Holiday rentals with outdoor seating in Rockport

A spacious living area features a light grey sectional sofa accented with decorative pillows. A round coffee table sits at the center, adorned with candles and a decorative piece. Natural light floods the room through multiple windows, highlighting the warm wood flooring.

4.96 out of 5 average rating, 102 reviews

Balcony|KING Suite|Walk2Beach+Bearskin|Parking

Inquire about our winter rental rates! • 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 kitchen • Balcony with cafe seating • Ensuite bathroom with large Kohler soaking tub • Comfortable king and queen size memory foam beds • Convenient EV charging right across the street!

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.

4.99 out of 5 average rating, 155 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.

Superhost

An outdoor deck offers scenic harbor views, showcasing calm waters and a clear blue sky. The space features a railing and a table with chairs for relaxation, creating a welcoming environment for enjoying the coastal surroundings.

4.94 out of 5 average rating, 328 reviews

Harbor Retreat | Ocean View | Heart of Downtown

Discover Rockport's Harbor View Apartment! 🌊 This newly renovated 1-bedroom on the second level boasts stunning harbor views from a private deck. Steps from Bearskin Neck, enjoy proximity to unique shops 🛍️, fine dining 🍽️, and beaches 🏖️. Equipped with high-speed WiFi, a 55" Smart TV, and a Murphy couch. Perfect for experiencing Rockport's vibrant atmosphere. Note: Guests must climb stairs and the downtown location can be lively and noisy 🌆. Book your unforgettable seaside escape today! ⚓

The image captures a serene waterfront scene with comfortable Adirondack chairs arranged on a grassy area overlooking a calm harbor. The view includes a small dock with boats and a waterfront lined with rocky formations, creating a peaceful coastal ambiance.

4.98 out of 5 average rating, 250 reviews

Springtime waterviews in downtown Rockport

Come to Rockport this spring and stay at this renovated waterfront apartment in a historic home with onsite parking, yard and a private entrance. Our prime downtown location is steps from beaches, restaurants, coffee shops, live music, and shopping on Bearskin Neck. 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.

A welcoming living area features a comfortable gray sofa paired with a vibrant blue armchair. Natural light fills the space through multiple windows, highlighting the wooden ceiling beams. A dining table with two chairs sits nearby, complemented by decorative art and an accent rug.

4.98 out of 5 average rating, 109 reviews

Walk to Beach & Village at Historic Renovation

Are you dreaming of sun, sand and seafood?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.

4.99 out of 5 average rating, 149 reviews

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.

Guest house in Rockport

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!

4.98 out of 5 average rating, 123 reviews

A view of a waterfront building is framed by leafy tree branches. A staircase leads to a second-floor entrance. Brightly colored kayaks are lined up along the calm water's edge, with a wooden dock visible in the background.

Apartment in Rockport

Harbor Place - Airy hideaway over Rockport Harbor

Enjoy stunning views of Rockport Harbor and the Atlantic from Harbor Place, a breezy, quiet open-floorplan bnb on Tuna Wharf, steps from the galleries, shops and restaurants of bustling Bearskin Neck. You'll be within easy strolling distance of several beaches, the train station, the Shalin Liu Performance Center, kayak rentals, walking paths, parks and boat tours. Relax and enjoy the view, eat in or out, lounge on our private beach! Access to Harbor Place is via staircase.

4.99 out of 5 average rating, 210 reviews

A private deck overlooks Rockport Harbor, featuring two white Adirondack chairs with turquoise cushions. The calm water is dotted with boats, and the iconic Motif #1 is visible in the background, enhancing the coastal ambiance.

Apartment in Rockport

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!

A bright living area features large windows with views of a garden and ample natural light. A comfortable dark sofa and a plush chair are arranged around a glass coffee table on a colorful area rug. A wooden dresser and a small dining table add warmth to the space.

4.97 out of 5 average rating, 353 reviews

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.

4.88 out of 5 average rating, 271 reviews

An open living space features a comfortable sofa and a round coffee table set atop a patterned area rug. Light floods through large windows dressed in colorful curtains, illuminating an adjoining kitchen with bar seating.

