Family-friendly holiday rentals in Swampscott

Two bedroom Apt with a deck

2nd floor apt, located on Pleasant St, the main road into Historic downtown Marblehead. Cute deck, main entrance to apt is off the deck. The apt is only minutes walk from great restaurants, gym, yoga studio, bike /running trail. 15 min walk to the beach (4 min drive) and historic downtown and uptown where you will find tons of really great shops. The apt is tastefully decorated and is quiet.see house rules Dogs are very welcome, but need to be house trained + friendly with other dogs/people.

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!

Modern & Cozy Apt close to Boston and Salem

New & Modern, Close to the beach , 15 minutes to the airport & BOSTON. Close to the beach, Salem, & Boston. 3 minutes away from the commuter rail 5 People can comfortably stay here. 3 minutes away from the commuter rail 10 minutes away from Salem 15 minutes to the Airport Several basic amenities included like snacks, water, mouthwash, toothbrushes, toothpastes, etc. Washing and Drying machine are included in the stay. Free Parking (Private Driveway) Smart TV with Netflix access included

Ocean Views at Casa de Mar near Salem & Boston

Relax and unwind at Casa de Mar - our 3 bed, 3 full bath ocean front home on the North Shore. Close to Salem and Boston, overlooking Swampscott Bay to Nahant. The great room has 25' ceilings, a 70" flat screen TV, and 2 seating areas. Modern kitchen, new appliances. The master bedroom has a king-sized bed, sitting area, flat screen TV, private balcony, and en suite bath. The first floor bedroom has a queen bed and a private balcony. The third bedroom has a queen bed and en suite bath.

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

Comfy & Cozy Apartment with Free Parking

Located in the historic and quiet town of Marblehead, this cozy apartment can home up to six people. There is one parking spot on the premises, but also plenty of street parking. Even though the apartment is located on one of the main streets in the heart of MHD, it is very peaceful. This location is close to everything you’d need and is very close to the historic district. We are pet friendly and you’ll find many games, toys and entertainment for you and your fur babies!

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.

Modern Victorian close to Salem

Welcome to The Ulman! Enjoy a stylish experience in our centrally-located historic condo. We are walkable to exquisite beaches and parks as well as downtown Swampscott where you will find shops, restaurants & bars to explore. If you feel like hanging in, share a meal in our well stocked kitchen or a cocktail in the parlor. Perfect for a couples getaway, small family or a group of friends looking to explore the North Shore.

Antique Home - Steps from Harbor - Private Pool

Just steps from Marblehead Harbor, this antique home offers a private backyard pool and beautiful garden. Walk to The Barnacle (300 ft), Fort Sewall, Gas House Beach, and Old Town Marblehead — easy and walkable access to all. Features one king bed, two twins, and a queen sofa bed. Enjoy walkable dining and shopping plus two tandem off-street parking spots—your perfect coastal getaway with plenty of amenities nearby.

Walk To Everything

NOTE FOR WORLD CUP 2026 TRAVELERS: Please be advised this property is not near Foxborough, MA. Roughly 1 1/2-2hrs by car. Much longer by public transportation. Steps from the harbor and minutes to the beach, this modern two-bedroom home has been completely renovated. Free parking on site and surrounded by shopping, food, and more--walking distance to everything you need.

Gorgeous Oceanfront Penthouse

A penthouse tastefully designed with breathtaking views of the ocean. Framed by spectacular sunrises with ever changing tides, this loft has a quartzite kitchen, and a luxurious bathroom w/a spring jetted tub. Your own private deck. A truly magical place. Ideal for Traveling nurses, work related assignments, short term furnished rental on the Northshore. Please inquire.

Devereux Beach Suite steps from beach

Enjoy beautiful views from second floor detached guest house with king bed and private entrance. Spend a day at Devereux Beach or stand up paddle board through the harbor, it's only steps away! We are a short walk to downtown shops, restaurants and bars. We have beach chairs, two bikes and a cooler for our guests.