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Search Guest Houses in Chester

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

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    Our top choices for Chester guest houses

    1. The Central Downtown Inn & Suites

    A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

    2. Hideaway Inn Lenox

    A large white house with a prominent tower, surrounded by lush greenery and a well-maintained lawn.

    3. Berkshire Village Carriage House - Super Private!!

    A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

    4. A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

    A stone cottage with a turquoise door, a sign reading 'Windy Top Cottage,' and flower boxes on the windows.

    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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