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North Shore Rentals

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Eastern Point on the Sea

Gloucester
4 Bedrooms
2.5 Bathrooms

Eastern Point is known as the place where the elite summered - and now you can too. 4 beds/2 baths, astounding water views, huge yard, and private sandy beach just across the quiet, private road will make you never want to leave.

Barlovento

Gloucester
5 Bedrooms
5.5 Bathrooms

Barlovento, the Spanish name for windward, is also the name of one of Eastern Point's historic vacation rentals.
Steps to Raymonds Beach. It is one of the original cottages on Eastern Point. Built c. 1889, this Tudor style residence seamlessly blends th

Seaside House

Gloucester
4 Bedrooms
2.5 Bathrooms

Waterviews & walk to Good Harbor Beach. This vacation rental home is large and comfortable and is just steps to the white sands and surf of Good Harbor Beach in one direction and the back shore in the other.

Beach Walk

Gloucester
1 Bedroom
1 Bathroom

Step out the door, walk over the footbridge, and find yourself on Good Harbor Beach! Sun, sand, surf -- all in a minute, just outside your door.

Perrywinkle

Gloucester
4 Bedrooms
2.5 Bathrooms

The best of Rocky Neck! Swim from your private beach or tie up your boat to its tidal dock and enjoy the waters of scenic Gloucester Harbor.

High Rock Cottage

Gloucester
6 Bedrooms
4.5 Bathrooms

Astounding views from every angle! Fabulous vacation rental home, situated on the highest point of Brier Neck. A 5-minute walk in either direction will take you to the surf and sands of Good Harbor Beach or Long Beach.

Captain John Stephens House

Gloucester
0.5 Bedrooms
1 Bathroom

Beautiful studio with a gorgeous eat-in granite kitchen, radiant floor heat, brand-new appliances, outdoor space and parking. The unit may be booked by the week in the summer (June-Sept), and has a two week minimum booking for the rest of the year.

Bell View

Gloucester
6 Bedrooms
5.5 Bathrooms

This spacious and gracious vacation home can sleep up to 16 people, making it the perfect vacation getaway for your extended family. Complete with a large lawn, air conditioning and a tennis court.

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