Vacation rentals with a patio in Gloucester

Find and book unique accommodations with an outdoor patio on Airbnb

Top-rated accommodations with an outdoor patio in Gloucester

Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.

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Top guest favourite
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
4.99 out of 5 average rating, 156 reviews

4 Bed 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.

Top guest favourite
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
4.99 out of 5 average rating, 149 reviews

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!

Guest favourite
A modern kitchen features a spacious quartz countertop with a view through three large windows overlooking Sandy Bay. The cabinetry is a deep blue, complemented by decorative items and a stainless-steel sink. Natural light brightens the area, enhancing the open and airy feel.
Apartment in Rockport
4.88 out of 5 average rating, 41 reviews

Rare Waterfront Luxury Penthouse|Bearskin Neck

☀ Waterfront deck with lots of outdoor seating ☀ 1 bedroom, 2 full size sleeper sofas ☀ Renovated modern bathroom with spacious tiled shower ☀ Modern and well-equipped kitchen with large island that seats 6 ☀Central AC for hot summer days ☀ Hi-Speed WiFi, 2 large Smart TVs, and Sonos speaker for entertainment ☀ Washer/dryer in unit ☀ Rare California King Bed ☀ Directly next to the famous Shalin-liu theater and steps away from scenic downtown Rockport

Top guest favourite
A functional kitchen is equipped with wooden cabinets and modern appliances. A stove with an oven is positioned next to a microwave and kettle. Natural light enters through a window adorned with sheer curtains, pairing with decorative items on the countertop.
Apartment in Beverly
4.95 out of 5 average rating, 221 reviews

Entire 1st floor apt in charming seaside Beverly

Enjoy a stylish experience at this centrally-located place. Easy access to downtown Beverly, Salem, local beaches, and commuter rail to Boston. Apartment features a fully furnished living room, bedroom, and kitchen, along with extra amenities including a/c, 𝖶𝗂𝖥𝗂, cable, front and back porch, and outdoor fireplace and patio. Walking distance to all that downtown Beverly has to offer One train stop or 5 minute drive to downtown Salem

Top guest favourite
A cozy family room is filled with natural light from multiple large windows, offering views of the outside. A comfortable gray sofa and two white chairs are arranged around a glass coffee table. Decorative pillows and a fresh flower arrangement enhance the inviting setting.
Home in Rockport
4.96 out of 5 average rating, 106 reviews

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.

Top guest favourite
A light-filled living area features a soft blue sofa adorned with cushions in vibrant colors. Large windows offer views of the serene water outside, while greenery and a stylish glass coffee table enhance the inviting atmosphere.
Guest suite in Beverly
4.99 out of 5 average rating, 103 reviews

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.

Top guest favourite
The living area features exposed brick walls and wooden beams, creating a modern yet cozy ambiance. A large leather sectional couch offers ample seating, while a 75" TV is mounted on the wall. Natural light fills the space through multiple windows.
Apartment in Newburyport
4.98 out of 5 average rating, 266 reviews

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.

Guest favourite
Condo in East Gloucester
4.95 out of 5 average rating, 139 reviews

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!

Guest favourite
The outdoor patio features a dining table with four chairs and a grill. A large umbrella provides shade, while greenery is visible in the background. The deck is furnished with light-colored flooring, offering an inviting space for outdoor gatherings.
Apartment in Ipswich
4.82 out of 5 average rating, 190 reviews

2b apt loft downtown Ipswich

When you get in to this apt/loft you will be amazed by the comfort and cozy set up. This unit is located downtown Ipswich on the third floor with a beautiful view where you can enjoy sunsets and have a place to hang out. NOT RECOMMENDED for elderly people because of the stairs. there are three sets of stairs, also if you are traveling with young children or toddlers need to be aware of the height and the whereabouts.

Top guest favourite
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.
Cottage in Marblehead
4.99 out of 5 average rating, 147 reviews

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

Guest favourite
The open living space features a modern kitchen equipped with stainless steel appliances and a white countertop. Two upholstered stools are positioned at the counter. A light-furnished sofa, adorned with decorative pillows, complements the neutral tones, while natural light streams in through a window.
Tiny homes in East Gloucester
5 out of 5 average rating, 22 reviews

Smith Cove Cottgage

Escape to the charming Smith Cove Cottage, a beautifully restored boutique, haven situated at the gateway to historic Rocky Neck in East Gloucester, just steps from the picturesque Smith Cove and the Outer Harbor. This seaside gem has been meticulously renovated to seamlessly blend modern comforts with traditional charm, offering the perfect location for relaxation and adventure.

Top guest favourite
Loft in Gloucester
4.97 out of 5 average rating, 206 reviews

Downtown, Shops, Beach, Deck, Close to Salem

Charming Downtown Gloucester Loft 🏙️🌊 Escape to this stylish and spacious loft at 278 Main St, Unit B, Gloucester, MA 01930, located in the heart of downtown Gloucester. Perfect for couples, friends, or small families, you’ll be just steps from restaurants, boutique shops, and the scenic Good Harbor Beach—the ideal blend of city and coastal charm. 🛍️☀️

Popular amenities for Gloucester accommodations with an outdoor patio

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Quick stats about vacation rentals with a patio in Gloucester

  • Total vacation rentals

    Explore 390 vacation rentals in Gloucester

  • Nightly prices starting at

    Gloucester vacation rentals start at $82 CAD per night before taxes and fees

  • Verified guest reviews

    Over 22,310 verified reviews to help you choose

  • Family-friendly vacation rentals

    280 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 110 rentals that welcome pets

  • Rentals with dedicated workspaces

    200 properties have a dedicated workspace

  • Wifi availability

    380 of Gloucester vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Gloucester rentals

  • 4.9 Average rating

    Gloucester stays are highly rated by guests—averaging 4.9 out of 5!

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