Vacation rentals in Marblehead

Sailor’s Retreat – Old Town Stay Near Salem & Harb

Stay in the heart of Marblehead’s historic Old Town at Sailor’s Retreat, a comfortable first-floor coastal escape just steps from the harbor, scenic shoreline walks, and local dining. With nearby beaches and Salem’s historic attractions only minutes away, this location makes exploring the North Shore easy. Spend your days strolling harbor paths, visiting Fort Sewall and Crocker Park, or discovering Salem’s renowned museums and historic sites. Return to a welcoming space designed for comfort and

Location · Check-in · Comfort

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.

Family · Value · Beach

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.

Location · Family · Heating

Old Town Gardens, Private Getaway

Sunny Apartment deep in Marblehead's Historic District. A hidden gem built in 1800, lovingly restored with original pine flooring but completely updated kitchen, bath, high speed Wifi, Roku TV, A/C and heating. Private entrance, off street parking and secluded patio lead to your 1250 SF first floor apartment: 2 bedrooms, small office w/full size laundry, spacious dining room, chef's kitchen (gas, dishwasher) bath (soaking tub/shower) and living room overlooking the stunning front garden.

Family · Location · Beach

Captain’s Quarters

Tucked in a home built in 1740, this cozy apartment offers costal charm in historic old town, surrounded by antique homes on winding streets. Galleries, bakery, cafés, shops, restaurants, harborside parks and beaches are steps away. Explore, unwind, and soak in the salty, seaside breeze. Note: The apartment is on the 2nd floor. Typical of colonial era homes, the stairs are steep. The apartment isn’t child proof. Wear shoes indoors because the original floor boards from 1700s are rough.

Family · Value · TV

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.

Location · Family · Wifi

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.

Family · Value · Walkability

Little Harbor House 1st Floor

This private two bedroom apt is on the 1st floor of our 1713 home. It is up 15 exterior steps to the deck, through the front door and to your private entrance. This is a beautiful, historic sailing community. It’s a 5 minute walk to restaurants, quaint shops, beautiful parks, and 1 minute to the waterfront. Sorry, but no smoking or vaping anywhere on the premises. Children visitors/guests must be 10 or older. Any visitors must be on the confirmed guest list. On street parking.

Value · Location · Layout

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.

Family · Location · Long stay

Jersey St Lovely

Beautiful Harbor views of Salem Harbor from a classic New England home for your vacation! A friendly neighborhood. In the summer the back deck for lunch. Dinner on front porch for sunset watching. Upgraded kitchen & bath make for comfortable living. Short walk to downtown. Up street from a beach!! Note-separate apartment is attached to house. However there is no shared common space! The house has the entire front porch & back deck.

Value · Family · Accuracy

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.

Value · Location · Heating

Salty Header Loft | Bright 2BR Retreat

Welcome to Salty Header Loft, a bright, thoughtfully designed 2-bedroom retreat in the heart of Marblehead. Walk just 10-15 minutes to downtown, the harbor, shops, restaurants, Crocker Park. Minutes from Salem, it's the perfect home base for Haunted Happenings without the crowds. Enjoy a private covered porch, off-street parking, Level 2 EV charging, fast Wi-Fi, a full kitchen, and in-unit laundry. Stay Salty!

Location · Family · Indoor spaces