Guest house in Rockport

Beautiful Apartment Near Town & Beaches

Sunny one bedroom apartment with seasonal views! Fully equipped kitchen, open floor plan, balcony and everything to make your stay pleasant and comfortable. The apartment is on the second floor of a garage. Some noise may come from the garage between 9am and 5pm. We're 1.5 miles from the heart of town and beaches, a 20 minute walk along the ocean. Also about 1.5 miles from the train station. Parking on site, off street is available for 1 car only.

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.

4.96 out of 5 average rating, 103 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.

An aerial view captures a spacious coastal home, surrounded by lush trees with changing leaves. The structure showcases a wraparound deck, and the sloped lot offers a rocky edge, enhancing the natural setting. Nearby residences are partially visible through the foliage.

4.94 out of 5 average rating, 188 reviews

Hidden Gem! Short term rental steps from 2 beaches

Hidden Gem! Short term seaside rental. Lovely 1 bed 1 bath unit located on private wooded property, steps away from 2 beaches. Private unit amenities include deck with gorgeous year round views of the Atlantic. Fully equipped kitchen, flat screen TV, WiFi, and everything to make your stay pleasant and comfortable. We're a 7 minute drive from downtown Rockport and Gloucester, a 7 minute walk to Cape Hedge and Long Beaches.

Popular amenities for outdoor seating rentals in Rockport

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.95 out of 5 average rating, 43 reviews

A sandy beach area is equipped with a gas grill, dining table, and lounge chairs under a large umbrella. Kayaks are neatly arranged along the shoreline, while a view of the calm water and distant boats is visible beneath the clear blue sky.

Home in Annisquam

Private Beach!

4.98 out of 5 average rating, 105 reviews

A traditional farmhouse is visible alongside a red barn, set against a backdrop of autumn foliage. The well-maintained lawn features neatly trimmed shrubs and trees, with the clear sky overhead highlighting the peaceful rural setting.

Home in Newton

Winnie's Place - Freshly Renovated 1800s Farmhouse

Two white rocking chairs sit invitingly along a stone walkway, facing a calm harbor. Reflections of colorful buildings and boats can be seen on the water's surface, framed by a vibrant sky during sunset.

4.97 out of 5 average rating, 89 reviews

Charming waterfront home. Patio, AC, Shops, Dining

4.98 out of 5 average rating, 112 reviews

A large tree with a broad canopy dominates the lush backyard, surrounded by greenery. The area features a stone border outlining a patch of grass, with glimpses of the landscape beyond, including wooded areas and a play structure in the distance.

Home in Danvers

Large, Comfortable & Conveniently located Home

4.78 out of 5 average rating, 224 reviews

A stone sign marked 'BEACHMONT' stands prominently at the entrance of a landscaped area. Surrounding features include a stone-paved pathway, a bench, and several tables. Lush greenery lines the background, providing a natural backdrop to the welcoming space.

Home in East Boston

Renovated Cozy City Getaway

4.81 out of 5 average rating, 220 reviews

The exterior of a two-story home is shown, featuring beige siding and multi-pane windows. A well-maintained front yard includes patches of grass and decorative bushes. A staircase leads to the front porch, with a fenced yard visible in the background, surrounded by trees for added privacy.

Home in Georgetown

Nothing Fancy Older Pet Friendly Home – near I-95

4.91 out of 5 average rating, 289 reviews

A cozy living area features a beige sofa, a green armchair, and a wooden coffee table with decorative centerpieces. A stylish rug adds texture to the floor. Walls are adorned with artwork and decorative pieces, while natural light filters through the windows.

Home in Lynn

Clean, spacious In-Law Suite -Near Everything

Home in Lakeside Marblehead

The living area features a dark blue sofa facing a mounted flat-screen TV. A wooden coffee table is positioned in front, surrounded by natural light from nearby windows. The white walls and sleek countertops contribute to a modern, open space. A minisplit unit is visible for climate control.

5 out of 5 average rating, 152 reviews

Seaside Cottage

Apartment rentals with outdoor seating

4.95 out of 5 average rating, 143 reviews

A spacious living area features a modern sectional couch and a grey accent chair, with an area rug adding warmth. Custom-made olive green bookshelves showcase a variety of decorative items. The open layout leads towards a staircase and kitchenette, enhancing the inviting atmosphere.

