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

Harborside Oasis | Harbor View | Heart of Downtown
Step into Coastal Bliss at Our Rockport Apartment! 🌊🏠 Perfectly positioned just steps from Bearskin Neck, immerse yourself in unique shops 🛍️, exquisite dining 🍽️, and serene beaches 🏖️. Revel in the spectacular views of iconic Motif Number 1 from your balcony, enjoy high-speed WiFi, and a 55" Smart TV in a fully stocked kitchen. Ideal for soaking in Rockport's vibrant yet relaxing atmosphere. Note: Requires climbing stairs and can get noisy! Book your unforgettable seaside retreat today! ⚓

Waterfront Escape! In-town with onsite parking
Brand new waterfront apartment in historic home with onsite parking & private entrance in the heart of town. Views and access to historic harbor from private deck. Beaches, 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.

Walk to Beach/Town at Historic Renovation
Come visit a very special home this winter! Stay at the 1767 Tuck House, where historic charm meets quintessential New England luxury! This is the perfect home for groups. Steps to the beach, shops, restaurants and arts. Home offers the privacy of boutique hotel with modern comforts: plush Casper mattresses, AC, 4K TV, laundry, heated floors, quartz counters, new appliances, 3BR, 3 Full Baths, 2 Kitchens, 2 Decks, Private Entries. A true Rockport gem, we promise a special stay.

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.

3 Bedroom Apartment with parking on Bearskin Neck
Built in 1822, the Sound House is conveniently located on Bearskin Neck. The upstairs apartment is renovated with brand new oak floors, new bathrooms, and updated living area. The unit features 3 bedrooms and 2 full bathrooms, with laundry as well as 3 parking spaces in the back of the building. The kitchen includes cooking utensils, with an electric grill and butane burner for outdoor cooking on the new deck overlooking Cape Ann. Enjoy Rockport while creating new memories at the Sound House!

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!

2BR/2.5Bath|KING Suite|Walk2Beach+Bearskin|Parking
• Steps to Front Beach, Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu • Private off street parking spots for 2 cars • High Speed Wi-Fi • 10 minute walk from commuter rail to Boston • Smart TV equipped to stream all your favorites • Fully stocked and renovated kitchen • Balcony with cafe seating for outdoor meals • Ensuite bathroom with large Kohler soaking tub • Comfortable king and queen size memory foam beds • Convenient EV charging right across the street!

Historic Rockport Large Suite, Entire Third Floor.
This 3rd floor suite is the entire top floor of a Historic home. Jack and Jill bathroom. Enjoy a short walk to Old Garden Beach , Front beach, Shalin Liu Performance Center and all of downtown shops, restaurants and art galleries. You will enter your suite via a keyless door up a private “good morning” staircase. Extra bedroom available- A second bedroom off of your private staircase on the second floor landing. Message for pricing. This is not included if no prior arrangement.

Bearskin Neck Rockport ★ Amazing Views ★ Parking
From the deck of this New England vacation retreat enjoy amazing views of Rockport Harbor and the iconic Motif #1. Steps from delightful shops, restaurants, and ice cream/coffee, this recently updated 1-bedroom, 1-bathroom condo with rare, on-site parking is located in the heart of Rockport on Bearskin Neck. Enjoy beautiful ocean breezes with coffee or cocktails on the deck of this sweet beach retreat nestled on the N.E. coast. Come fall in love with charming Rockport!

Charming Toe-Hold, A Short Walk to Town and Beach
Toe-Hold is a wonderful year-round 1846 home with plenty of rooms, reading nooks and quiet spaces for family and friends of all backgrounds to eat and play together. The gorgeous beaches and picturesque downtown, great restaurants, art galleries and shops for the whole family, are within 10-15 minute walk. Rockport is one of the oldest art colonies in the US, and home to generations of fishermen. Day trips by car or train to Boston and other beautiful historic towns.

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.

Spectacular Views of Rockport Harbor.
The Mooring Stone Guest House is located directly on Rockport Harbor across from Motif #1 & Bearskin Neck. Enjoy your harbor-facing suite with private bath & patio. Private entrance affords you freedom to come & go at will. Fabulous, interesting & ever-changing views make for great photo opportunities & will keep you entertained in this quaint New England seaside village. Self- Check-In (how to info given near to occupancy date).
Popular amenities for Rockport outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Spacious waterfront free parking &Wi-fi

Winnie's Place - Freshly Renovated 1800s Farmhouse

“Salty Girl” Plum Island, MA

A water view slice of heaven at Pepperrell Cove

Charming waterfront home. Patio, AC, Shops, Dining

Modern farmhouse with all the comforts of home!

Gloucester Beach House, near Good Harbor Beach!

Pirates Hideaway - Sanctuary on the Marsh
Apartment rentals with outdoor seating

Private apartment 10 min to Salem!

Mid Town Marblehead 1 B/R Pvt. Wing w/Own Entrance

Modern Apartment - Easy Commute to Salem/Boston

My Dream house with views of the marsh and sunset

Winter Island Retreat

Unit 2~Garden Getaway Close to Beach & Downtown

Beverly Farms Apartment “Homeport”

Goose Point Getaway (a boutique AirBnB experience)
Condo rentals with outdoor seating

My Place - 2 Bedroom Condo with Parking

Sunny Beach Studio Condo with Sunset View

Cozy Entire Unit Condo close to UMASS Lowell

Harbor View Suite

Beachfront Getaway

The Salem Porch House

Samuel Tucker House - Downtown Luxury 2 Bed Condo

Summer bliss in our oceanfront 2BR condo awaits!
Quick stats about holiday rentals with outdoor seating in Rockport
Total rentals
180 properties
Nightly prices starting at
$46 AUD before taxes and fees
Total number of reviews
10K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Destinations to explore
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- Rentals with outdoor seating Essex County
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- Rentals with outdoor seating United States
- Hampton Beach
- Ogunquit Beach
- Fenway Park
- Wells Beach
- Boston Common
- TD Garden
- Harvard University
- Revere Beach
- Lynn Beach
- York Harbor Beach
- Duxbury Beach
- Long Sands Beach
- New England Aquarium
- Good Harbor Beach
- Canobie Lake Park
- MIT Museum
- Freedom Trail
- Crane Beach
- Faneuil Hall Marketplace
- Museum of Fine Arts, Boston
- Jenness State Beach
- North Hampton Beach
- Rye North Beach
- Quincy Market