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Gloucester, MA Houses for Rent

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    $3,100 per month

    • 4 Beds
    • 2.5 Baths
    • 1,893 Sq Ft
    • House for Rent

    11 Sleepy Hollow Rd, Gloucester, MA 01930

    Seasonal furnished rental available September 1, 2025 through May 1, 2026 (date could be flexible). This home offers a living room with a fireplace which is open to the kitchen and the dining room (area). The kitchen door leads to a beautiful deck over looking the yard. The first floor also has the main bedroom with a half bathroom attached and one additional bedroom and a full bath. The

    Stephanie Moio J. Barrett & Company

    11 Sleepy Hollow Rd, Gloucester, MA 01930
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    $8,000 per month

    • 5 Beds
    • 3 Baths
    • 2,343 Sq Ft
    • House for Rent

    18 Rear Bungalow Rd, Gloucester, MA 01930

    --SHORT TERM RENTAL -- Price is a base price and per week. Inquire for longer stays. Private oceanfront Wingaersheek Beach house features five bedrooms, three bathrooms and has recently been renovated with custom steel front double doors, new wood floors, pine interior paneled walls, new kitchen cabinets, counters, bathrooms, and mini split AC units. The house spans three levels along with an

    Stephen Sassoon Sassoon Group, LLC

    18 Rear Bungalow Rd, Gloucester, MA 01930
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    $40,000 per month

    • 5 Beds
    • 2 Baths
    • 3,300 Sq Ft
    • House for Rent

    62 Crafts Rd, Gloucester, MA 01930

    Modern Cape Ann coastal retreat. Sitting on 1.4 waterfront acres with granite outcroppings, mature trees, and gardens. Private deepwater dock, 5 feet at low tide, accommodates 2-3 boats. Riverfront peninsula with sweeping water and marsh views, perfectly located in the middle of the Annisquam River. Take trips out to Ipswich Bay, the bustling Gloucester Harbor and open waters beyond. Features

    John & Cindy Farrell Coldwell Banker Realty - Beverly

    62 Crafts Rd, Gloucester, MA 01930
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    $7,000 per month

    • 4 Beds
    • 4 Baths
    • 3,567 Sq Ft
    • House for Rent

    39 Decatur St, Gloucester, MA 01930

    WEEKLY SUMMER RENTAL in spacious, well-appointed family home on privately situated, green leafy lot, yet less than half a mile away from the Good Harbor Beach Footbridge. With Bass Rocks Golf Club and tennis courts around the corner and Rocky Neck and downtown Gloucester a short distance away, this is a prime location for fun with friends and family. Generous kitchen opens to family room with

    Amanda Armstrong Compass

    39 Decatur St, Gloucester, MA 01930
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    $3,200 per month

    • 3 Beds
    • 1.5 Baths
    • 2,480 Sq Ft
    • House for Rent

    58 Sumner St, Gloucester, MA 01930

    Welcome to Major John Burnham’s historic 17th-century home, a rare opportunity to rent a stately and distinguished property rich in history. This West Gloucester gem showcases original King Pine wood floors, raised paneled walls, exposed beams, and multiple decorative fireplaces, preserving its authentic colonial charm. Enjoy the enclosed three season sunroom, inviting fresh air and tranquil

    Crowell & Frost Realty Group J. Barrett & Company

    58 Sumner St, Gloucester, MA 01930
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    $4,850 per month

    • 3 Beds
    • 2.5 Baths
    • 1,776 Sq Ft
    • House for Rent

    3 Fort Hill Ave, Gloucester, MA 01930

    WINTER RENTAL on Easten Point. This carriage house is available until April 30, 2025. This new home is fully furnished and outfitted for luxe living in a serene setting. Open concept first floor is chic and comfortable. Three well appointed bedrooms and two baths upstairs with a half bath on the first floor. Deluxe outdoor kitchen, This home is ideal for a winter retreat, a place to call home

    Scott Smith Coldwell Banker Realty - Manchester

    3 Fort Hill Ave, Gloucester, MA 01930
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    $9,000 per month

    • 4 Beds
    • 3 Baths
    • 2,164 Sq Ft
    • House for Rent

    1 Sandy Way, Gloucester, MA 01930

    Wingaersheek Coffin's Beach One Week Summer Rental !! Available 8/20 through 8/27/2025 Coastal living at its finest in this fully furnished home, offers a large open floor plan. First floor has kitchen, living room, dining room, one bedroom, full bath and den. Double sliders allow access to the outside deck. Second floor has a large main bedroom with full bath, two bedrooms and a shared bath. The

    Christine Grammas J. Barrett & Company

    1 Sandy Way, Gloucester, MA 01930
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    $4,500 per month

    • 4 Beds
    • 3.5 Baths
    • 2,900 Sq Ft
    • House for Rent

    17 Fort Hill Ave, Gloucester, MA 01930

    WINTER SEASONAL RENTAL - Flexible lease/price options considered. Charming English Tudor Carriage House privately located in the heart of Eastern Point within walking distance of two sandy beaches, DogBar Breakwater, Eastern Point Light House and many nature paths; only a 10 minute drive to Rt. 128 and all things Gloucester. Only minutes from Rocky Neck Art Colony and Gloucester Stage Company.

    Lois Budrose Advisors Living - Gloucester

    17 Fort Hill Ave, Gloucester, MA 01930
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    $6,500 per month

    • 7 Beds
    • 3.5 Baths
    • 4,267 Sq Ft
    • House for Rent

    24 Wonson St, Gloucester, MA 01930

    Escape to this beautiful Home nestled in the heart of Rocky Neck, a destination that promises to lure you back time & again. Ideal for hosting lg. wedding parties or cherished family reunions. This home boasts newly renovated interiors adorned w/ exquisite finishes & tasteful furnishings. A true haven for vacationers, it features ample outdoor entertainment areas, including outdoor fire pits, a

    Charleen McCarthy Five Mark Realty Group LLC

    24 Wonson St, Gloucester, MA 01930
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    $20,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,518 Sq Ft
    • House for Rent

    14 Sunset Point Rd, Gloucester, MA 01930

    OCEANFRONT IN LANESVILLE SUMMER RENTAL WITH DATES STILL AVAILABLE STARTING IN MID-AUGUST. Idyllic summer retreat in stunning and private oceanfront setting in one of the North Shore’s most scenic communities. This is the perfect base for exploring the many delights of Lanesville, from its rugged shoreline to colorful Lanesville village with its studios and cafes. Head to beautiful Lane’s Cove,

    Amanda Armstrong Compass

    14 Sunset Point Rd, Gloucester, MA 01930
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