees
17 Sept - 18 Sept
House on the Babbling Brook- Quiet 2BR + King Bed!
Property grounds

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)
"This is a beautiful property. Great location. And the hosts are very nice and very great in communicating everything. Loved staying there"
United States
Martina F.
The price is £297
includes taxes & fees
20 Sept - 21 Sept
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Room

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 £103
includes taxes & fees
14 Sept - 15 Sept
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Property grounds

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 £384
includes taxes & fees
9 Sept - 10 Sept
3BR West Point Retreat-3min to Back Gate+ King Bed
Terrace/patio

12. 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, (9 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is £269
includes taxes & fees
7 Sept - 8 Sept
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Property grounds

13. 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, (18 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is £294
includes taxes & fees
28 Sept - 29 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Room

14. 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 £338
includes taxes & fees
9 Sept - 10 Sept
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Luxury Apartment | Living area

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 £277
includes taxes & fees
6 Sept - 7 Sept
Luxury 3 BR Near NYC with Easy Parking
Living area

16. 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 £405
includes taxes & fees
16 Sept - 17 Sept
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
Exterior detail

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 £334
includes taxes & fees
29 Sept - 30 Sept
Fabulous 3bdrm Home w/parking!
Private kitchen

18. 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 £380
includes taxes & fees
9 Sept - 10 Sept
Home away from home
House | Living area

19. 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 £317
includes taxes & fees
8 Sept - 9 Sept
Modern Luxury Home w GameRoom & Parking
Outdoor spa tub

20. 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, (13 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is £293
includes taxes & fees
9 Sept - 10 Sept
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
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

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Muy lindo hotel, limpio y con gran desayuno. El hall es impresionante y los jardines muy lindos. El gym chico pero sirve. Le falta a la zona un poco mas de opciones de comida. Pero vale la pena."
Jose roman 2-night trip
Posted 1 hour ago
Crowne Plaza Suffern - Mahwah by IHG

Find out more about Ossining

Ossining Holiday Homes information

Number of reviews
207
Accommodation
305 Holiday Homes
Lowest Price
£103
Highest Price
£937