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A church interior with wooden pews, a central aisle, and a stained glass window.

Photo by Jules & Jenny (Creative Commons Attribution 2.0)

Search Guest Houses in Uppingham from CA $60

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    Check prices for these dates, December 15–16, 2026

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    Our top choices for Uppingham guest houses

    1. Oakham hotel

    A dining area with a stone wall, a fireplace, and a table set for four.

    2. Contractor Accommodation - Cacco

    A corridor with a wooden slat wall, a grey carpeted floor, and a white door at the end.

    3. Nice Living Serviced Accommodations Leicester 2

    A bedroom with two beds, a desk, and a chair.

    4. The City Rooms

    A historic building with arched windows and a central entrance, surrounded by a black iron fence.

    5. Glenfield Lodge Guest House

    A hallway with a brick wall and a large poster of a street scene.

    6. Abinger Guest House

    A bedroom with a bed, a TV mounted on the wall, a wooden cabinet, a small table with a coffee maker, and a bathroom with a sink and mirror.

    7. Campbell's Guest House

    A hotel room with two beds, a desk, a chair, a standing fan, and large windows with curtains.

    8. The Bell Gate House

    A room with a checkered wooden wall, a glass table, and two potted plants.

    9. The Woolpack Inn Islip

    A stone building with a sign for 'The New Inn' and 'En-Suite Accommodation'.

    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 Uppingham

    These charming market towns showcase historic architecture with Uppingham's antique shops and Oakham's impressive castle featuring a unique collection of ceremonial horseshoes. Explore the quaint independent boutiques and tea rooms, then visit nearby Rutland Water for sailing, cycling, and spotting ospreys at the nature reserve.

    See all hotels in Uppingham

    A church interior with wooden pews, a central aisle, and a stained glass window.

    Photo by Jules & Jenny