Holiday rentals with outdoor seating in Gloucester

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, 246 reviews

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.

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!

4.96 out of 5 average rating, 140 reviews

A spacious living area features large windows overlooking the water. A gray sofa and a blue armchair provide comfortable seating, while a wooden coffee table sits in front. A dining table with white chairs is positioned nearby, creating an inviting space for relaxation and meals.

Home in Gloucester

Views over Lobster Cove! Book spring/summer now

Booking spring and summer. Water views/access, sunsets above Lobster Cove on Washington St. Ideal for couple, NEW KING BED in master, queen in 2nd. Fast WiFi./TV. Not suitable for young children. Central A/C. 2nd fl unit large windows. Large living/dining/kitchen area. Comfy new mattresses, 100% cotton sheets,sound machines. Overlooks beautiful Lobster Cove and footbridge. Minutes walk to the village of Annisquam and Lighthouse Beach. Small deck. Swim/kayak out your door. Parking for one car

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.

Apartment in Gloucester

Beautifully remodeled unit in heart of Gloucester

Enjoy your stay in the heart of Gloucester close to everything this great town has to offer. This unit was completely remodeled in 2022. Two shorts blocks from Main Street in Gloucester and all of its wonderful restaurants and shops. Three blocks from the Beauport Hotel - perfect for wedding guests not staying at that location. This unit has new floors, countertops, appliances and fixtures and is freshly painted (no VOC paint). You will love this unit and its location for your visit.

4.97 out of 5 average rating, 146 reviews

The exterior view of the home reveals a modern wooden structure surrounded by lush greenery. A spacious deck extends from one side, while stone pathways weave through well-maintained gardens. Soft blue skies and gentle clouds create a serene atmosphere.

Home in Gloucester

Harbor View Walk to Beach & Town, 6Guests KingBeds

Spectacular Gloucester home on Cape Ann. Walk to Stage Fort Park & local beaches right across the street. Gloucester center is about 1 mile. On the way to town, walk by beaches & the park with waterfront tennis & bocce ball courts, plus a great water view playground and playing fields. Just beyond the park is famous Stacy Boulevard with the Fisherman's Memorial Monument along the waterfront. There are beautiful white sandy beaches (Good Harbor, Wingaersheek, Singing, & Crane's Beach).

4.97 out of 5 average rating, 353 reviews

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.

Home in 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.

4.93 out of 5 average rating, 113 reviews

A quaint stone cottage is surrounded by lush greenery and colorful flowers, with a well-maintained garden featuring clusters of purple blooms. The cottage's rustic charm is complemented by a sloped lawn and mature trees, creating a serene outdoor atmosphere.

Guesthouse in Gloucester

Plum Cove Cottage with king suite!

A quaint 1900's cottage Plum Cove beach is just 500 ft away! The full gourmet kitchen has granite counters and stainless steel appliances. There is also a spa shower, romantic king bedroom with maple spiral stairs and 3 skylights which provide amazing light throughout. Watch the spectacular sunsets voted one of the best in the world by National Geographic. This is the premier location to begin your exploration of Cape Ann. Beach umbrellas and chairs provided.

4.97 out of 5 average rating, 482 reviews

A charming log cabin is surrounded by lush greenery. Two miniature horses graze leisurely on the grass in front of the cabin, which features a covered porch and simple landscaping with flowers. Sunlight filters through the trees, highlighting the serene woodland setting.

Cabin in Rockport

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.

4.99 out of 5 average rating, 137 reviews

A spacious game room features a stylish hanging chair and a classic arcade machine in the background. Natural light illuminates the wood-paneled ceiling and bright walls, creating a welcoming space ideal for family fun or relaxation.

Condo in Gloucester

3BR Oceanfront Condo with decks

Have fun with the whole family at our stylish oceanfront condo. Capture exquisite sunrises and sunsets off of the decks overlooking the ocean. Spend time in the spacious arcade/game room with family and friends or listen to some smooth beats using our retro record player. Walk to downtown Gloucester where you will find a number of restaurants and bars or alternatively walk to exquisite beaches or parks all available steps from your front door.

4.96 out of 5 average rating, 103 reviews

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.

Home in Rockport

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, 187 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.

4.98 out of 5 average rating, 730 reviews

A cozy sleeping area features a queen bed with decorative pillows and a textured blanket. Two large windows provide natural light, while a charming quilted wall hanging adds character. A wooden dresser and seating area with wicker chairs enhance the inviting atmosphere.

