
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.

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.

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!

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

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

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.

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.

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!

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.

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

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.

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
Apartment rentals with a patio

Hipster Basecamp | Modern • Fireplace • Parking

Private Studio Near Downtown & Ocean

Modern yet Historic Pad steps from Derby Street.2

Spacious & Luxury House |Overlooking Boston Harbor

2 BR w/parking in Spooky Salem

Spooky Salem Townhome: Downtown Roof Deck&Tiki Bar

2 bedrooms beach backyard Wi-fi& free parking

Danvers spacious apt near mall/ Hospital/Salem
House rentals with an outdoor patio

Stroll to SeaView/Beach; Great Yard

Charming waterfront home. Patio, AC, Shops, Dining

Oceanfront Home Rockport

Stone Cottage with meadow view

Large, Comfortable & Conveniently located Home

Cheerful 3-bedroom home with easy access to beach

Nothing Fancy Older Pet Friendly Home – near I-95

Ocean views! Welcome to Sea Breeze! Winter rates!
Condo rentals with a patio

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA

Spacious Luxury 3 BR, Spotless, W/D, Parking

Charming and Historic Apartment

The Salem Porch House

One bedroom apartment near Boston and Salem.

Stylish garden level studio with a private patio

Seacoast Getaway

Luxury Condo in Boston w/ backyard & parking
When is the best time to visit Gloucester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $275 CAD | $262 CAD | $273 CAD | $287 CAD | $352 CAD | $412 CAD | $463 CAD | $481 CAD | $400 CAD | $419 CAD | $343 CAD | $327 CAD |
| Avg. temp | -1 °C | 0 °C | 4 °C | 9 °C | 15 °C | 20 °C | 23 °C | 23 °C | 19 °C | 13 °C | 7 °C | 2 °C |
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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- Rentals with a patio Essex County
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