Plan your trip

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

Search Winchester Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

  • Find vacation rentals that suit your style

    Cabins

    Apartments

    Cottages

    Chalets

    Condos

    Check prices for these dates

    Check prices for these dates, December 13 – 14, 2026

    View in a map

    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.

    View all properties

    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.

    Windmill Motel Restaurant

    A windmill, a row of cabins, and a forest backdrop.

    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.

    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.

    Inn on Putney Road

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

    Hampton Inn & Suites Keene

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

    Keene Elm City Hotel, an Ascend Collection Hotel

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

    The Carriage Barn Inn

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

    Comfort Inn & Suites Brattleboro I-91

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

    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.

    Latchis Hotel

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

    Chesterfield Inn

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

    Courtyard by Marriott Keene Downtown

    A multi-story brick building with a sign reading "COURTYARD BY MARRIOTT".

    Hampton Inn Brattleboro

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

    Colonel Williams Inn

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

    Deerfield Inn

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

    Explore a world of travel with Expedia