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.
The Cottage at Front Beach
Rockport MA Winter Rental
2 Bedrooms
1.5 Bathrooms
Sleeps 4
$2,500 /mo plus utilities
Avail. 10/1/21Learn More 
Lady Bug House
Rockport MA Winter Rental
2 Bedrooms
1 Bathroom
Sleeps 4
$1,900/mo, plus utilities
Avail. 10/1/21
Learn More
Annisquam River Sunsets
Gloucester MA Winter Rental
2 Bedrooms
1 Bathroom
Sleeps 4
$2,300/mo, including utilities
Available 10/1/21
Learn More
Todd Cottage
Rockport MA Winter Rental
2 Bedrooms
1.5 Bathrooms
Sleeps 4
$2,000/mo, plus utilities
Avail. 10/1/21Learn More -
Changes in Latitude
Gloucester MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 6
$2,500/mo, plus utilities
Available 10/1/21
Learn More 
The John Butman House
Rockport MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 6
$2,750/mo, plus utilities
Avail. 10/1/21Learn More 
Helena House
Gloucester MA Winter Rental
3 Bedrooms
1.5 Bathrooms
Sleeps 7
$2,200/mo, plus utilities
Available 10/15/21Learn More 
Ships Bell
Gloucester MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 6
$2,850/mo, plus utilities
Avail. 1/1/22Learn More 
Chester Square
Gloucester MA Winter Rental
4 Bedrooms
3 Bathrooms
Sleeps 8
$3200/mo, plus utilities
10/1/21Learn More 
Landmark Lookout
Rockport MA Winter Rental
4 Bedrooms
3 Bathrooms
Sleeps 8
$3,500/mo, including utilities
Avail. 10/25/21Learn More