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North Shore Rentals

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Thurston Point Cottage

Gloucester
3 Bedrooms
1.5 Bathrooms

This sweet and comfortable waterfront cottage with spectacular sunset views over the Annisquam River offers a wonderful New England retreat. Swim and kayak from the property or fish off the new deepwater dock and enjoy the offerings of the garden.

River Breezes Cottage

Gloucester
3 Bedrooms
3.5 Bathrooms

Views of the sparkling waters of the Annisquam River, Ipswich Bay, Wingaersheek Beach and the Annisqaum Yacht Club just across the river. Incredible sunsets await you every evening! Monthly rates available in winter.

Little Red House

Gloucester
3 Bedrooms
1 Bathroom

Enjoy this comfortable vacation home just steps away from Gloucester's historic Stage Fort Park, which was once a landing place for pirates, but is now a beachside venue for free concerts, fireworks and so mucn more.

Helena House

Gloucester
3 Bedrooms
1.5 Bathrooms

This delightful Queen Anne-style vacation rental home is bright and cheery and just waiting for you! Walk to Plum Cove Beach (0.7 miles).

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.

Sunset Cottage

Gloucester
2 Bedrooms
1 Bathroom

Named for the glorious sunsets to be seen every evening from your choice of two waterfront decks this delightful 2 bedroom/1 bath cottage could not be any closer to the crystal waters of the tidal, Annisquam River!

Golden Sands

Gloucester
7 Bedrooms
3.5 Bathrooms

Golden Sands is the quintessential turn of the century Gloucester beach "cottage." With views of Good Harbor Beach, the twin lighthouses of Rockport and the scenic Atlantic Ocean from its wrap around porch and decks, you will never want to leave!

Garden by the Sea

Gloucester
2 Bedrooms
1 Bathroom

Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach and Thatcher Island from this bright and delightfully furnished two bedroom vacation rental.

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.

Ships Bell House

Gloucester
3 Bedrooms
2 Bathrooms

Have it all at Ships Bell House, an immaculate vacation rental home with amazing water views. An added bonus of a fresh water swimming quarry is just steps away. Walk to a sandy beach or to the quaint village of Lanesville.

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