
Holiday rentals with outdoor seating in Essex
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Essex
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Winter retreat & waterviews in downtown Rockport
Rockport is charming over the holidays with lights, music and shopping! This brand new waterfront apartment is in a historic home with onsite parking & a private entrance. Galleries, restaurants, coffee shops, live music and shopping on Bearskin Neck are steps away. Features full kitchen and bathroom with new applicances and fixtures. Living room has a loveseat, swivel chair, dining table, coffee table, roku TV, games, puzzles & books. Kitchen has a fridge, stove, oven, microwave and Keurig.

Lakefront cottage for a fun, relaxing getaway.
Enjoy a cozy stay in a lake front cottage. Located in Essex, on chebacco lake, this 3 bedroom, 1.5 bathroom home has everything you could need. Fully stocked kitchen, comfortable living space with wifi and a large TV, and a comfy couch overlooking the lake. We have a external monitor with a keyboard and mouse to set up a workstation if needed. A large deck and seasonal dock to hang out on. Close to the ocean if you get tired of the lake. It's an excellent home base on Boston's North Shore.

Unit 1~Victorian Getaway Close to Beach & Downtown
Holly House is a Victorian home within walking distance to Downtown Ipswich shops, restaurants, Historic High St & MBTA as well as Bialek Park, Willowdale State Forest, CSA Farms and many other amenities. Walk next door to the Historic 1640 Hart House for dinner or spend the day visiting the Crane Estate & Crane Beach! Unit 1 is on the first floor where you will enjoy minimal stairs (only to get in) & the convenience of 2 bedrooms, living room & fully equipped kitchen with sunny breakfast nook.

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.

Victorian Near Beaches, 2nd Floor of 2 Family Home
Great location for visiting Boston and the Northshore of MA. Close to Endicott & Gordon Colleges. Very safe residential neighborhood, only a short walk to 3 beaches, seaside park, quick market, steps to coffee shop. 4 miles from downtown Salem, MA, USA. Close to commuter rail inbound to Boston or out to Rockport/Gloucester. Sleeps 4, 2 bedrooms, 1 1/2 baths, fully equipped kitchen, dining rm, living rm, attic loft with platform bed, W/D, front porch for relaxing with private entrance & parking.

Charming 2 Bedroom Apartment in Historic Ipswich.
In the heart of historic downtown Ipswich, the John Brewer house has been a family home since 1680! This fully renovated apartment features many modern amenities, like hi-speed internet, 50" and 55" televisions with streaming channels. There is parking for two cars, and we are a short walk to Market Street, the commuter rail to Boston, a large park for children, and many fantastic local restaurants. Drive to Boston or Maine in 45 mins; Salem or Gloucester in 30 mins; Crane Beach in 10 mins!

Cozy place to relax! 14min to Salem - 25 to Boston
Due to your allergies, we are unable to Host any animals Private entrance-Basement - H 6' - entrance 5' 6" Relax in this calm, stylish space after a day of exploration! Perfect for travelers /work trips. Stay with US! I live on-site to ensure a safe and welcoming stay You will get to enjoy: - Salem MA - - Boston MA - Beaches - Beverly MA - Gloucester MA - Marblehead MA - Trails Our mattress is fairly firm, which can provide a very good night sleep! - Illegal activities will be reported -

Amazing Ocean View In-Law Apt.
Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

Beverly Farms Apartment “Homeport”
"Homeport" - A nautical themed apartment, nestled in the small coastal village of Beverly Farms. The village has cafes, restaurants, beaches and is nearby “Witch City” Salem MA. Homeport has a private entrance, den, two bedrooms, 1.5 baths with essential amenities and guest parking. The local area is famous for beaches, museums, galleries, eateries and many historic attractions. Explore the North Shore or take a commuter train to explore Boston, saving time and expense of driving.

French Flair "Pied a Terre" Cottage on the Marsh
Sunny cottage with marsh views, under 5 minute walk to town. Eat on the water in one of the many village restaurants, rent a kayak or paddle board. Go "down river" like a local! Shop the world renowned antique stores or enjoy the local beaches. There are many unique places to visit in Gloucester, Manchester, Rockport, Ipswich, Salem and of course Boston. There is a Visitor Manual for your convenience and we would be happy to answer questions that you might have.

The Solar Powered Dogtown Cabin at Applecart Farm
Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

Halibut Point State Park. Nature Lovers Retreat
"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.
Popular amenities for Essex outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Aerie, 2 king beds, large space, AC, 2 beaches!

Winnie's Place - Freshly Renovated 1800s Farmhouse

Quaint Little New Hampshire Lake House Getaway!

All New Private Country Setting (2 Level-No Share)

Newly renovated, spacious, clean, 3 bedroom home.

Charming Year Round Home, Plum Cove Cottage

Historic Luxury Renovation Walk to Town!

Private Sunny Apartment in hip Portsmouth West End
Apartment rentals with outdoor seating

Entire 1st floor apt in charming seaside Beverly

Light-Filled Luxury Apartment with View

Your Cozy 1 BR Apt & Relaxing Retreat

Downtown Derry, A Modern 2-bedroom apt.

Beautifully remodeled unit in heart of Gloucester

Hidden Gem! Short term rental steps from 2 beaches

2b apt loft downtown Ipswich

🎖The Ashmont Suite | Close to Subway + Downtown🎖
Condo rentals with outdoor seating

Family Home + Near Downtown + Cool Backyard!

Bearskin Neck Rockport ★ Amazing Views ★ Parking

Sunny Beach Studio Condo with Sunset View

Harbor View Suite

The Salem Porch House

Boston Rooftop Retreat

Badgers Island Condo- Sweeping Portsmouth Views #1

Luxurious beach house w/ harbor views & near beach
Quick stats about holiday rentals with outdoor seating in Essex

Total holiday rentals
Explore 20 holiday rentals in Essex

Nightly prices starting at
Essex holiday rentals start at $174 NZD per night before taxes and fees

Verified guest reviews
Over 1,340 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Essex holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Essex rentals

4.9 Average rating
Essex stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Rentals with a patio Essex
- Rentals with outdoor seating Essex County
- Rentals with outdoor seating Massachusetts
- Rentals with outdoor seating United States
- Hampton Beach
- Ogunquit Beach
- Fenway Park
- TD Garden
- Boston Common
- Harvard University
- Wells Beach
- Revere Beach
- Lynn Beach
- York Harbor Beach
- MIT Museum
- New England Aquarium
- Long Sands Beach
- Freedom Trail
- Good Harbor Beach
- Canobie Lake Park
- Duxbury Beach
- Crane Beach
- Museum of Fine Arts
- Jenness State Beach
- Quincy Market
- Rye North Beach
- Prudential Center
- North Hampton Beach




