Vacation rentals with a patio in Gloucester

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.

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!

Cozy Apartment at Green Landing (No Cleaning Fee)

We want your departure to feel easy and hassle free without a cleaning fee! Enjoy 2 floors of living space overlooking the changing tides and natural wildlife of the Green Landing Salt Marsh. This stylish and cozy one bedroom apartment is located on a scenic edge of Central Gloucester, just a short drive to Gloucester’s iconic beaches. Being within easy walking distance to the train station means guests can access Gloucester, as well Rockport, Salem and Boston, with or without a car.

The Mariner|Family Friendly|Backyard|Walk 2 Beach

KEY FEATURES: ☀ Sleeps 8 | 3 bedrooms: 1 King, 1 Queen, 2 Twins ☀ Cozy queen pull-out sofa for extra guests ☀ 2.5 freshly renovated spa-style bathrooms ☀ Bright, fully equipped kitchen + seating for 6 ☀ Fully fenced backyard oasis with patio, new grill & lounge seating ☀ Central AC for breezy summer days ☀ Fast WiFi + Roku Smart TV for movie nights ☀ Screened-in porch for morning coffee ☀ Beach kit included: umbrella, chairs, cooler & cart ☀ Serene primary suite with King bed 🏖️

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.

City Loft | Group Getaway | King Downtown Location

AMAZING downtown location boasting a modern feel + open-plan living, high ceilings, exposed brick + beams, cozy with ample room for 6 overnight guests. Downtown views from a natural light-filled living room + rooftop deck. Logan airport 45 min, 1/2 mile to train, 5 miles to Plum Island Beach + steps away from fabulous food + nightlife. Ideal base! Come stay for a night or a week at the best of what NBPT has to offer.

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!

Steps from Harbor, Pool, Backyard Garden, Parking

HIGHLIGHTS: • Marblehead Harbor - 4 houses away • The Barnacle Restaurant - 4 houses away • Private backyard pool • 0.2 Miles to Fort Sewall • 0.3 Miles to Gas House beach • 0.4 Miles to Old Town Marblehead • 300 Feet to The Barnacle Restaurant • Walkable to restaurants and shopping • Beautiful private garden • 1 King, 2 Twin and 1 Sofa Bed • 2-car off-street tandem parking spaces