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
Year Round: Hammond House
Gloucester
2 Bedrooms
1 Bathroom
Delightful year round 2 bedroom home in East Gloucester. The spacious first floor includes living room, den, dining room with pantry all with gleaming hardwood floors.
Winter Rental: Rocky Neck Lookout
Gloucester
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: 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 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.
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 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: Bay View House
Gloucester
3 Bedrooms
2 Bathrooms
Tucked away 3 bedroom home offers privacy and quiet. Beautiful views of Ipswich Bay in one directions. Woods and walks into Dogtown in the other direction.
Winter Rental: The View on Bearskin Neck
Rockport
1 Bedroom
1 Bathroom
From the deck of this New England vacation rental home are picturesque views of Rockport Harbor and iconic Motif #1, the area's prized historical landmark. Minutes from delightful shops and restaurants in Rockport.
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: High Rock Cottage Apartment
Gloucester
1 Bedroom
1 Bathroom
Good Harbor Beach and Long Beach are just a 5-minutes stroll from this sweet suite with its own deck, granite kitchen, separate living area with flat screen, full bath with tub and shower, a queen bedroom, and parking for one car.
Winter Rental: Rockport Seaside Retreat
Rockport
4 Bedrooms
2 Bathrooms
Charming vacation rental home situated just 300 yards from Whale Cove. Just one mile to a sandy beach or into the village of Rockport with its shops, restaurants, galleries and a world class Performance Center.
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.