Holiday rentals in Children's Island

Samuel Tucker House - Downtown Luxury 2 Bed Condo

Presenting the newly restored Samuel Tucker House. Located in the heart of Marblehead's downtown and walking distance to local shops, restaurants and beaches, this bright and charming newly renovated 2 bedroom and 2 bath condo is a masterful blend of historic detail and modern design. Amenities include a private entrance, open concept living and dining areas that connect to a nicely appointed kitchen, fireplace, workspace, washer/dryer, central A/C, exterior dining area, and dedicated parking.

Peaceful, 1888 Mediterranean Manor by the Beach

Architectural charm in this newly renovated, eco-friendly guest suite, could be a destination in itself with a granite kitchen, open living/dining, large yard, patio, private outdoor fireplace and fountain, and brick courtyard. A block away are beaches, lighthouse, playgrounds and a seaside park. Beverly has historic theatres, top-notch dining, cafes and microbrews. Boston is conveniently 30 mins away; other attractions like museums, castles, trails, water sports and whale watching are nearby.

Heart of Old Town One-Bed (Right-side Duplex)

Enjoy this charming 2-story townhouse with private entrance built in 1900 with the quaint characteristics of an antique harbor side home. Located in the heart of Old Town, close to Crocker Park and overlooking the Harbor, it is walking distance to everything! Our space features a full kitchen, dining room and living room (with twin sofa bed) on the first level and 1 king bedroom with full bathroom upstairs. Also on the 2nd level is a study with day-bed and desk. We look forward to hosting you!

Redtop Retreat in Old Town

Discover this charming condo in the heart of Old Town Marblehead. Gleaming hardwood floors lead to a spacious living room with a decorative fireplace and views of Jeremiah Lee Mansion. The modern kitchen boasts granite counters and modern appliances. Enjoy the large dining room. With two bedrooms, two baths, and a loft, this home offers ample space and off-street parking. Enjoy Abbott Hall, the Public Dock, Crocker Park, shops, and restaurants steps away. Drive 10 minutes to downtown Salem.

Marblehead Tiny House

This new 360 square foot tiny house sleeps four comfortably. A mile from old town, down town, and just steps from Salem Harbor for breathtaking sunsets. The house is located in private, wooded back yard of our home. Kitchen is outfitted with small refrigerator, instant pot, air fryer, hot plate with pots and pans, microwave oven, blender, toaster, coffee maker, and electric tea kettle, as well as glasses, plates, flatware, etc for eating in. Kitchen table and chairs comfortably seats four.

Winter Island Retreat

Effective 4/1/23, NON Owner occupied listings have a 3% impact fee that is charged on the total expenses associated with the rental. Winter Island Retreat is a OWNER OCCUPIED listing that is the place; For total relaxation. Watch the sunrise and experience the Atlantic Ocean. Enjoy your favorite beverage while rocking in an Adirondack chair on the patio. Inhale the smell of the ocean breeze and fragrant sea roses. Winter Island Retreat is an experience like no other in the Witch City.

Seaside Studio Shipyard District

This lovely studio is less than 100 yards from the harbor and a 10-minute walk to downtown Marblehead. Located in a quiet neighborhood in the historic Shipyard District, the studio is a "semi-attached" addition to a New England-style home. The studio has a private entrance and a sliding door that opens to a patio by the garden. Guests are welcome to park their cars in our driveway. With about 400 square feet of floor space, it has a cathedral ceiling and top-of-the-line appliances.

The Knotical (private suite, separate entrance)

Downtown Marblehead! Separate entrance to a private one bedroom/one bathroom apartment with living area and efficiency kitchen. Enjoy your own space in the Shipyard District just of off Atlantic Ave, close to Old Town, yacht clubs, and Devereaux Beach. This is a separate space within a larger house with parking. The ceilings are low (this is Marblehead, after all), and the space is the downstairs unit of a three level house. Anyone over about 6 feet will need to watch their head!

House with Pool, 4 Houses from Harbor, Fort Sewall

Marblehead Harbor is just 4 houses away from this beautiful antique home with a backyard pool in Old Town Marblehead. This quaint cottage is surrounded by a beautiful garden and is just steps away from The Barnacle Restaurant. Walkable to attractions like Fort Sewall, Fort Beach, Gas House Beach and local shops and restaurants. Car-free convenience in Old Town Marblehead. Perfect for couples or families seeking a charming and convenient getaway that offers off-street parking.