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A white church with a steeple and clock tower, surrounded by trees and a well-maintained lawn.

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    Check prices for these dates, 14 – 15 December 2026

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    Our top choices for Sterling holiday homes

    1. Entire home in Sterling, Massachusetts, United States

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

    2. Cozy & Stylish 2-bedroom Home in Leominster

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

    3. Angel Sky Challenge

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

    4. Worcester Lakefront Cottage Apt w/ Shared Dock!

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

    5. 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.

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

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

    8. 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.

    9. Cottage by the Castle – Downtown Spencer

    Outdoor dining

    10. Spacious 4-bedroom with four and half bathrooms

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

    11. Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

    A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

    12. Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston

    A modern kitchen with white cabinets, a central island with bar stools, a large window, and a dark ceiling beam.

    13. Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!

    A spacious living room with wooden beams, a sliding glass door to a patio, and a cozy seating area with a sofa and chairs.

    14. Enjoy your stay in an antique home in an antique toy museum!

    A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

    15. A Quintessential New England Historical Guesthouse

    A kitchen with a marble countertop, stainless steel appliances, and wooden beams.

    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 Sterling

    Families flock to Davis' Farmland & Mega Maze where children can pet farm animals and parents can navigate the challenging corn labyrinth. History buffs shouldn't miss the charming Mary Had a Little Lamb Statue, while nature lovers can explore nearby Tower Hill Botanic Garden's stunning seasonal displays.

    See all hotels in Sterling

    A white church with a steeple and clock tower, surrounded by trees and a well-maintained lawn.

    Top reviews in Sterling

    Homewood Suites by Hilton Marlborough

    A spacious lobby with a curved sofa, two armchairs, a glass coffee table, and a stone fireplace.

    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 Hotel & Suites Boston-Marlboro by IHG

    A modern dining area with multiple tables and chairs, a flat-screen TV mounted on the wall, and large windows providing natural light.

    Embassy Suites by Hilton Boston Marlborough

    A modern restaurant with a central bar, wooden paneling, and a high ceiling with skylights.

    Spark By Hilton Northborough

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

    Residence Inn by Marriott Boston Marlborough

    A spacious lobby with a stone fireplace, seating areas, and a modern design.

    Hampton Inn Boston/Marlborough

    An indoor swimming pool with clear blue water, surrounded by bright yellow and green chairs and tables, and large windows offering a view of the outdoors.

    Hyatt Place Marlborough/Apex Center

    A multi-story hotel with a prominent "Hyatt Place" sign, a covered entrance, and a parking lot.

    SpringHill Suites by Marriott Boston Devens Common Center

    A modern kitchen with a buffet setup, including a stove, food display, and various appliances.

    Hilton Garden Inn Devens Common

    A hotel room with a large window, a round table, and four patterned chairs.

    AC Hotel by Marriott Worcester

    A modern living room with a fireplace, comfortable seating, and a large window.