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North Shore Long Term Rentals

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West Wind

4 Bedrooms
2 Bathrooms

Overlooking the Ipswich Bay in Annisquam, this tastefully renovated ranch is comfortable and pretty with some of the best views on Cape Ann! Available for winter rental.

Winter Rental: Rocky Neck Lookout

2 Bedrooms
1 Bathroom

This delightful two bedroom light-filled furnished apartment has great views of Smith's Cove. Located at the entrance to Rocky Neck, it is a short walk to art galleries, restaurants, community theater, and boutiques.

WINTER RENTAL: The Garden House

3 Bedrooms
2.5 Bathrooms

South end of Rockport with tranquility and privacy, but just a mile from town and commuter train and everything the quaint village has to offer. Comfortable home with 3 beds/2.5 baths family room, living room and wonderful mature grounds.

Winter Rental: Glitter Bay

3 Bedrooms
1.5 Bathrooms

This historic gem in Gloucester's coveted Annisquam district overlooks the glittering waters of the Annisquam River, Ipswich Bay and the Annisquam Yacht Club. Since the view faces south, you can enjoy both sunset and sunrise from the wraparound porch.

Winter Rental: Harbor's Corner

1 Bedroom
1.5 Bathrooms

Within sight of the famous footbridge leading to the white sands of Good Harbor Beach. This bright and sunny winter rental condo at the Thorwald Condominiums offers an ideal winter rental opportunity