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North Shore Rentals

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Treehouse by the Sea

Gloucester
2 Bedrooms
1.5 Bathrooms

Enjoy views, breezes and scent of the sea from this lofty perch overlooking Gloucester's waterfront Boulevard and the iconic "Gloucester Fisherman at the Wheel" sculpture. Weekly in the summer. Monthly rates available in winter.

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.

Marina Place

Gloucester
1 Bedroom
1 Bathroom

Walk to Good Harbor Beach from this charming one bedroom duplex apartment. Perfect for a couple's getaway, solo travelers, or small families.

Plaisance

Gloucester
3 Bedrooms
3 Bathrooms

A comfortable modern home nestled in a quiet, leafy neighborhood not far from Good Harbor Beach and the Bass Rocks Golf Club. From the pool and ping pong table to the oversize soaking tub, this house has something for everyone.

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 stroll in either direction will take you to the surf and sands of Good Harbor Beach or Long Beach.

Over By Good Harbor

Gloucester
4 Bedrooms
3.5 Bathrooms

The proximity to Good Harbor Beach makes this home perfect for your next beach vacation. Abundant beach views and multiple oversized decks invite you to sit back, relax, and experience the beautiful Atlantic Ocean.

Ships Bell House

Gloucester
3 Bedrooms
2 Bathrooms

Have it all at Ships Bell House, including amazing ocean and sunset views. Head over to sandy Plum Cove Beach or into the quaint village of Lanesville.

Two Beaches Cottage

Gloucester
3 Bedrooms
1.5 Bathrooms

Ideally situated between two of Cape Ann's best beaches, this renovated and updated home offers single-level living, a large yard with deck, and an outdoor shower.

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.

Perrywinkle

Gloucester
4 Bedrooms
2 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.

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