Winter Only: Chester Square
Gloucester
3 Bedrooms
3 Bathrooms
One level living with spectacular views in historic Annisquam Village.
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North Shore Long Term Rentals
Winter Only: Captain Dolliver Condo
Gloucester
2 Bedrooms
2.5 Bathrooms
Beautifully furnished 2-bedroom year-round rental in the 1764 circa home of Captain Dolliver located in the heart of Gloucester's Historic District.
WINTER RENTAL: Rose Cottage on Eastern Point
Gloucester
2 Bedrooms
2.5 Bathrooms
WINTER RENTAL - 2 bedroom and 2.5 baths available 10/1-5/31. Enjoy the water views from this delightful home that is set amongst the grand homes of the elegant, historic, scenic and private peninsula of Eastern Point and steps from a private beach.
Winter Rental: Glitter Bay
Gloucester
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: Todd Cottage
Rockport
2 Bedrooms
1.5 Bathrooms
This adorable 2 bedroom/1.5 bath cottage started its existence as a granite outbuilding of the main house, and is now part of a 3 building freestanding condominium group located on a quiet lane in the Pigeon Cove area of Rockport.
Winter Rental: Niles Beach Condo
Gloucester
2 Bedrooms
1 Bathroom
Close to Niles Beach this 2 bedroom/1 bath condo offers beautiful views.
Year Round: Magnolia Pied a Terre
Gloucester
2 Bedrooms
1.5 Bathrooms
Magnolia! This sparkling modern 2-bedroom 1.5 bath townhouse boasts breathtaking views of Magnolia Harbor and Gray Beach (both just a 2 minute walk away). Meander downtown to the quaint village of Magnolia.
WINTER RENTAL: Harbor's Corner
Gloucester
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
WINTER RENTAL: The Garden House
Rockport
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: West Wind
Gloucester
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: Parker House
Gloucester
4 Bedrooms
2 Bathrooms
Winter rental only. This renovated 4 bedroom Gloucester home is located within a stone's throw of the shores of the Mill River.
Winter Only: Cambourne Way
Rockport
3 Bedrooms
2.5 Bathrooms
This 4-bedroom home in Rockport's fabled South End is just down the street from Pebble and Cape Hedge beaches. The spacious second floor features large windows, high ceilings, an open flow living room, kitchen, dining room, and the master bedroom suite.