Ossining Cottages

A wooden boardwalk winding through a forest with autumn foliage.

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Our top choices for Ossining cottages

A wooden deck with a railing overlooking a body of water and trees.

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

Croton-on-Hudson

Eva C.

includes taxes & fees

27 Sept - 28 Sept

A house with a view of a bridge and mountains.

2. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery

Jasmine

includes taxes & fees

29 Sept - 30 Sept

A two-story house with a wooden exterior, a front porch, and a staircase leading to the entrance.

3. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Putnam Valley

Heather T.

includes taxes & fees

28 Sept - 29 Sept

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

Greenwich

Lisa H.

includes taxes & fees

26 Sept - 27 Sept

A blue house with a porch, an American flag, and a brick pathway leading to the entrance.

5. Bright Cornwall-on-hudson Vacation Rental!

Cornwall

Poyuk

includes taxes & fees

22 Oct - 23 Oct

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Top Ossining Hotel Reviews

Royal Regency Hotel

8/10 Good

"The staff was great. the bed was super uncomfortable other than that, not a bad property"

Windrose On Hudson

10/10 Excellent

"The hotel was lovely. It must have been a truly impressive estate back in the day. The public spaces are renovated so beautifully. The room had so much natural light with the floor to ceiling windows, the beds were quite comfortable and the bathroom had everything we needed. I just wish I could have spent a few more days there!"

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