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Winter Rentals

Looking for house rentals in Massachusetts during the year? The off-season is a great time to enjoy Cape Ann and Boston’s North Shore. Atlantic Vacation Homes has many vacation rental homes that are available on a weekly or monthly basis between September and June at reduced rates. Find winter rentals in Gloucester MA, Rockport MA and beyond.

Check our featured Winter Rentals list below to submit an inquiry online or call our office at (855) 853-9143. For longer term & year round rentals, check our Long Term Rentals page.

  • Winter Rentals Gloucester MA
    High Rock Cottage Apartment
    Gloucester MA Winter Rental
    1 Bedroom
    1 Bathroom
    Sleeps 2
    $1400/mo, inclusive
    Avail. 10/1/19

     

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  • Winter Rentals Gloucester MA
    Harbor's Corner
    Gloucester MA Winter Rental
    2 Bedrooms
    1.5 Bathrooms
    Sleeps 4
    $1500/mo, plus utilities
    Avail. immediately

     

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  • Gloucester MA Winter Rentals
    Annisquam River Sunsets
    Gloucester MA Winter Rental
    2 Bedrooms
    1 Bathroom
    Sleeps 4
    $1700/mo, utilities included
    Avail. immediately

     


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  • Winter Rentals Gloucester MA
    Rocky Neck Lookout
    Gloucester MA Winter Rental
    2 Bedrooms
    1 Bathrooms
    Sleeps 4
    $1800/mo utilities included
    Avail. immediately

     

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  • Winter Rentals Rockport MA
    Rockport Seaside Retreat
    Rockport MA Winter Rental
    4 Bedrooms
    2 Bathrooms
    Sleeps 7
    $1800/mo, plus utilities
    Avail. immediately

     

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  • Winter Rentals Rockport MA
    The View on Bearskin Neck
    Rockport MA Winter Rental
    1 Bedrooms
    1 Bathroom
    Sleeps 2
    $1800/mo, utilities included
    Avail. immediately

     

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  • Winter Rentals Gloucester MA
    Boulevard Bungalow
    Gloucester MA Winter Rental
    3 Bedrooms
    2 Bathrooms
    Sleeps 6
    $1900/mo, plus utilities
    Avail. 10/1/19

     

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  • Winter Rentals Gloucester MA
    Helena House
    Gloucester MA Winter Rental
    3 Bedrooms
    3 Bathrooms
    Sleeps 7
    $1900/mo, plus utilities
    Avail. 11/1/19

     

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  • Winter Rentals Gloucester MA
    Parker House
    Gloucester MA Winter Rental
    4 Bedrooms
    2 Bathrooms
    Sleeps 4
    $1900/mo, plus utilities
    Avail. immediately

     

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  • Pet Friendly Gloucester MA Winter Rentals
    Glitter Bay
    Gloucester MA Winter Rental
    3 Bedrooms
    1.5 Bathrooms
    Sleeps 5
    $1950/mo, plus utilities
    Avail. immediately

     

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  • Winter Rentals Gloucester MA
    Rockport Hideaway
    Rockport MA Winter Rental
    3 Bedrooms
    2 Bathrooms
    Sleeps 6
    $2000/mo, plus utilities
    Avail. immediately

     

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  • Winter Rentals Rockport MA
    Tuller House
    Rockport MA Winter Rental
    3 Bedrooms
    1 Bathroom
    Sleeps 5
    $2000/mo, plus utilities
    Avail. immediately

     

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  • Winter Rentals Gloucester MA
    West Wind
    Gloucester MA Winter Rental
    4 Bedrooms
    2 Bathrooms
    Sleeps 8
    $2100/mo, plus utilities
    Avail. immediately

     

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  • Winter Rentals Gloucester MA
    Rocky Neck Hilltop
    Gloucester MA Winter Rental
    2 Bedrooms
    2 Bathrooms
    Sleeps 4
    $2200/mo, plus utilities
    Avail. 10/15/19

     

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  • Gloucester MA Winter Rentals
    Ships Bell
    Gloucester MA Winter Rental
    3 Bedrooms
    2 Bathrooms
    Sleeps 6
    $2200/mo, inclusive
    Avail. 11/1/19

     

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  • Winter Rentals Rockport MA
    The Garden House
    Rockport MA Winter Rental
    3 Bedrooms
    2.5 Bathrooms
    Sleeps 6
    $2300/mo, plus utilities
    Avail. immediately

     

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  • Winter Rentals Rockport MA
    Cambourne Way
    Rockport MA Winter Rental
    3 Bedrooms
    2.5 Bathrooms
    Sleeps 7
    $2500/mo, plus utilities
    Avail. immediately

     

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  • Winter Rentals Gloucester MA
    Sunset Cove
    Gloucester MA Winter Rental
    2 Bedrooms
    2.5 Bathrooms
    Sleeps 6
    $2500/mo, plus utilities
    Avail. 1/1/20

     

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  • Winter Rentals Gloucester MA
    Perrywinkle
    Gloucester MA Winter Rental
    4 Bedrooms
    2 Bathrooms
    Sleeps 7
    $2500/mo, heat & electricity included
    Avail. immediately

     

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  • Winter Rentals Rockport MA
    The Rockporter
    Rockport MA Winter Rental
    4 Bedrooms
    2 Bathrooms
    Sleeps 5
    $2500/mo, inclusive
    Avail. 1/1/20

     

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  • Winter Rentals Gloucester MA
    Over By Good Harbor
    Gloucester MA Winter Rental
    3 Bedrooms
    2.5 Bathrooms
    Sleeps 8
    $3000/mo, plus utilities
    Avail. 12/3/19

     

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  • Pet-Friendly Winter Rentals Gloucester MA
    Beach Stone Cottage
    Gloucester MA Winter Rental
    3 Bedrooms
    2 Bathrooms
    Sleeps 6
    $3400/mo, inclusive
    Avail. 12/1/19

     

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  • Gloucester MA Winter Beach Rentals
    Salt Island Views
    Gloucester MA Winter Rental
    3 Bedrooms
    2 Bathrooms
    Sleeps 8
    $3800/mo, inclusive
    Avail. 10/1/19  

     

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