
Family-friendly holiday rentals in North Shore
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Top-rated family-friendly rentals in North Shore
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Winter retreat & waterviews in downtown Rockport
Rockport is charming over the holidays with lights, music and shopping! This brand new waterfront apartment is in a historic home with onsite parking & a private entrance. Galleries, restaurants, coffee shops, live music and shopping on Bearskin Neck are steps away. Features full kitchen and bathroom with new applicances and fixtures. Living room has a loveseat, swivel chair, dining table, coffee table, roku TV, games, puzzles & books. Kitchen has a fridge, stove, oven, microwave and Keurig.

Annisquam Village Bunny Cottage
This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

Victorian Near Beaches, 2nd Floor of 2 Family Home
Great location for visiting Boston and the Northshore of MA. Close to Endicott & Gordon Colleges. Very safe residential neighborhood, only a short walk to 3 beaches, seaside park, quick market, steps to coffee shop. 4 miles from downtown Salem, MA, USA. Close to commuter rail inbound to Boston or out to Rockport/Gloucester. Sleeps 4, 2 bedrooms, 1 1/2 baths, fully equipped kitchen, dining rm, living rm, attic loft with platform bed, W/D, front porch for relaxing with private entrance & parking.

The Hideaway | Fireplace | Downtown | Theater
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.

Cozy place to relax! 14min to Salem - 25 to Boston
Due to your allergies, we are unable to Host any animals Private entrance-Basement - H 6' - entrance 5' 6" Relax in this calm, stylish space after a day of exploration! Perfect for travelers /work trips. Stay with US! I live on-site to ensure a safe and welcoming stay You will get to enjoy: - Salem MA - - Boston MA - Beaches - Beverly MA - Gloucester MA - Marblehead MA - Trails Our mattress is fairly firm, which can provide a very good night sleep! - Illegal activities will be reported -

Rocky Neck Studio/Loft, Gloucester, Mass.
Welcome 2026! We look forward to you visiting RockyNeck in Gloucester. You will be sure to enjoy various special activities and events this summer and fall. We are located in the "quiet end", on a private residential dead end street in a historic artist colony . Nearby public transportation, Audubon sites, cultural events, the Gloucester Stage Co and beaches . Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV

Beverly Farms Apartment “Homeport”
"Homeport" - A nautical themed apartment, nestled in the small coastal village of Beverly Farms. The village has cafes, restaurants, beaches and is nearby “Witch City” Salem MA. Homeport has a private entrance, den, two bedrooms, 1.5 baths with essential amenities and guest parking. The local area is famous for beaches, museums, galleries, eateries and many historic attractions. Explore the North Shore or take a commuter train to explore Boston, saving time and expense of driving.

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.

The Solar Powered Dogtown Cabin at Applecart Farm
Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

Halibut Point State Park. Nature Lovers Retreat
"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.

Ipswich Apartment
This apartment has a private entrance in downtown Ipswich, close to restaurants and the commuter rail for Salem and Boston. From May to September, the nearby CATA shuttle makes it easy to reach Crane Beach and the town of Essex, known for its clams and antique shops. Ipswich also offers river cruises, kayaking, canoeing, and fishing. Enjoy the local attractions!

It’s better to wake at the Lake 2BR guest suite
Overlooking Chebacco Lake, your rooms are downstairs in a private level. There are 2 bedroom available for use downstairs along with a big living area a coffee/tea bar and a bathroom with shower on this level. You can access to the lake for swim, kayak, canoe or if you come in the winter you can icefish, ice skate, cross country ski or snowshoe too.
Popular amenities for North Shore family-friendly rentals
Family-friendly home rentals with a hot tub

Nana-tucket Inn

Hot Tub! Nothing beats it on a winter night!

Luxurious Oceanfront Property

Haven by the Lake

Luxurious Spa Suite: Sauna, Jacuzzi, Steam Shower

Oceanfront Pool. Close to Boston. Free Parking.

Winery Studio w/ Private Hot Tub+Fireplace+Tasting

Little Lake House, the Bungalow
Family- and pet-friendly home rentals

Two bedroom Apt with a deck

KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN

Enjoy Stunning Sunrises&Sunsets Ocean Views 33

Private Newburyport Studio w/bath

Harbor View Suite

Quirky room above convenience store, near water.

Hidden Gem! Short term rental steps from 2 beaches

Large, Comfortable & Conveniently located Home
Family-friendly home rentals with a pool

Hopkinton Mass 3+ Bedrooms - Great location!

The Haven at Doherty Homestead

Cozy Private Suite halfway between Cape & Boston

Luxury suite with room divider near downtown

Stylish and Cozy at Revere Beach

Country Cottage in the City

Cozy Private Studio Unit w/ Laundry and Parking!

Sunset Waterfront Privacy Beach
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Pet-friendly rentals North Shore
- Loft rentals North Shore
- House rentals North Shore
- Rentals with breakfast North Shore
- Waterfront rentals North Shore
- Rentals with a washing machine and dryer North Shore
- Rentals with outdoor seating North Shore
- Cottage rentals North Shore
- Smoking-friendly rentals North Shore
- Rentals with lake access North Shore
- Private suite rentals North Shore
- Hotel rooms North Shore
- Rentals with a fireplace North Shore
- Rentals with a hot tub North Shore
- Rentals with an EV charger North Shore
- Rentals with pools North Shore
- Townhouse rentals North Shore
- Rentals with a firepit North Shore
- Bed and breakfasts North Shore
- Rentals with beach access North Shore
- Boutique hotels North Shore
- Rentals with a patio North Shore
- Flat rentals North Shore
- Fitness-friendly rentals North Shore
- Rentals with a kayak North Shore
- Beachfront rentals North Shore
- Apartment rentals North Shore
- Guest house rentals North Shore
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Hampton Beach
- TD Garden
- Fenway Park
- Harvard University
- Boston Common
- Ogunquit Beach
- Wells Beach
- Revere Beach
- Freedom Trail
- New England Aquarium
- Long Sands Beach
- MIT Museum
- Boston University
- Boston Seaport
- Canobie Lake Park
- York Harbor Beach
- Crane Beach
- Boston Convention and Exhibition Center
- Duxbury Beach
- Museum of Fine Arts
- Quincy Market
- Gillette Stadium
- North Hampton Beach
- Prudential Center
- Things to do North Shore
- Sightseeing North Shore
- Food and drink North Shore
- Things to do Massachusetts
- Nature and outdoors Massachusetts
- Food and drink Massachusetts
- Sightseeing Massachusetts
- Art and culture Massachusetts
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