Vacation rentals in Children's Island

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.

The Hideaway | Beach | Theater | Fireplace

The Hideaway is a modern luxury suite located right in the center of it all. You can stroll a 1/2 mile to the beach, cozy up to the fireplace, walk downtown, catch a show at the theater, or discover Boston, Salem (2 miles away), or other quaint seaside towns. Tucked around the corner from downtown Beverly, in a quiet and historic neighborhood. This suite is located in the lower level of our home, and you’ll have your own private entrance, queen bed, fireplace, desk, fridge, and full bathroom.

Hideaway House: Modern home, historic seaside town

Welcome to historic, coastal Marblehead! The Hideaway House is a fully renovated home in the center of downtown, steps from restaurants, shopping, museums, and breathtaking views of Marblehead Harbor & the Atlantic Ocean. With a two car garage & parking for 6, this home is convenient and private - just 3 miles to Salem and only 16 miles north of Boston. Enjoy central AC on hot days and a gas fireplace, high speed WiFi & 55” smart tv on chilly nights. Follow us on Instagram @hideawayhousemhd

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.

Winter Island Retreat

Effective 4/1/23, NON Owner occupied listings have a 3% impact fee that is charged on the total expenses associated with the rental. Winter Island Retreat is a OWNER OCCUPIED listing that is the place; For total relaxation. Watch the sunrise and experience the Atlantic Ocean. Enjoy your favorite beverage while rocking in an Adirondack chair on the patio. Inhale the smell of the ocean breeze and fragrant sea roses. Winter Island Retreat is an experience like no other in the Witch City.

Seadrift Inn - 2 bedroom 2nd floor apt by the sea!

We are at Salem Willows - family-friendly activities, the ferry, trolley, train, downtown, and nightlife are all close by. Seadrift is perfect for couples traveling together as it has two bedrooms, both with King beds, a large living room, and bathroom. You have a private entrance and it is located on the second floor. You can walk to four beaches within minutes, one is right outside your door. Salem has many historic landmarks and wonderful restaurants very close by. Come visit!!

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.

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.

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.

Old Town Marblehead Harbor Retreat Private Parking

Relax in this private 2-bedroom apartment in the heart of historic Old Town Marblehead. Enjoy 2 queen bedrooms, separate living room, private bath, kitchenette, private entrance, dedicated parking, washer/dryer laundry room and kayak access. Walk to Marblehead Harbor, Fort Sewall, beaches, waterfront dining, shops, and local favorites. Perfect for couples, small families, business travelers, Salem visitors, or FIFA fans seeking a charming coastal retreat.

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