A wooden boardwalk winding through a forest with autumn foliage.

Ossining Vacation Rentals

  • 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 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

Outdoor banquet area

1. 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!
Interior

2. 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 ￥36,493
￥47,532 total
includes taxes & fees
Aug 30 - Aug 31
Polished 1BR w/ Accessible Room Features + Sauna
House | 5 bedrooms

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 ￥103,188
￥190,466 total
includes taxes & fees
Sep 1 - Sep 2
Summer Pool Oasis Custom Bar Arcade Pool Table
Interior

4. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is ￥36,661
￥46,713 total
includes taxes & fees
Aug 31 - Sep 1
1BR Queen near NYC | Trails, Biking & Sauna Bliss
Smart TV, video games, DVD player, books

5. '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!
Desk, WiFi (free), bed sheets

6. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Ann S.
The price is ￥22,861
￥47,385 total
includes taxes & fees
Sep 3 - Sep 4
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Dining

7. 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
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 ￥35,856
￥64,755 total
includes taxes & fees
Sep 7 - Sep 8
Luxury NYC Home Game Room Free Parking
Luxury Apartment | Private kitchen

9. 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 ￥28,542
￥56,391 total
includes taxes & fees
Sep 7 - Sep 8
Elegant Hideaway with Free Parking
3 bedrooms, iron/ironing board, internet, bed sheets

10. 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 ￥40,159
￥83,844 total
includes taxes & fees
Aug 31 - Sep 1
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
Property grounds

11. 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
Luxury Villa, Garden View | Dining

12. 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 ￥35,856
￥68,459 total
includes taxes & fees
Sep 7 - Sep 8
Luxury NYC Home with Free Parking for 12
Property grounds

13. 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 ￥31,553
￥53,462 total
includes taxes & fees
Sep 1 - Sep 2
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Dining

14. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is ￥35,856
￥63,679 total
includes taxes & fees
Aug 31 - Sep 1
Prime Luxe 3-BR NYC - Free Parking
Interior

15. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is ￥31,235
￥36,205 total
includes taxes & fees
Aug 31 - Sep 1
Harriman Outdoor Center - Mountain Laurel Cabin
Private kitchen

16. Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC

Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
White Plains
The price is ￥40,159
￥83,844 total
includes taxes & fees
Aug 31 - Sep 1
Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
Apartment (1 Bedroom) | Interior

17. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
TV

18. 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 ￥23,192
￥43,345 total
includes taxes & fees
Aug 31 - Sep 1
Walk to WP Gate + Free Parking!
Exterior

19. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (168 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is ￥24,095
￥27,709 total
includes taxes & fees
Aug 31 - Sep 1
Stamford Suites
Luxury House | Living area

20. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.8 out of 10, Excellent, (3 reviews)
"My family and I were satisfy with the stay I’ll definitely coming back"
United States
Josephine
The price is ￥35,856
￥63,859 total
includes taxes & fees
Sep 7 - Sep 8
Spacious 3BR Luxe Escape near NYC
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

Ethan Allen Hotel

Ethan Allen Hotel

8/10 Good
"It's a nice old hotel that could use a major make over. The price was reasonable around $150.00 staff was great although the front desk didn't help us with our receipt for incidentals which was strange. The bar is nice and the breakfast buffet was good enough for $14.00 person. All and all I would book again."
Donna 1-night trip
Posted 9 hours ago
Ethan Allen Hotel

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:

  • View our selection of featured holiday rentals in Ossining
  • Use the map to find apartments and other holiday homes in the Ossining neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ossining while they last

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.