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.
Brooks Lane
Gloucester MA Winter Rental
Studio
1 Bathrooms
Sleeps 2
$1200/mo, inc. heat
Avail. immediatelyLearn More 
Boulevard Bungalow
Gloucester MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 6
$1900/mo, plus utilities
Avail. 10/1/19Learn More 
Tuller House
Rockport MA Winter Rental
3 Bedrooms
1 Bathroom
Sleeps 5
$2000/mo, plus utilities
Avail. immediatelyLearn More 
Rocky Neck Hilltop
Gloucester MA Winter Rental
2 Bedrooms
2 Bathrooms
Sleeps 4
$2200/mo, plus utilities
Avail. 10/15/19Learn More 
Rockport Seaside Retreat
Rockport MA Winter Rental
4 Bedrooms
2 Bathrooms
Sleeps 7
$2100/mo, plus utilities
Avail. immediatelyLearn More 
Cambourne Way
Rockport MA Winter Rental
3 Bedrooms
2.5 Bathrooms
Sleeps 7
$2500/mo, plus utilities
Avail. immediatelyLearn 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 
Sea Vagabond
Rockport MA Winter Rental
3.5 Bedrooms
2 Bathrooms
Sleeps 8
$1400/mo, plus utilities
Avail. 10/1/19Learn More 
Treehouse by the Sea
Gloucester MA Winter Rental
2 Bedrooms
1.5 Bathrooms
Sleeps 4
$1550/mo, inclusive
Avail. 11/1/19Learn More 
Rockport Hideaway
Rockport MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 6
$2000/mo, plus utilities
Avail. immediatelyLearn More 
Beach Stone Cottage
Gloucester MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 6
$3400/mo, inclusive
Avail. 12/1/19Learn More 
High Rock Cottage Apartment
Gloucester MA Winter Rental
1 Bedroom
1 Bathroom
Sleeps 2
$1400/mo, inclusive
Avail. 10/1/19Learn More 
Granite Pier
Rockport MA Winter Rental
3 Bedrooms
1.5 Bathrooms
Sleeps 8
$3300/mo, plus utilities
Avail. immediatelyLearn More 
Perrywinkle
Gloucester MA Winter Rental
4 Bedrooms
2.5 Bathrooms
Sleeps 6
$3000/mo, plus utilities
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Salt Island Views
Gloucester MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 8
$3800/mo, inclusive
Avail. 10/1/19Learn More 
Ships Bell
Gloucester MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 6
$2500/mo, inclusive
Avail. 11/1/19Learn More 
The Robert House
Rockport MA Winter Rental
4 Bedrooms
1 Bathrooms
Sleeps 7Learn More 
Todd Cottage
Rockport MA Winter Rental
2 Bedrooms
1.5 Bathrooms
Sleeps 4
$1650/mo, plus utilities
Avail. 10/1/19Learn More 
Glitter Bay
Gloucester MA Winter Rental
3 Bedrooms
1.5 Bathrooms
Sleeps 5
$2100/mo, plus utilities
Avail. 10/1/19Learn More 
The Rockporter
Rockport MA Winter Rental
4 Bedrooms
2 Bathrooms
Sleeps 5
$2500/mo, inclusive
Avail. 1/1/20Learn More 
Landfall
Rockport MA Winter Rental
5 Bedrooms
3 Bathrooms
Sleeps 10Learn More 
Helen's Way
Gloucester MA Winter Rental
1 Bedroom
1 Bathroom
Sleeps 4Learn More 
Squam Cottage
Gloucester MA Winter Rental
3 Bedrooms
2 Bathrooms
Sleeps 7
$2000/mo, plus utilities
Avail. 10/15/19Learn More 
Helena House
Gloucester MA Winter Rental
3 Bedrooms
3 Bathrooms
Sleeps 7
$1900/mo, plus utilities
Avail. 11/1/19Learn More 
Harbor's Corner
Gloucester MA Winter Rental
2 Bedrooms
1.5 Bathrooms
Sleeps 4
$1500/mo, plus utilities
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Sunset Cove
Gloucester MA Winter Rental
2 Bedrooms
2.5 Bathrooms
Sleeps 6
$2500/mo, plus utilities
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Chester Square
Gloucester MA Winter Rental
3 Bedrooms
3 Bathrooms
Sleeps 6
$2650/mo, plus utilities
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The Garden House
Rockport MA Winter Rental
3 Bedrooms
2.5 Bathrooms
Sleeps 6
$2300/mo, plus utilities
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Parker House
Gloucester MA Winter Rental
4 Bedrooms
2 Bathrooms
Sleeps 4
$2500/mo, plus utilities
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West Wind
Gloucester MA Winter Rental
4 Bedrooms
2 Bathrooms
Sleeps 8
$2500/mo, plus utilities
Avail. immediatelyLearn More
