A wooden boardwalk winding through a forest with autumn foliage.

Ossining Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Ossining vacation rentals

Interior

1. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is ￥39,862
￥50,634 total
includes taxes & fees
Sep 1 - Sep 2
1BR Queen near NYC | Trails, Biking & Sauna Bliss
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 ￥81,646
￥161,345 total
includes taxes & fees
Sep 1 - Sep 2
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
House

3. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is ￥103,660
￥191,337 total
includes taxes & fees
Sep 1 - Sep 2
Summer Pool Oasis Custom Bar Arcade Pool Table
Interior

4. Polished 1BR w/ Accessible Room Features + Sauna

Polished 1BR w/ Accessible Room Features + Sauna
Ossining
6.0 out of 10, (1 review)
"We could not find location in dark and rain. Only given GPS info and no name of hotel or property. Once we arrived guard at guardhouse could not assist as we could not affirm name. When finally able to track down contact info for the vacation property company that listed the rental they had to share hotel front desk info and that’s when we learned name was Windrose On Hudson. Very stressful situation- enjoyed historical location. Great facility, not so great TV/streaming set-up… cable. "
United States
Nada S.
The price is ￥39,862
￥51,923 total
includes taxes & fees
Sep 27 - Sep 28
Polished 1BR w/ Accessible Room Features + Sauna
Dining

5. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is ￥25,742
￥54,526 total
includes taxes & fees
Sep 2 - Sep 3
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Living area

6. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (7 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is ￥38,229
￥71,553 total
includes taxes & fees
Sep 15 - Sep 16
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Property grounds

7. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (21 reviews)
"Great place to stay! "
United States
Megan D.
The price is ￥20,011
￥34,590 total
includes taxes & fees
Sep 28 - Sep 29
Piermont Oasis
Villa, Garden View | Living area

8. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is ￥36,021
￥65,052 total
includes taxes & fees
Sep 1 - Sep 2
Luxury NYC Home Game Room Free Parking
Room

9. 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 ￥40,343
￥84,228 total
includes taxes & fees
Sep 1 - Sep 2
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
Luxury Apartment | Private kitchen

10. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
The price is ￥28,672
￥56,647 total
includes taxes & fees
Sep 1 - Sep 2
Elegant Hideaway with Free Parking
Interior

11. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is ￥31,378
￥36,192 total
includes taxes & fees
Sep 7 - Sep 8
Harriman Outdoor Center - Mountain Laurel Cabin
Property grounds

12. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (141 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥31,698
￥53,707 total
includes taxes & fees
Sep 1 - Sep 2
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior detail

13. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (24 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is ￥25,280
￥76,927 total
includes taxes & fees
Sep 1 - Sep 2
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Room

14. 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 ￥15,129
￥21,587 total
includes taxes & fees
Sep 1 - Sep 2
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Property grounds

15. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
8.0 out of 10, Very Good, (5 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is ￥27,087
￥36,601 total
includes taxes & fees
Sep 12 - Sep 13
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Luxury Villa, Garden View | Dining

16. Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (1 review)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
The price is ￥36,021
￥68,774 total
includes taxes & fees
Sep 1 - Sep 2
Luxury NYC Home with Free Parking for 12
Living area

17. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (25 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
The price is ￥23,298
￥43,543 total
includes taxes & fees
Sep 1 - Sep 2
Walk to WP Gate + Free Parking!
Private kitchen

18. 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 ￥40,023
￥73,242 total
includes taxes & fees
Sep 28 - Sep 29
Contemporary Cozy Cottage
Property grounds

19. Garden Loft with Patios & Green Space · Westchester Retreat

Garden Loft with Patios & Green Space · Westchester Retreat
Scarsdale
9.0 out of 10, Wonderful, (6 reviews)
"It was excellent!! "
United States
Henry C.
The price is ￥31,538
￥57,312 total
includes taxes & fees
Sep 28 - Sep 29
Garden Loft with Patios & Green Space · Westchester Retreat
Dining

20. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is ￥36,021
￥63,970 total
includes taxes & fees
Sep 1 - Sep 2
Prime Luxe 3-BR NYC - Free Parking
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

Armoni Inn & Suites

Armoni Inn & Suites

8/10 Good
"It was okay for a quick stay."
Tanjina 1-night trip
Posted 5 hours ago
Armoni Inn & Suites

Find out more about Ossining

Search for holiday rentals in Ossining on Expedia! You can easily find your home rentals, villas, holiday apartments in Ossining using one of the methods below:

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Look no further and take a look at our great range of rental properties in Ossining!

Frequently asked questions

Can I find a vacation rental in Ossining?

Yes, there are vacation rentals in Ossining close to Labyrinth, or you can select a more remote option if you'd like a relaxing place to stay. Ossining is known for its restaurants and parks. Make sure you have time to check out the golf courses and university setting during your trip.

What's the top vacation rental that Ossining has to offer?

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!: This highly rated vacation home rental in Ossining is located near skiing and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Ossining?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Ossining stay.

What’s there to see and do in Ossining?

Cultural attractions include Sing Sing Prison Museum and Ossining Historical Society, whereas Teatown Lake Reservation and Merchants Square are a couple of picturesque spots to enjoy the outdoors. Sing Sing Correctional Facility and Ossining Public Library are other places to visit while you're in town.

What’s a vacation rental in Ossining like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Ossining. Vacation rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for families.