Holiday rentals with a patio in Rockport

Deluxe oceanfront home sleeps 4 open concept

Three words: On the water. ❤️ Airy, sun-filled cottage offers ocean views 🌊 and deck overlooking harbor. Newly renovated with open-concept style, cathedral ceilings, and flexible sleeping 💤 for 4–6: king bed in loft, two queen sleep sofas and Murphy bed. Unique with free-flowing shared spaces; creatively curated design. Art gallery 🖼️ with original works displayed in house. Clean, stylish, uncluttered – perfect mix of comfort and coastal charm. A rare find: oceanfront + in town. This is it! ⭐

4 Bed Water View w/ Parking

Your family and friends will be close to everything when you stay at this centrally-located home. Steps to the Ocean and walk into historic Bearskin Neck. Enjoy panoramic coastal views from the family room, kitchen and master bedroom. Deck space to enjoy outdoor dining, glass of wine, or a morning cup of coffee. Everything to do in Rockport is a short walk from this downtown home. Restaurants and coffee shops, Art Galleries, shopping and the town beaches are steps away. Parking spots included.

The Admiral's Loft: Private Deck and Ocean Views

The Admiral's Loft sits high in the treetops with keyhole views of the bay from a private deck. It is close to town but set back on a quiet dead-end street. Beaches are walking distance from the house- we have beach supplies for you. Marble countertops, tiled shower, hardwood floors, leather couch and antique furniture make this a luxurious feeling space. A/C throughout. On the deck there is a long couch for two people to lay out on, umbrellas, a dining space for 4 and an electric grill.

Cozy Oceanfront Beach Cottage - Walk to Downtown

Escape from reality to this intimate, coastal cottage located across the street from picturesque Back Beach and just a short walk to the galleries, shopping, and restaurants of Bearskin Neck. Imagine waking up to breathtaking ocean views and enjoying your morning coffee on the patio before heading across the street to relax and unwind on the beach. This seaside haven blends charm with modern comfort, perfect for couples, small families, or solo travelers looking to relax and explore Cape Ann.

Gingerbread House | Hot Tub | Dog Friendly

Our historic carriage house in Downtown Rockport has everything you need for the perfect getaway, all year long! A two-minute walk to beaches, shops, galleries, parks, and playground. A peaceful family and pet-friendly space with all the amenities you need for a comfortable stay: laundry, kitchen, queen sized bed with en-suite bathroom and sun room that converts to an extra sleeping space perfect for kids. A short walk to the train for day trips to Salem, Gloucester, and Boston!

Pleasant Place

Pleasant Place is a spacious, clean and centrally located spot to spend time with your family and friends. It has two bedrooms, two full bathrooms and a pull out couch. Sun soaked in natural light, it boasts a newly renovated kitchen, granite island, large dining room and a charming family room with views of the Rockport harbor. Walk downtown, to the beach, or drive around town and take advantage of your own parking spot in the busy summer.

Ocean views! Welcome to Sea Breeze! Winter rates!

Sea Breeze offers a spacious, newly renovated, 4 bedroom escape, that smiles down upon Good Harbor beach. Take in the refreshing salt air breezes while enjoying the solitude of being situated at the end of a quiet cul de sac. A short 3-5 minute drive gets you into the Good Harbor parking lot or take a 20 minute walk instead. Close-by downtown Gloucester is teeming with spectacular restaurants and activities for the whole family.

Rare Waterfront Luxury Penthouse|Bearskin Neck

☀ Oceanview waterfront deck with outdoor seating ☀ 3rd-floor penthouse walk-up (stairs, no elevator) ☀ 1 bedroom + 2 full-size sleeper sofas ☀ Renovated modern bathroom with spacious tiled shower ☀ Modern kitchen with large island seating for 6 ☀ Central AC for hot summer days ☀ Hi-Speed WiFi, 2 Smart TVs & Sonos speaker ☀ Washer/dryer in unit ☀ Rare California King bed ☀ Steps from downtown Rockport & Shalin Liu Theater

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!

Downtown Cottage-DeckツParkingツOceanツBeachesツShopsツ

Discover coastal charm at this historic Rockport, MA gem! Breathtaking seaside views, beaches, cafes, art shops, and the Shalin Liu Performance Center nearby. Walk to iconic Motif #1, kayak, hike, or unwind at the beach. Explore nearby Salem, MA, known for its witch trials history, or take a day trip to bustling Boston, just a short drive or train ride away. Experience the best of New England coastal living. Book now!

Charming waterfront home. Patio, AC, Shops, Dining

Discover your dream Rockport getaway! You'll stay nestled on Bearskin Neck, in this cozy harborside condo boasting stunning views, steps from shops, beaches, & galleries. Relax on your private patio overlooking the iconic Motif #1 for your morning coffee or evening happy hour. Book now for a fun getaway, year-round! There is one bedroom upstairs and a pullout sofa downstairs that can sleep 2.

Walk To Downtown and Ocean, Large Private Yard

Private Two Bedroom with Backyard -1 mile walk to historic downtown Rockport; shops and restaurants -1 mile walk to Front Beach, very family friendly -Fast Wifi, 2 Queen Beds, kitchenette with coffee and tea -Quiet, private yard space with firepit - very cozy! -Family friendly space! -Off street parking for 2 cars -Walking distance to town EV chargers Follow us @highsthavenrockport