Family-friendly holiday rentals in Marblehead

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.

4 Bed Water View w/ Parking

Your family and friends will be close to everything when you stay at this centrally-located home. Steps to the Ocean and walk into historic Bearskin Neck. Enjoy panoramic coastal views from the family room, kitchen and master bedroom. Deck space to enjoy outdoor dining, glass of wine, or a morning cup of coffee. Everything to do in Rockport is a short walk from this downtown home. Restaurants and coffee shops, Art Galleries, shopping and the town beaches are steps away. Parking spots included.

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!

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.

Antique Garden Cottage

Ours is a cozy, 2 bedroom & living room suite in an antique garden cottage with private bath and entrance and on site parking. It is attached to our home but is a separate private space with no shared living areas and its own patio English Garden. It is situated on 2 floors (bathroom upstairs). It is a short walk to beaches, shops, restaurants & historic sites. The suite has a small breakfast table, microwave, minifrig, Keurig, electric kettle & toaster, but not a full kitchen.

Beautiful Kitchen | Deck | Yard | Salem/Marblehead

This charming and recently renovated 3-bedroom, 1.5-bathroom house is the perfect retreat for your New England family getaway. Nestled directly between historic Marblehead and Salem downtown, you'll find yourself surrounded by the rich maritime history and colonial charm that these picturesque towns have to offer. Enjoy charming downtown Marblehead or enjoy the bewitching ambiance in Salem. Come home to glass of wine on the deck while the kids play freely in the backyard.

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.

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

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.

Cozy Coastal King Suite | Steps to Beach & Town

Unplug in this private, standalone suite with ocean views in Marblehead. Walk steps to Devereux Beach or ride our complimentary bikes to Old Town’s best cafes, dining, and shops. Minutes from historic Salem! Features a luxury king bed, smart TV, dedicated workspace, full bath, cooler, and beach chairs. Enjoy total privacy, a reserved off-street parking spot, and 24/7 keyless check-in for the ultimate New England escape.

Pool Is Open in Sept! Steps from Harbor + Old Town

HIGHLIGHTS: • Marblehead Harbor - 4 houses away • The Barnacle Restaurant - 4 houses away • Private backyard pool • 0.2 Miles to Fort Sewall • 0.3 Miles to Gas House beach • 0.4 Miles to Old Town Marblehead • 300 Feet to The Barnacle Restaurant • Walkable to restaurants and shopping • Beautiful private garden • 1 King, 2 Twin and 1 Sofa Bed • 2-car off-street tandem parking spaces