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Oakham Vacation Rentals

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

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    Our top choices for Oakham vacation homes

    1. Cottage by the Castle – Downtown Spencer

    Outdoor dining

    2. The Christmas Cottage, 4BR New England Escape

    A bedroom with a four-poster bed, wooden flooring, a dresser, a television, and a window with curtains.

    3. Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

    A house with a red roof, a wooden deck, and a well-maintained lawn.

    4. Angel Sky Challenge

    A two-story house with a central entrance, a brick foundation, and a large front yard.

    5. Worcester Lakefront Cottage Apt w/ Shared Dock!

    A wooden deck with outdoor furniture, a white railing, and a view of a lake.

    6. 4-bedroom house in nice Holden with WiFi, AC

    A spacious dining area with a large window, a fireplace, and a dining table set for four.

    7. Spacious 4-bedroom with four and half bathrooms

    A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

    8. Beautiful two-story home close to downtown worcester 5beds-4bedroom

    A wooden deck with a white fence and greenery in the background.

    9. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

    A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

    10. Entire home in Sterling, Massachusetts, United States

    A modern kitchen with a marble island, white cabinetry, and pendant lighting.

    11. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

    A living room with a flat-screen TV mounted on a wooden wall, a red entertainment unit, a grey sofa, and a marble coffee table with a plant.

    12. Cozy & Stylish 2-bedroom Home in Leominster

    A staircase with dark wooden steps and white handrails, leading to a door at the top.

    13. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

    A fire pit with chairs and a table on a brick patio overlooking a lake.

    14. Lake House in Sturbridge w/All the Views!

    A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

    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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    Top reviews in Oakham

    The Inn Crowd Bed and Breakfast

    A two-story house with a dark blue exterior and white trim, a front porch with steps, and a brick pathway leading to the entrance.

    Holiday Inn Express & Suites Sturbridge by IHG

    A hotel lobby with seating areas, a dining area, and a kitchenette.

    Publick House Historic Inn and Country Motor Lodge

    A white colonial-style house with a symmetrical facade, a central entrance, and a well-maintained garden with colorful flowers.

    Holiday Inn Express Hotel & Suites Auburn by IHG

    A hotel with a parking lot, a covered entrance, and a brick facade.

    Hampton Inn & Suites Worcester

    A modern interior with a dark-toned shelving unit displaying books, decorative items, and framed artwork.

    La Quinta Inn by Wyndham Auburn Worcester

    A hotel room with a bed, a desk with a computer, a TV, a microwave, a mini fridge, and a window with blinds.

    Spark By Hilton Northborough

    A hotel room with two beds, a nightstand, a lamp, a painting, and a window with curtains.

    Hampton Inn Auburn

    A hotel room with two beds, a desk, a TV, and a window.

    Scottish Inn Sturbridge

    A large building with multiple windows and a well-maintained garden with various plants and flowers.

    Homewood Suites By Hilton Worcester

    A modern lounge area with a stone wall, a fireplace, and a seating arrangement including sofas and a coffee table.

    Courtyard by Marriott Worcester

    A modern hotel room with a sofa, armchair, ottoman, and a framed picture on the wall.

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