Fort Montgomery Guest Houses from CA $389

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Our top choices for Fort Montgomery guest houses

An aerial view of a campus with multiple buildings, a central courtyard, and a lake in the background.

1. Near NYC! | Stylish Guestroom

Ossining

CA $449 total

includes taxes & fees

Nov 15 - Nov 16

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Learn more about Fort Montgomery

Hike the scenic trails of Fort Montgomery Historic Site where Revolutionary War history comes alive through preserved ruins and engaging exhibits. Bear Mountain State Park nearby offers panoramic Hudson River views, family-friendly picnic areas, and a charming carousel for weekend adventures.

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A person sitting on a concrete bench overlooking a river and hills.

Top reviews in Fort Montgomery

A Holiday Inn Express & Suites sign with a bench and flower beds in front.

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Peekskill

10/10 Excellent

Blair

A hotel with a parking lot, a swimming pool, and a view of a lake and mountains.

West Point Motel

Highland Falls

10/10 Excellent

Anonymous traveller

A hotel entrance with stone pillars, a covered walkway, and a bench.

Sleep Inn & Suites Monroe - Woodbury

Monroe

10/10 Excellent

Helene

A hotel room with two beds, a wooden desk, a television, and a dining area.

FairBridge Inn & Suites at West Point

Highland Falls

10/10 Excellent

Mario

A brick building with a covered patio area featuring outdoor seating and string lights.

Cromwell Manor Inn

Cornwall

10/10 Excellent

Cromwell Manor Inn is a beautiful converted mansion built in the 1760s in upstate New York. Right across from summer camps and nature walks, the peaceful natural environment is like having a front row seat to a nature show. The grounds are beautiful, with mature trees, soft grass, and beautiful flowers. It is like something out of a historical painting. During our stay, we were hosted in a blue guest house just at the entrance of the drive. I imagine it must have been the caretaker's residence...

Cynthia Louise

A Simon Premium Outlet sign at Woodbury Commons.

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

10/10 Excellent

Alex

A view from a covered porch overlooking a lake, with a white fence and trees in the foreground.

Inn on the Hudson

Peekskill

10/10 Excellent

Mario

A spacious lobby with a high ceiling, a reception desk, a seating area with blue sofas and armchairs, and a visible Pepsi refrigerator.

Comfort Suites Fishkill near Interstate 84

Fishkill

10/10 Excellent

Steeve

A large, two-story white house with a wrap-around porch and a small front garden.

The Dominion House Bed & Breakfast

Chester

10/10 Excellent

I’m torn between telling everyone about Dominion House and keeping it to myself. What a glorious B&B, with a swimming pool too. Only 3 rooms so you never feel crowded. Kathy was a welcome host and Liane’s breakfasts were amazing. It was really hot over the weekend, but the house was cool so even though it has A/C, I was still able to sleep with the windows open. So quiet and still. A family of deer wandered the lawn. The bed was comfortable, the water pressure was great, the library had tons of...

Susan