Holiday 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

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.

Old Shoe Inn

This unique building was constructed in the late 1800's as a shoemaker's cabin and we had it remodeled in 2019 as a contemporary guest cottage. It overlooks our beautiful garden, and is at the base of the Old Burial Hill where Revolutionary heroes are buried. Less than a five minute walk to Gas House Beach, you can watch the sunrise, go for a swim and during low tide walk to Gerry Island. It's a 10 minute walk to shops and restaurants. The historic area around our cottage abounds with charm.

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.

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.

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!

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

Historic flat - Old Town - 5 min to Salem / Beach

This charming studio condo was part of the primary residence of the man, Ben Andrews, who mastered the first navy ship, the Hannah. There are now 6 condos in this brick home located in the heart of Old Town, Marblehead. Top floor (3rd). Newly remodeled and redecorated with modern furnishings. Downtown, walk everywhere! One queen bed, two queen tatami floor mattresses with sheets up in the loft, spare queen air mattress with sheets.

Salty Header Hideaway - Centrally Located

Welcome to The Salty Header Hideaway! A cheeky, coastal-chic crash pad in the heart of Marblehead—perfect for families, lobster lovers, and wandering witches alike. Nestled in the heart of Marblehead, this chic, family-friendly retreat offers stylish comfort, upscale touches, and walkable access to shops, restaurants, village dock, and old town alike. Kick back in style with comfy digs, kid-friendly perks, and salty vibes for days.