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A snow-covered bridge over a river with a red roof, surrounded by trees and buildings.

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    Check prices for these dates, December 14 – 15, 2026

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    Our top choices for Winchester cottages

    1. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

    A house by a lake with a dock and a boat.

    2. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

    A wooden deck with two chairs and a table, overlooking a lake with trees in the background.

    3. Cozy Tiny House on Main Street. Fully Renovated.

    A small, single-story building with a front door and a small window.

    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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    Learn more about Winchester

    Hike the scenic trails of Pisgah State Park where rangers know which routes offer the best wildlife viewing. Explore the historic downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

    See all hotels in Winchester

    A snow-covered bridge over a river with a red roof, surrounded by trees and buildings.

    Top reviews in Winchester

    Centennial House

    A two-story house with a red door, green shutters, and a snow-covered front yard.

    The Inn At Crumpin Fox

    A brick building with a red awning and a sign that reads "The Inn."

    Riverside Hotel, an Ascend Collection Hotel

    A dock extending into a lake with a grassy area in the foreground and trees in the background.

    Vikings Villages Resort

    A wooden cabin with a thatched roof, accessible via a wooden walkway with railings.

    Holiday Inn Express Hotel & Suites Brattleboro by IHG

    A hotel with a covered entrance, a clear sky, and a tree in the foreground.

    Latchis Hotel

    A multi-story building with a prominent sign for 'Hotel Latchis' indicating it houses a coffee shop, theater, and ballroom.

    The Carriage Barn Inn

    A two-story building with a porch, a sign indicating guest rooms, and an American flag.

    Keene Elm City Hotel, an Ascend Collection Hotel

    The exterior of the Keene Elm City Hotel with a parking lot in front.

    Hampton Inn & Suites Keene

    A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.

    Comfort Inn & Suites Brattleboro I-91

    A multi-story hotel with a stone facade and a flat roof.

    Inn on Putney Road

    A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

    Best Western Plus Keene Hotel

    A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

    Hampton Inn Brattleboro

    A large, yellow building with a sign for Hampton Inn. There are cars parked in front and a clear sky.

    Chesterfield Inn

    A large, two-story house with a snow-covered driveway and surrounding trees.

    Deerfield Inn

    A historic building with a covered porch, American flags, and a sign reading 'Deerfield Inn.'

    Otherland Hotel

    A triangular wooden structure with a bench and a table, surrounded by lush greenery and a building in the background.

    Colonel Williams Inn

    A well-maintained lawn with a large tree and a stone wall.

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