Holiday rentals with a patio in Gloucester

KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN

🏖️Looking for the perfect Gloucester retreat for your group or family?🌴 Look no further than this spacious and inviting 2-bedroom unit🛏️, ideal for families and groups seeking comfort, style, and ample room to relax🛋️✨. Step inside and be greeted by a bright and airy living area🛋️, perfect for gathering together after a day of exploring all that Gloucester has to offer 🚤🏞️. With comfortable furnishings 🪑 and modern amenities📺🍽️, this unit provides the ultimate vacation experience🌴🍹.

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.

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.

Shore Cottage • Peaceful Coastal Retreat

Tucked away in a quiet, private residential neighborhood, our cozy cottage offers the ideal home base for your Gloucester getaway. Located just steps from the city’s famous boulevard, beautiful beaches, and a variety of local hotspots, you’ll have the best of Cape Ann at your fingertips. The cottage sits behind the main house on the property, offering a peaceful retreat with all the comforts of home. Whether you’re out exploring or simply kicking back and relaxing, this is your place to unwind.

Seacoast Getaway

Seacoast, NH’s popularity is well-earned, with museums, the finest restaurants, spas and shopping that blend perfectly with the Seacoast landscape. From our beautiful beaches and coastline combined with plentiful outdoor recreation, including fishing and whale watching, kite flying and more with Portsmouth, Rye, Exeter and Kittery Maine, all a short ride our beachfront condo has something for all. After a day of outdoor activity and exploring, come retire and rest in our place with a view.

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, full kitchen, queen sized bed with en-suite bathroom and a sun room that converts to an extra sleeping space perfect for kids. A 5 minute 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.

Condo at the Cut

Welcome to The Condo at The Cut, an oceanfront Gloucester gem where almost every window frames the sea and the spacious covered deck captures both sunrise and sunset. The open layout connects living, dining, and a fully equipped kitchen, with WiFi and YouTube TV for convenience. Just minutes from Good Harbor Beach, Stage Fort Park, and downtown dining, shops, and bars. Perfect for families, couples, or friends seeking a true Cape Ann escape.

Shoreview Studio Lounge

This historic Victorian residence, is today host to this seaside studio lounge. Once inside, you’ll fall captive to the seascape off Independence Park. The Atlantic panorama provides an awe-inspired sunrise daily. From its elevated perch, the studio has a contemporary feel with its private observation deck to its sophisticated lighting and wet bar design. Comforts include heated floors, air conditioning and powered room-darkening blinds.

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.

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!