
Holiday rentals with a patio in Gloucester
Find and book unique rentals with patio on Airbnb
Top-rated rentals with patio in Gloucester
Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

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.

Peabody Penthouse Top of the World Sunset View
Enjoy sunrise/sunset panoramic view from the new 6th floor Penthouse Sanctuary, the highest point in Peabody! This thoughtfully decorated spacious Penthouse open floor plan is a place to retreat, recharge, write, envision, and to enjoy the best of life. A walk away from the NS Mall/Borders Books where the Logan Express arrives. Also a mile away are the running trails, lovely ponds and apple picking at the city run Brooksby farm and six miles away from historic Salem. You will love it here!

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.

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.

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!

The Salem Porch House
The Salem Porch House is a beautiful, comfortable one bedroom condo and relaxing porch with views of the Salem Common on a residential side street. The condo has a spacious primary bedroom with a king bed, full eat in kitchen with a farmhouse table, small bathroom with a sunken claw foot shower/tub and a peaceful living room with a queen bed for additional guests. The space is ideally located right downtown... everything is walking distance and many things literally 1-5 minutes away!

The Artist Suite by Toi Moi
Welcome to Toi Moi's latest addition to AirBnb. This art-filled and chic suite with its own entrance and parking area blends influences from the Wabi-sabi philosophy, minimalist design, and old world treasures collected from our trips to create a unique aesthetic experience unavailable anywhere else on the North Shore. The Artist Suite is attached to our private home deep in the woods, creating a space for the solo traveler or romantic couple looking for serenity and inspiration.

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

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.

Beacon Hills Studio next to State house 3
Come stay at our lovely studio in the heart of Boston's most desirable neighborhood, Beacon Hill! Whether you want to walk the Freedom Trail, or shop on Newbury St, Surrounded by brownstones, coffee shops, and locals, you’ll feel right at home in this community. Steps away from the State House, MGH, and the Boston Common, You could not be more centrally located to take in all the city has to offer.Take it easy at this unique and tranquil getaway.

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

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!
Popular amenities for rentals with patio in Gloucester
Flat rentals with a patio

Peaceful suite in Boston with city views

Hipster Basecamp | fireplace • views • parking

Your Cozy 1 BR Apt & Relaxing Retreat

City Loft | Group Getaway | King Downtown Location

2b apt loft downtown Ipswich

Backyard Beachfront 2 bedrooms Wi-fi& free parking

Newly renovated apartment close to downtown.

Penthouse w/Private Deck| Panoramic Views |Sunsets
House rentals with a patio

Northridge View

Entire Apartment in Stoneham

Chic Coastal Retreat

Oceanfront Home Rockport

Stone Cottage with meadow view

Residential home ▪ Billerica ▪ quiet, clean & cozy

The Nest | A peaceful retreat in the city

Sea Forever - Oceanfront Home in Nahant!
Apartment rentals with a patio

Tufts 2 Bed + Office - Free Parking

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

South End 1800sqft 2BR Audiophile Paradise

Charming and Historic Apartment

Stunning South End 1BR - private roof deck

One bedroom apartment near Boston and Salem.

Stylish garden level studio with a private patio

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 | $259 SGD | $248 SGD | $258 SGD | $271 SGD | $332 SGD | $389 SGD | $421 SGD | $447 SGD | $368 SGD | $382 SGD | $303 SGD | $266 SGD |
| 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 holiday rentals with a patio in Gloucester

Total holiday rentals
Explore 390 holiday rentals in Gloucester

Nightly prices starting at
Gloucester holiday rentals start at $117 SGD per night before taxes and fees

Verified guest reviews
Over 21,530 verified reviews to help you choose

Family-friendly holiday rentals
280 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 110 rentals that welcome pets

Rentals with dedicated workspaces
200 properties have a dedicated workspace

Wifi availability
390 of Gloucester holiday 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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- Quebec City Holiday rentals
- The Hamptons Holiday rentals
- Rentals with a fireplace Gloucester
- Rentals with outdoor seating Gloucester
- Beachfront rentals Gloucester
- Rentals with a firepit Gloucester
- Apartment rentals Gloucester
- Rentals with a washing machine and dryer Gloucester
- Private suite rentals Gloucester
- Rentals with breakfast Gloucester
- Pet-friendly rentals Gloucester
- Rentals with a kayak Gloucester
- Waterfront rentals Gloucester
- Family-friendly rentals Gloucester
- Fitness-friendly rentals Gloucester
- Rentals with an EV charger Gloucester
- Flat rentals Gloucester
- Rentals with beach access Gloucester
- House rentals Gloucester
- Rentals with a patio Essex County
- Rentals with a patio Massachusetts
- Rentals with a patio United States
- Hampton Beach
- Ogunquit Beach
- Fenway Park
- Boston Common
- Wells Beach
- TD Garden
- Harvard University
- Revere Beach
- Lynn Beach
- York Harbor Beach
- New England Aquarium
- Duxbury Beach
- Long Sands Beach
- Good Harbor Beach
- Freedom Trail
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Museum of Fine Arts, Boston
- Jenness State Beach
- Quincy Market
- Rye North Beach
- North Hampton Beach
- Prudential Center