Family-friendly holiday 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.

Two bedroom Apt with a deck

2nd floor apt, located on Pleasant St, the main road into Historic downtown Marblehead. Cute deck, main entrance to apt is off the deck. The apt is only minutes walk from great restaurants, gym, yoga studio, bike /running trail. 15 min walk to the beach (4 min drive) and historic downtown and uptown where you will find tons of really great shops. The apt is tastefully decorated and is quiet.see house rules Dogs are very welcome, but need to be house trained + friendly with other dogs/people.

Harbor Hideaway

A uniquely detailed single-floor unit in a 2 unit house featuring a large kitchen/dining room, living room, and a private cozy veranda. Queen Bedroom & additional sleeping for 2 with a deluxe air mattress. This space is perfect for couples, families with young children, or a single person. Only one dog allowed no cats. This unit is on the lower floor of a two-family house occasionally you can hear steps from the upstairs. PLEASE note parking on site is very tight small cars compact SUVs only.

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.

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!

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!

1742 Marblehead Studio|Minutes to Salem|Parking

Inquire about our winter rental rates! KEY FEATURES: ☀️Reserved parking for 1 vehicle ☀️Fully equipped + stocked kitchen ☀️New stainless steel appliances ☀️Light and bright space with four oversized windows ☀️Smart 4K TV ☀️Keurig with complimentary coffee ☀️Family Friendly! We provide pack and play, high chair, bouncer and stroller. No need to overpack with all of that baby gear! ☀️Futon that turns into a full sized bed ☀️Lots of natural lighting

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.

Walk To Everything

NOTE FOR WORLD CUP 2026 TRAVELERS: Please be advised this property is not near Foxborough, MA. Roughly 1 1/2-2hrs by car. Much longer by public transportation. Steps from the harbor and minutes to the beach, this modern two-bedroom home has been completely renovated. Free parking on site and surrounded by shopping, food, and more--walking distance to everything you need.

Devereux Beach Suite steps from beach

Enjoy beautiful views from second floor detached guest house with king bed and private entrance. Spend a day at Devereux Beach or stand up paddle board through the harbor, it's only steps away! We are a short walk to downtown shops, restaurants and bars. We have beach chairs, two bikes and a cooler for our guests.