Holiday houses in Rocky Neck

Harbor House with Ocean Views

Welcome to our charming Airbnb in Gloucester, MA! Steps from Stacy Boulevard, our home offers breathtaking views of Gloucester Harbor. Easy stroll to nearby downtown restaurants, shops, and Pavilion Beach, just a 5-minute walk away. We provide private parking for two cars. Stage Fort Park w/beach/play area is walkable for kids, and Good Harbor beach and Wingaersheek beach are a short drive away. Whether relaxing by the water or exploring the local scene, our Harbor House is the perfect retreat.

Family · Location · Layout

Blue Magnolia

High in the treetops, this spacious apartment is only two blocks from the Atlantic Ocean! You'll enjoy 1400+ square feet with beautiful hardwood floors, an all-new kitchen, and your choice of two comfortable bedrooms -- one king and one queen. With a sleeper sofa, the apartment can sleep six total. This is a 2-flight walkup with private entrance, plus access to a large patio and well-established plantings including roses & a grassy yard. Offstreet parking in back if needed, thru driveway gates.

Location · Family · Beach

Harbor Lights: Seaside Cottage in East Gloucester

Forget your worries at Harbor Lights. Listen to the waves crash on Niles Beach from a rocking chair on the enormous screened-in porch. Enjoy quality time with your family after a great day at the beach. Take in the views of Boston’s skyline from the rocks overlooking the ocean (or from the new outdoor shower!) Soak up the sun while reading a great book. Harbor Lights has been a source of tranquility for generations, and now it’s your turn to find out what makes this charming cottage so special!

Location · Value · Kitchen

Luxury Portside Townhome Steps to Niles Beach

Escape to Niles Beach and experience the ultimate coastal getaway in our inviting 3 bedroom 3 1/2 bath townhome, just a short walk away from the serene Niles Beach in Gloucester. Perfectly situated for families, couples or friends looking to unwind by the sea. Explore Gloucester's historic harbor and waterfront, discover local seafood dining options and charming shops in downtown or take a scenic walk along Cape Ann's beautiful coastline. Book NOW and Experience the Magic of Gloucester!

Family · Location · Hospitality

Wonderful Rocky Neck home on Gloucester harbor

2 Bedroom with Loft, 1 Bathroom fully furnished Home on Gloucester harbor. Dead end street with 3 off street parking spots. Restaurants, local art gallery's, the beach all just a short walk away. Wake up with the sweet smell of ocean air and the sound of seagulls calling. Enjoy your breakfast with a million dollar view on the 4 season porch with 8 sliding windows overlooking the harbor. You could spend hours watching the boats go by as you read a good book with your fur baby on your lap.

Value · Location · Hospitality

Sunset Serenity-Entire Cozy Home-30 min to Salem

Imagine yourself waking up to the waves, enjoying a cup of coffee and watching boats travel between the Annisquam River and Gloucester Harbor. It’s an invitation to an unparalleled waterfront experience. Sunset Serenity offers 1,000 Sq Ft 2 beds 2 baths with one vehicle driveway. Our 1st floor features a spacious kitchen, open concept dining and living area. Upstairs offers 2 bedrooms with water view and full bath with clawfoot tub. Just minutes to downtown and 30 minutes to Salem.

Location · Comfort · Sleep quality

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

Family · Value · Shared spaces

Oceanfront Dock Escape ~ Kayaks & Paddleboards

This 4-bedroom house is in a prime location & has EVERYTHING you need for an amazing vacation to Gloucester, MA! • 13-minute drive to Wingaersheek Beach • 10-minute drive to Downtown Main Street in Gloucester • 2 inflatable Paddleboards • 4 Kayaks Available! • Outdoor Patio w/ Oceanfront Views • Large Jenga set • Fully Stocked Kitchen • Multiple Outdoor Spaces: Balcony/Deck • Family Friendly- Pack n Play & High Chair • Beach Essentials: Chairs, Umbrellas, Life Vests, Towels

Location · Family · Access

Ocean View | Walk to Downtown & Beach | Skylight

Welcome to C by the Sea! Our stunning Penthouse apartment is located in the heart of Gloucester, MA. This beautifully renovated 1 bedroom, 1 bathroom 3rd floor unit boasts breathtaking views of the Gloucester Harbor and Ten Pound Island and features stunning skylight windows, which flood the space with natural light. C by the Sea is located in a charming historic building, built in 1865, sleeps up to 4 people, and is just steps away from all that Gloucester has to offer!

Family · Location · Check-in

Luxury Townhouse in Downtown with Free Parking #2

Welcome to Gloucester, the beautiful fisherman city. This spacious home has a beautiful living space and an ocean view from the balcony. The home boasts numerous features including in-unit laundry and 2 free off street parking spaces. Enjoy the convenience of being close to the beach, downtown, and the prestigious Beauport Hotel. Indulge in the vibrant culinary scene with many restaurants just steps away. Don't miss this opportunity to stay in this coastal paradise.

Family · Value · Walkability

Stay at Smith Cove

Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features: ✓ Rocky Neck waterfront retreat perched above scenic Smith Cove ✓ Spacious deck with outdoor dining, grill, and front-row harbor views ✓ Open-concept living with 17-ft ceilings and floor-to-ceiling windows ✓ Loft-style sleeping space plus primary suite with sweeping water views See more photos, video tours, and local recommendations on IG @staycapeann.

Location · Condition · Nearby

Luxurious beach house w/ harbor views & near beach

There isn't a better location on Cape Ann! Rocky Neck is the oldest art colony in the US. This luxurious 1br boasts ocean views & was updated w/ designer & custom features. Not only can you walk to the beach, there are amazing restaurants across the street and a wine & cheese bar featuring local art you can peruse while having a cocktail. Come and enjoy sunsets from the deck and everything else Gloucester has to offer!

Location · Family · Nearby