Flat in Peabody

Modern Apartment - Easy Commute to Salem/Boston

4.98 out of 5 average rating, 432 reviews

A well-lit sleeping area features a spacious bed adorned with soft linens and decorative pillows. Natural light fills the room from multiple windows, complemented by a cozy seating nook and shelving that adds a charming touch to the serene atmosphere.

Flat in Salem

Winter Island Retreat

4.95 out of 5 average rating, 111 reviews

A charming Victorian home is presented in a soft blue exterior, featuring large windows and decorative trim. Lush greenery surrounds the entrance, while a gravel pathway leads to the porch with inviting steps. A welcoming wreath adorns the front door, enhancing its friendly appeal.

Flat in Ipswich

Unit 1~Victorian Getaway Close to Beach & Downtown

4.97 out of 5 average rating, 145 reviews

A modern living area features a light-colored sofa adorned with decorative pillows and a natural wooden coffee table. A round mirror reflects light, while a small wooden side table and a potted plant add a touch of greenery. Soft ambient lighting enhances the soothing atmosphere.

Flat in Gloucester

Beautifully remodeled unit in heart of Gloucester

4.86 out of 5 average rating, 449 reviews

Flat in Beacon Hill

Beacon Hills Studio next to State house

4.99 out of 5 average rating, 198 reviews

Flat in Hampton Beach

Hampton Beach Island Path Unit 2 Open Year Round

4.91 out of 5 average rating, 142 reviews

Flat in Charlestown

Lux 2BR Apt w/ Pool and Gym

5 out of 5 average rating, 180 reviews

A comfortable living room is showcased with a blue sofa and two light-colored armchairs. A coffee table sits in the center, adorned with decorative items. Warm wood flooring complements the subtle hues of the walls, while soft lighting enhances the welcoming atmosphere.

Flat in Woburn

Charming 1 BR private entrance apt commuters dream

Apartment rentals with outdoor seating

Apartment in East Somerville

The living room is furnished with a brown leather sofa and a light-colored sectional, surrounded by multiple windows allowing natural light. A dark wooden coffee table is placed centrally, adorned with a decorative bowl. An accent chair and a white cabinet add to the room's functionality.

4.84 out of 5 average rating, 258 reviews

A Cozy 3BR Home Close To Train + Boston & Parking

4.97 out of 5 average rating, 326 reviews

A cozy living room features a gray sofa and a black leather chair, centered on a light-colored area rug. Two windows illuminate the space, complemented by light curtains. A wooden coffee table holds decorative items and a lamp, while a woven wall hanging adds texture.

Apartment in Salem

My Place - 2 Bedroom Condo with Parking

Apartment in Lakeside Marblehead

The living area features a mix of comfortable seating, including a floral-patterned sofa and a plaid armchair. A round coffee table sits atop a light blue area rug, and large windows allow natural light to fill the space, enhancing the cozy ambiance.

4.99 out of 5 average rating, 246 reviews

Harbor View Suite

4.96 out of 5 average rating, 125 reviews

Apartment in Beacon Hill

Charming and Historic Apartment

Apartment in Lakeside Marblehead

An open-concept living and dining area is showcased, featuring a wooden dining table with chairs, a comfortable sofa, and a flat-screen TV mounted on the wall. Natural light enters through multiple windows, enhancing the bright and airy feel of the space.

4.99 out of 5 average rating, 135 reviews

Samuel Tucker House - Downtown Luxury 2 Bed Condo

Superhost

A studio space features a spacious bed with a memory foam mattress and a queen pull-out sofa. A modern kitchen is visible, complemented by a dining area with high stools. Natural light enters through a window, while artwork adds visual interest to the walls.

Apartment in East Boston

4.83 out of 5 average rating, 306 reviews

Stylish garden level studio with a private patio

4.94 out of 5 average rating, 108 reviews

A spacious living area is highlighted by framed windows that provide ample natural light and offer views of the sky. A modern couch and an antique roll-top desk are present, accompanied by a cozy armchair. A decorative star design in the area rug adds a unique touch.

Apartment in Peabody

Peabody Penthouse Top of the World Sunset View