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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Ossining vacation rentals

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.

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 AED 1,802
AED 3,748 total
includes taxes & fees
9 Nov - 10 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern living room with a large window, a sofa with patterned cushions, a wooden coffee table, and a painting on the wall.

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, (10 reviews)
"It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it."
United States
Karen O.
The price is AED 1,299
AED 2,844 total
includes taxes & fees
9 Nov - 10 Nov
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
An aerial view of a campus with multiple buildings, a central courtyard, and a lake in the background.

3. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is AED 930
AED 1,072 total
includes taxes & fees
15 Nov - 16 Nov
1BR Queen near NYC | Trails, Biking & Sauna Bliss
An aerial view of a campus with multiple buildings, a central courtyard, and a lake in the background.

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 AED 930
AED 1,072 total
includes taxes & fees
15 Nov - 16 Nov
Polished 1BR w/ Accessible Room Features + Sauna
A stone staircase leading to a house with a stone wall and a metal gate.

5. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (28 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is AED 918
AED 1,483 total
includes taxes & fees
9 Nov - 10 Nov
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

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, (9 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 AED 917
AED 1,603 total
includes taxes & fees
19 Nov - 20 Nov
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A nighttime view of a residential street with houses, trees, and parked cars.

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, (95 reviews)
"The host, Maria, was excellent in staying in touch and personally met me upon check-in and checkout. The location is very convenient for walking around downtown or easily drive to nearby outings."
United States
Margaret S.
The price is AED 728
AED 1,299 total
includes taxes & fees
12 Nov - 13 Nov
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A modern hotel lobby with a stone wall, a coffee machine, a refrigerator, and a sign advertising a motel.

8. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
10.0 out of 10, Exceptional, (1 review)
"Beds were adequate, nothing special but perfectly fine for a short overnight stay."
United States
Anonymous traveler
The price is AED 424
AED 485 total
includes taxes & fees
10 Nov - 11 Nov
1 Queen Bed | Smoking
A wooden staircase leading to a small shed with a slanted roof, surrounded by dense greenery and a stone wall.

9. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (24 reviews)
"Great place to stay! "
United States
Megan D.
The price is AED 441
AED 736 total
includes taxes & fees
16 Nov - 17 Nov
Piermont Oasis
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

10. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (42 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
The price is AED 826
AED 1,470 total
includes taxes & fees
10 Nov - 11 Nov
Contemporary Cozy Cottage
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

11. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (208 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
United States
Christine
The price is AED 585
AED 672 total
includes taxes & fees
8 Nov - 9 Nov
Stamford Suites
A house with a view of a bridge and mountains.

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, (150 reviews)
"We had a great stay!!"
United States
Jasmine
The price is AED 727
AED 1,158 total
includes taxes & fees
7 Dec - 8 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A breakfast buffet with pastries, fruits, and a coffee station.

13. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is AED 3,306
AED 4,229 total
includes taxes & fees
8 Nov - 9 Nov
3BR Prime Luxury NY - Free Parking
A historic building with a central tower labeled 'West Point Museum,' featuring a traditional architectural style with multiple windows and a stone facade.

14. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is AED 452
AED 1,098 total
includes taxes & fees
9 Nov - 10 Nov
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A room with large windows overlooking a lake and greenery.

15. 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, (46 reviews)
"Nice stay"
United States
Christopher J.
The price is AED 645
AED 1,241 total
includes taxes & fees
8 Nov - 9 Nov
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A wooden staircase leading to a gazebo in a forested area with a metal railing.

16. 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
8.6 out of 10, Excellent, (7 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 AED 918
AED 1,167 total
includes taxes & fees
26 Nov - 27 Nov
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
A hallway with a wooden door, a black table with a sign, and large green plants.

17. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Clean and convenient near West Point golf course"
United States
mario b.
The price is AED 481
AED 1,535 total
includes taxes & fees
11 Nov - 12 Nov
3BR Near West Point | Coffee Bar | Sleeps 6
A modern hotel lobby with a stone wall, a coffee machine, a refrigerator, and a sign advertising a motel.

18. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (2 reviews)
"Our rooms felt cozy enough for two people with decent privacy due to separate bathrooms nearby too.The location suited our plan moving between airport runs & visits close by malls perfectly."
United States
Anonymous traveler
The price is AED 453
AED 518 total
includes taxes & fees
8 Nov - 9 Nov
1 King Bed | Non-Smoking
A modern interior with a stone wall, a vending machine, a coffee machine, and a sign advertising a motel.

19. 2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (1 review)
"The staff were attentive without being pushy, and the bed provided good comfort."
United States
Anonymous traveler
The price is AED 445
AED 510 total
includes taxes & fees
10 Nov - 11 Nov
2 Full Beds | Non-Smoking
A wooden gazebo with a lattice roof overlooking a forested area with a stream.

20. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is AED 1,208
AED 1,855 total
includes taxes & fees
8 Nov - 9 Nov
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
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

West Gate Inn Nyack

West Gate Inn Nyack

10/10 Excellent
"Everything was good, but the wifi was not that great in the room"
Lakyisha 1-night trip
Posted 16 hours ago
West Gate Inn Nyack

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?

Modern Luxury Home w GameRoom & Parking: You might want to consider this Ossining vacation home rental for your stay. It is situated near the airport and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family. Another good choice for your trip to Ossining is Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!.

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 Louis Engel Waterfront Park and Teatown Lake Reservation are a couple of picturesque spots to enjoy the outdoors. Hudson Hills Golf Course and Thomas J. Watson Research Center 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.