Holiday rentals in Marblehead

Yachtsman Suite – Nautical Coastal Stay in Histori

Experience Marblehead’s seafaring charm at the Yachtsman Suite, a bright nautical retreat in the heart of historic Old Town. Just steps from the harbor, coastal walks, beaches, and waterfront dining, this first-floor suite offers the perfect blend of seaside character and modern comfort. Start your day with a harbor stroll, explore nearby landmarks and scenic shoreline paths, or enjoy fresh seafood at local favorites — all within easy walking distance. Perfect for couples, weekend getaways, 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.

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!

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.

Amazing Location! New2 Bed downtown w AC sleeps 4

Dockside - Stunning newly renovated First Floor apartment in the heart of Historic Old Town Marblehead. A stone’s throw from Maddies, The Landing, shopping, and right next to the Driftwood Diner for the best breakfast Steps to the harbour where you can easily access local yacht clubs and a public launch service is available for Harbour tours. Prime parking, AC,classic details and a fresh modern space and amenities will provide you with a very relaxing stay in our beautiful Seaside village

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.

Mugford Manor

This charming one-bedroom apartment is located on the second floor of the Samuel Striker House, built in 1725. Our property is within whistling distance to Old Town Marblehead, rich in colonial and revolutionary history and provides numerous shopping and dining options. Conveniently situated near the MBTA bus stop and only a ten-minute drive from downtown Salem, which features a variety of attractions and amenities. 1 queen bed, 1 queen pull-out couch Ample street parking available.

Modern, thoughtfully set-up in heart of town

Features 🌟Located in the heart of Marblehead, perfect for exploring local shops, dining, and historic sites 🌟Cozy modern home with a welcoming atmosphere and stylish interiors that blend warmth and comfort 🌟Mini split units with remote for AC and heat 🌟Beach essentials included (towels, chairs, and an umbrella) 🌟Parking available in front of the home and free street parking around the house 🌟Board games 🌟Air purifiers 🌟In unit washer and dryer 🌟Wine available for purchase

Captain’s Quarters

Tucked in a home built in 1740, this cozy apartment offers costal charm in historic old town, surrounded by antique homes and winding streets. Galleries, bakery, cafés, shops, restaurants, and beaches are a few steps away. Unwind, explore & soak in the salty, seaside breeze. Note: The apartment is on the 2nd floor. Typical of 18th century homes, the staircase is steep and narrow. The apartment isn’t child proof or de-leaded. Wear shoes because the original floor boards are rough.

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.

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.

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