A wooden boardwalk winding through a forest with autumn foliage.

Search Ossining Cottages

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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 £616
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, (25 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is £327
includes taxes & fees
15 Oct - 16 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, (148 reviews)
"We had a great stay!!"
United States
Jasmine
The price is £257
includes taxes & fees
20 Oct - 21 Oct
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 £1,212
includes taxes & fees
13 Oct - 14 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 £528
includes taxes & fees
22 Oct - 23 Oct
Bright Cornwall-on-hudson Vacation Rental!
A wooden deck with a railing overlooking a well-maintained lawn and trees.

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

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
9.6 out of 10, Exceptional, (10 reviews)
"lovely porch and backyard."
United States
Kaia W.
The price is £832
includes taxes & fees
4 Nov - 5 Nov
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.
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

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

10/10 Excellent
"First time in ny so didn’t know what to expect but room was clean staff was nice"
Emilee 4-night trip
Posted less than an hour ago
LIV Hotel Bronx - Newly Built

Find out more about Ossining

Ossining Cottages information

Number of reviews
184
Accommodation
55 Cottages
Lowest Price
£257
Highest Price
£1,212

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.