A wooden boardwalk winding through a forest with autumn foliage.

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Check prices for these dates

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

Our top choices for Ossining cottages

Property grounds

1. 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 €287
includes taxes & fees
27 Aug - 28 Aug
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior

2. 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 €415
includes taxes & fees
31 Aug - 1 Sept
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Property grounds

3. 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, (10 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is €1,259
includes taxes & fees
23 Sept - 24 Sept
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Property grounds

4. Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
The price is €840
includes taxes & fees
27 Aug - 28 Aug
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
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

Ramada by Wyndham Bronx

Ramada by Wyndham Bronx

8/10 Good
"It was ok but not worth the price"
Linda 2-night trip
Posted 3 hours ago
Ramada by Wyndham Bronx

Find out more about Ossining

Ossining Cottages information

Number of reviews
182
Accommodation
57 Cottages
Lowest Price
€287
Highest Price
€1,259

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.