A wooden boardwalk winding through a forest with autumn foliage.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Ossining cottages

A two-story house with a front yard, a staircase, and a covered outdoor seating area.

1. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
The price is €728
includes taxes & fees
21 Oct - 22 Oct
Snow Days & City Escapes: Spacious Ossining Home
A wooden deck with a railing overlooking a body of water and trees.

2. 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, (24 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is €371
includes taxes & fees
18 Oct - 19 Oct
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A house with a view of a bridge and mountains.

3. 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, (147 reviews)
"We had a great stay!!"
United States
Jasmine
The price is €299
includes taxes & fees
9 Nov - 10 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A wooden house with a stone pathway leading to a wooden deck.

4. Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Greenwich
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is €1,435
includes taxes & fees
20 Oct - 21 Oct
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
A blue house with a porch, an American flag, and a brick pathway leading to the entrance.

5. Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
The price is €623
includes taxes & fees
22 Oct - 23 Oct
Bright Cornwall-on-hudson Vacation Rental!
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

Hyatt Regency Greenwich

Hyatt Regency Greenwich

8/10 Good
"This hotel wasn’t bad by any means, comfortable and clean, but shouldn’t be designed as a luxury stay. No amenities like in room snacks/mini bar, slippers, etc - not even toilet paper stocked at the front desk if you need extra, and there just wasn’t anything stand out."
Natalie 5-night trip
Posted 11 hours ago
Hyatt Regency Greenwich

Find out more about Ossining

Ossining Cottages information

Number of reviews
172
Accommodation
57 Cottages
Lowest Price
€299
Highest Price
€1,435

Frequently asked questions

Why book your cottage in Ossining with Expedia?
We think that holidays should be a walk in the park, so if you're chasing cottages in Ossining at an affordable price, Expedia can help. Stick to the budget and go for a wallet-friendly option surrounded by wilderness, or splurge on an upmarket cottage to spoil your favourite people.
How can I find cheap cottages in Ossining?
Expedia is here to help you look for cheap cottages in Ossining. To book the perfect stay in just a few clicks, try out the filter tool to refine your search results by budget, amenities and star rating.
What is there to do in Ossining near my cottage?
Ossining has enough experiences to keep you going for weeks, beginning with Sing Sing Correctional Facility. Thomas J. Watson Research Centre, Louis Engel Waterfront Park and Ossining Historical Society are other awesome attractions. If you're lingering longer, Sing Sing Prison Museum and Teatown Lake Reservation will cap off your itinerary nicely.