Gloucester, MA Houses for Rent

SHORT OR LONG TERM RENTAL Fall/Winter rental availability....Rare opportunity to rent this spectacular custom-built home in the Private section of Wingaersheek Beach. Stunning ocean views from every room of this 4-bedroom home. Large bedrooms, custom bathrooms, beautiful chef's kitchen leads to a 2-story family room w/ fireplace and direct access to an oversized deck with stunning ocean views.

Gianni De Palma GDP Real Estate Group, LLC

SPECIAL SEASONAL RENTAL! Available September 13, 2025 - June 13, 2026. Situated in the heart of ever-desirable Annisquam, this thoughtfully appointed 3 bedroom, 2.5 bathroom home provides modern comforts and exceptionally charming character. Highlights include a wood-burning fireplace in the cozy sunken living room, and an expansive eat-in kitchen with stainless steel appliances, a farmhouse

Paula Polo-Filias J. Barrett & Company

September & October dates available! Modern Cape Ann coastal retreat. Sitting on 1.4 waterfront acres with granite outcroppings, mature trees, and gardens. Private deep-water dock, 5 feet at low tide, accommodates 2-3 boats. Riverfront peninsula with sweeping water and marsh views, perfectly located in the middle of the Annisquam River. Take trips out to Ipswich Bay, the bustling Gloucester

John Farrell Coldwell Banker Realty - Beverly

*SEASONAL RENTA OCT 1 - MAY 31, 2026L* Charming three-bedroom home in quaint Annisquam Village available October 1 through May 31, 2026. Recently renovated with hardwood floors, stainless steel appliances, and marble countertops. Features a large three-season porch in the front and a private patio in the rear. Amenities include washer/dryer on the first floor, ample closet space, full basement,

Katelyn Ciaramitaro Engel & Volkers By the Sea

This serene waterfront vacation home offers breathtaking views from nearly every room. Enjoy the private dock for boating, swimming, and kayaking, surrounded by cedar trees for privacy and a nature-filled experience. Relax on the screened-in porch or stroll the sandbank at low tide. Located on picturesque Rust Island, just a short drive from Gloucester and Rockport, the property includes a fully

Julia Virden J. Barrett & Company

Welcome to this charming historic 3 bed 2 bath house, where old-world charm meets modern amenities. This beautifully restored home features original 'Kings Timber' floors throughout the living room, office, and formal dining room, each equipped with exposed beams and a cozy fireplace. Just past the first-floor full bath with a jacuzzi tub and laundry space is a fully updated kitchen with

Timothy Kotkowski The Proper Nest Real Estate

--SHORT TERM RENTAL -- Price is a base price and per week. Inquire for longer stays. Private oceanfront Wingaersheek Beach house features five bedrooms, three bathrooms and has recently been renovated with custom steel front double doors, new wood floors, pine interior paneled walls, new kitchen cabinets, counters, bathrooms, and mini split AC units. The house spans three levels along with an

Stephen Sassoon Sassoon Group, LLC

WEEKLY SUMMER RENTAL in spacious, well-appointed family home on privately situated, green leafy lot, yet less than half a mile away from the Good Harbor Beach Footbridge. With Bass Rocks Golf Club and tennis courts around the corner and Rocky Neck and downtown Gloucester a short distance away, this is a prime location for fun with friends and family. Generous kitchen opens to family room with

Amanda Armstrong Compass

OCEANFRONT IN LANESVILLE SUMMER RENTAL WITH DATES STILL AVAILABLE STARTING IN MID-AUGUST. Idyllic summer retreat in stunning and private oceanfront setting in one of the North Shore’s most scenic communities. This is the perfect base for exploring the many delights of Lanesville, from its rugged shoreline to colorful Lanesville village with its studios and cafes. Head to beautiful Lane’s Cove,

Amanda Armstrong Compass

Short term monthly rental opportunity from October 1st- May 31st! Owners will consider any length of time within those dates. Newly renovated cottage just 600 feet from Long Beach in Rockport. Conveniently located within a 5 minute drive to both downtown Gloucester and Rockport. This charming getaway features 4 bedrooms consisting of 1 king, 2 queens, and 2 twins, providing a blend of comfort and

Daniel Resop William Raveis R.E. & Home Services