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.
High Rock Cottage Apartment
Gloucester MA Winter Rental
1 Bedroom
1 Bathroom
Sleeps 2
$1400/mo, inclusive
Avail. 10/1/19Learn More 
Harbor's Corner
Gloucester MA Winter Rental
2 Bedrooms
1.5 Bathrooms
Sleeps 4
$1500/mo, plus utilities
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Annisquam River Sunsets
Gloucester MA Winter Rental
2 Bedrooms
1 Bathroom
Sleeps 4
$1700/mo, utilities included
Avail. immediately
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Rocky Neck Lookout
Gloucester MA Winter Rental
2 Bedrooms
1 Bathrooms
Sleeps 4
$1800/mo utilities included
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Rockport Seaside Retreat
Rockport MA Winter Rental
4 Bedrooms
2 Bathrooms
Sleeps 7
$1800/mo, plus utilities
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The View on Bearskin Neck
Rockport MA Winter Rental
1 Bedrooms
1 Bathroom
Sleeps 2
$1800/mo, utilities included
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Boulevard Bungalow
Gloucester MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 6
$1900/mo, plus utilities
Avail. 10/1/19Learn More 
Helena House
Gloucester MA Winter Rental
3 Bedrooms
3 Bathrooms
Sleeps 7
$1900/mo, plus utilities
Avail. 11/1/19Learn More 
Parker House
Gloucester MA Winter Rental
4 Bedrooms
2 Bathrooms
Sleeps 4
$1900/mo, plus utilities
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Glitter Bay
Gloucester MA Winter Rental
3 Bedrooms
1.5 Bathrooms
Sleeps 5
$1950/mo, plus utilities
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Rockport Hideaway
Rockport MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 6
$2000/mo, plus utilities
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Tuller House
Rockport MA Winter Rental
3 Bedrooms
1 Bathroom
Sleeps 5
$2000/mo, plus utilities
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West Wind
Gloucester MA Winter Rental
4 Bedrooms
2 Bathrooms
Sleeps 8
$2100/mo, plus utilities
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Rocky Neck Hilltop
Gloucester MA Winter Rental
2 Bedrooms
2 Bathrooms
Sleeps 4
$2200/mo, plus utilities
Avail. 10/15/19Learn More 
Ships Bell
Gloucester MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 6
$2200/mo, inclusive
Avail. 11/1/19Learn More 
The Garden House
Rockport MA Winter Rental
3 Bedrooms
2.5 Bathrooms
Sleeps 6
$2300/mo, plus utilities
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Cambourne Way
Rockport MA Winter Rental
3 Bedrooms
2.5 Bathrooms
Sleeps 7
$2500/mo, plus utilities
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Sunset Cove
Gloucester MA Winter Rental
2 Bedrooms
2.5 Bathrooms
Sleeps 6
$2500/mo, plus utilities
Avail. 1/1/20Learn More 
Perrywinkle
Gloucester MA Winter Rental
4 Bedrooms
2 Bathrooms
Sleeps 7
$2500/mo, heat & electricity included
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The Rockporter
Rockport MA Winter Rental
4 Bedrooms
2 Bathrooms
Sleeps 5
$2500/mo, inclusive
Avail. 1/1/20Learn More 
Over By Good Harbor
Gloucester MA Winter Rental
3 Bedrooms
2.5 Bathrooms
Sleeps 8
$3000/mo, plus utilities
Avail. 12/3/19Learn More 
Beach Stone Cottage
Gloucester MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 6
$3400/mo, inclusive
Avail. 12/1/19Learn More 
Salt Island Views
Gloucester MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 8
$3800/mo, inclusive
Avail. 10/1/19Learn More
