Family-friendly vacation rentals in Marblehead

Seaside Cottage

Here you are down the street from some of Marblehead's hidden gems such as Redds Pond, Browns Island & Old Burial Hill Cemetery. One car parking. 5 minute walk to the beach, shops & restaurants. Fully fenced in yard with turf grass. One bedroom with a low profile queen sized bed. In unit washer/dryer. Full bath with tub. Newly renovated kitchen with major appliances: stove, oven, dishwasher, fridge, Nespresso maker & microwave. Sheets & bath linens provided. Minisplit A/C. Home is all one level.

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.

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.

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!

Mid Town Marblehead 1 B/R Pvt. Wing w/Own Entrance

Charming bright 1 bedroom (queen bed) with spacious living area and large bathroom (handicapped accessible). Total privacy means you never have to see us unless you need assistance. Hardwood floors throughout and beautifully decorated. Kitchenette with full refrigerator and eating area. Comfortably sleeps 2 and has a roll away cot available for 1 more person. Conveniently located in the middle of town. Easy access to Salem and surrounding area. Parking for 1 car available.

Ocean Park Retreat

Bright and cheery 1 bedroom ground floor apartment with two+ car parking on quiet street in Marblehead's Ocean Park neighborhood, just steps from the ocean. Full size bed and pull-out full-size sofa in living room, private bathroom with in-floor heating, kitchenette with microwave, dishwasher, sink, double induction cook-top, refrigerator, and toaster oven. Laundry access. Walk to the waterfront, watch the sailboats drift by. Fifteen- minute walk to Historic town center.

Heart of Old Town Duplex (LEFT), Steps from Harbor

A well-appointed 2 story townhouse located in the heart of Old Town Marblehead and footsteps from Crocker Park overlooking Marblehead Harbor. Walking distance to everything! Our space includes 1 queen bedroom and 1 bathroom upstairs with a kitchen, dining room, and living room (with full sofa bed) downstairs. A private entrance right off main street allows for some R&R while being close to all that Marblehead has to offer. We look forward to hosting you!

The Salem House | First floor 2 bedroom apartment

Historic 1850 built colonial house with restored exterior and interior odes to Doric order architecture. Originally built for a leather factory owner named Thomas Looby, The Salem house is now a beautiful opportunity to visit Salem in a distinguished space. Exactly one mile from downtown with off street parking, staying here allows being away from the craziness of the city center while intimately experiencing Salem by staying in a historic colonial home.

Harbor View Suite

Harbor View Suite is a beautifully decorated two story Unit within a newly renovated Victorian house on the harbor located in Historic Old Town Marblehead, Massachusetts. This accommodation offers a rooftop terrace with panoramic views of the Harbor. Views of the harbor also from the kitchen deck. Perfect for families & friends.​ One dog allowed no cats please PLEASE note - parking on site is very tight small cars compact SUVs only

Iconic Historic Downtown Home with Patio & Parking

Experience the charms of a 1700s home while enjoying modern amenities, 3 bedrooms with en suite baths, dedicated workspace, private patio & entrance, and parking -- all in the heart of downtown! Just steps to the harbor, Crocker Park, restaurants, grocery store, and the best of Old Town, the location of this gem cannot get any better! This unit, part of a two-family home, features 4 original fireplaces and pine wood floors.

Antique Home - Steps from Harbor - Private Pool

Just steps from Marblehead Harbor, this antique home offers a private backyard pool and beautiful garden. Walk to The Barnacle (300 ft), Fort Sewall, Gas House Beach, and Old Town Marblehead — easy and walkable access to all. Features one king bed, two twins, and a queen sofa bed. Enjoy walkable dining and shopping plus two tandem off-street parking spots—your perfect coastal getaway with plenty of amenities nearby.