Vacation rentals with a patio in Gloucester

4.99 out of 5 average rating, 132 reviews

The open kitchen features a large island with seating for several guests. A cozy living area is visible, with a comfortable seating arrangement and large windows allowing natural light and ocean views. Warm wood flooring complements the airy atmosphere.

Apartment in Rockport

4 Bed 2.5 Bath Water view Downtown with 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.

4.98 out of 5 average rating, 161 reviews

The entrance to the carriage house is framed by a welcoming black door, adorned with a seasonal wreath. Soft lighting from a lamp illuminates the pathway, while lush greenery and flowers create a serene atmosphere around the doorway.

Guesthouse in Beverly

Adorable 1-bedroom carriage house

Kick back and relax in this quaint refurbished carriage house, centrally located in Beverly, Massachusetts. The first floor offers a kitchen space (complete with a toaster oven and mini fridge) and a dining area, as well as a spacious living room set that is perfect for nights in after a day of exploring. If you prefer, the patio also has cozy outdoor seating! Upstairs, you can find a comfortable Queen-sized bed, a private bathroom, and a desk space that's perfect for working from home.

4.99 out of 5 average rating, 127 reviews

The historic carriage house is presented in a charming turquoise color, surrounded by lush greenery and flowering plants. Tall windows provide ample natural light. A spacious yard is visible, framed by a low stone wall and iron fence.

Guesthouse in Rockport

Gingerbread House | Steps to Beach| 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!

Superhost

A spacious private deck overlooks the tidal Annisquam River, featuring comfortable outdoor seating with blue cushions. A small table is placed beside the seating area. String lights illuminate the space, enhancing the inviting atmosphere for relaxation while enjoying scenic water views.

5 out of 5 average rating, 5 reviews

PVT Waterfront Deck|Firepit|Workspace|Free Parking

Welcome to your waterfront escape in Gloucester! Nestled along the a portion of the tidal Annisquam River, this professionally designed 3-bedroom home offers the perfect mix of relaxation and functionality for families and business travelers. Enjoy stunning tidal views, a private desk for remote work, and a fully loaded kitchen. Unwind by the electric fireplace, gather on the large private deck with a gas firepit, or explore nearby shops, restaurants, and beaches. Free parking included!

4.96 out of 5 average rating, 48 reviews

This bedroom features a queen bed with a soft cover and quality bedding. A wall-mounted mirror and a desk are positioned near the window. Natural light illuminates the space, highlighting the peaceful views of the Green Landing Salt Marsh.

Apartment in Gloucester

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.

A modern kitchen is highlighted by a large central island with seating for four. White cabinetry contrasts with a tiled backsplash in soft green tones. A sleek range hood is positioned above a gas cooktop, while steps lead to the upper level to the right.

4.98 out of 5 average rating, 41 reviews

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. Enjoy a 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 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.

Cottage in Lakeside Marblehead

The inviting backyard features a clear pool reflecting a serene atmosphere. A patio with seating is visible near the pool. The house, with large windows, provides a bright indoor space that overlooks the outdoor area, surrounded by lush greenery and charming landscaping.

4.98 out of 5 average rating, 129 reviews

House with Pool, 4 Houses from Harbor, Fort Sewall

Marblehead Harbor is just 4 houses away from this beautiful antique home with a backyard pool in Old Town Marblehead. This quaint cottage is surrounded by a beautiful garden and is just steps away from The Barnacle Restaurant. Walkable to attractions like Fort Sewall, Fort Beach, Gas House Beach and local shops and restaurants. Car-free convenience in Old Town Marblehead. Perfect for couples or families seeking a charming and convenient getaway that offers off-street parking.

The exterior of a charming home is showcased, featuring a spacious backyard with a neatly manicured lawn. A patio area includes cushioned seating arrangements, and a grill is positioned nearby. The structure has multiple windows, surrounded by greenery and a clear blue sky.

5 out of 5 average rating, 43 reviews

The Mariner|Family Friendly|Backyard|Walk 2 Beach

KEY FEATURES: ☀ Sleeps 8; 3 bedrooms, 1 king, 1 queen,+ 2 twin ☀ Comfortable queen sized pull out sofa ☀ 2.5 Newly Renovated Bathrooms ☀ Modern and well-equipped kitchen with seating for 6 guests ☀ Fully fenced in backyard and patio with new grill and plenty of outdoor seating ☀Central AC for hot summer days! ☀ Hi-Speed WiFi and Roku Smart TV ☀ Screened in porch ☀ Beach umbrella, chairs, cooler, and beach cart in the shed for your enjoyment ☀ Primary suite with King Bed

Superhost

The living area features a blue sofa along with a stylish coffee table atop a colorful area rug. A fireplace is set against a decorative stone wall, and a large television is mounted above it. Dining space is visible in the background, along with bright natural light from the windows.

5 out of 5 average rating, 3 reviews

Lobster Trap: Beauport, Pavilion Beach, Downtown

Welcome to The Lobster Trap! BRAND NEW in July 2025! Located in historic Gloucester! When you step foot inside our doors, you'll feel right at home! From the spacious living & dining room areas to the cooks kitchen, it'll feel like you never left home! Our house features 3 very comfortable bedrooms with TV's in each room along with a pullout sofa in the living room. The outdoor gazebo is going to take your breath away with comfortable seating and screened in area!

4.99 out of 5 average rating, 142 reviews

The historic colonial house is framed by blooming trees, showcasing a classic exterior in dark blue with white accents. A stone walkway leads to the grand entrance, featuring large windows and an inviting front door. The surrounding greenery enhances the home's stately appearance.

Apartment in Salem

The Salem House | First floor 2 bedroom apartment

Historic 1850 built colonial house with restored exterior and interior odes to Doric order architecture. Originally built for a leather factory owner named Thomas Looby, The Salem house is now a beautiful opportunity to visit Salem in a distinguished space. Exactly one mile from downtown with off street parking, staying here allows being away from the craziness of the city center while intimately experiencing Salem by staying in a historic colonial home.

4.95 out of 5 average rating, 120 reviews

A cozy outdoor deck is presented with natural wood planks, leading to sliding glass doors framed by blue siding. Potted plants and decorative items are positioned near the entrance. A nearby patio chair adds to the inviting setting surrounded by landscaped greenery.

Condo in Gloucester

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!