Guest suite in Rockport

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 Gloucester outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday 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!

4.93 out of 5 average rating, 119 reviews

Aerial view of the spacious home reveals a wraparound deck with multiple seating areas, including shaded tables beneath umbrellas. The exterior features a light yellow façade complemented by large windows, surrounded by greenery that enhances the property's serene, secluded ambiance.

Home in Gloucester

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

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

4.97 out of 5 average rating, 112 reviews

The exterior of a colonial-style house is presented, featuring a symmetrical façade with a front porch, white railing, and wide steps leading to the entrance. A well-manicured lawn and garden flank the pathway, which guides toward the door. The vibrant greenery complements the home.

Home in Haverhill

Charming 4-Bedroom Colonial

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

4.98 out of 5 average rating, 109 reviews

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.

Home in Rockport

Walk to Beach and Shops at Historic Luxury Home

4.89 out of 5 average rating, 111 reviews

A serene sunset is captured over the horizon, casting warm hues of orange and pink across the sky. The silhouette of a distant landscape is visible along with the calm waters reflecting the evening light.

Home in Ipswich

Incredible Views of Ocean, River, Sunrise & Sunset

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

Apartment rentals with outdoor seating

Apartment in Lakeside Marblehead

A wooden deck is situated in the foreground, featuring a small seating area and an umbrella. Lush greenery, including tall evergreen trees and colorful shrubs, creates a natural backdrop. A stone pathway leads into the garden area, enhancing the tranquil outdoor space.

4.94 out of 5 average rating, 212 reviews

Two bedroom Apt with a deck

Superhost

An inviting living space features exposed wooden beams and a fireplace with a decorative mantle. A round dining table for four and comfortable seating are present. Two windows allow natural light to fill the room, providing views of the surroundings and enhancing the open layout.

Apartment in Salem

4.84 out of 5 average rating, 148 reviews

Historic House by the Gables

A cozy outdoor seating area overlooks the water, featuring two wicker chairs and a matching sofa arranged around a low table. A striped area rug anchors the space. The railing provides an unobstructed view of the rocky coastline and distant shoreline.

4.99 out of 5 average rating, 145 reviews

3 Bedroom Apartment with parking on Bearskin Neck

Apartment in Lakeside Marblehead

An inviting outdoor deck features a seating arrangement with matching dark wicker chairs and a lounge chair, surrounded by vibrant flower pots. The entrance is framed by a dark door, and large windows allow natural light to brighten the space.

4.96 out of 5 average rating, 311 reviews

Charming & Private Marblehead Suite

4.94 out of 5 average rating, 336 reviews

The entrance features a decorative purple door with a glass panel adorned with golden geometric designs. A brass door handle complements the door, while a small mailbox is mounted beside it. Pink flowers are visible in a planter, adding a touch of color to the entryway.

Apartment in Danvers

North shore getaway! Near Salem ,Gloucester

4.87 out of 5 average rating, 562 reviews

The exterior of a Victorian home is showcased, featuring a light-colored facade with decorative trim. A welcoming porch area is accented by potted plants, and steps lead up to a wooden front door flanked by tall windows. Lush greenery surrounds the property.

Apartment in Newtonville

Country Charm minutes from the Hub - 1st Floor Apt

4.94 out of 5 average rating, 723 reviews

The exterior of the apartment is framed by lush greenery, showcasing a well-maintained lawn. A winding pathway leads to a red door framed by a white porch. Surrounding flowers add color amidst the soft shade of nearby trees, creating a serene atmosphere.

Apartment in Beverly

Beverly Farms Apartment “Homeport”

4.89 out of 5 average rating, 101 reviews

A bright living space is furnished with a light-colored sofa and a wooden coffee table. A large wall-mounted TV is positioned above a light wood sideboard. A round mirror and a floor lamp add to the decor, while a dining area with a wooden table and benches is situated near a window adorned with natural light.

Apartment in Brighton

Luxury suite with room divider near downtown

Condo rentals with outdoor seating

4.92 out of 5 average rating, 172 reviews

A comfortable living area is highlighted by a modern sofa and minimalist armchairs. Natural light floods in from a window, illuminating a coffee table adorned with a book and decorative items. Shelves display plants and books, enhancing the cozy, inviting ambiance.

Condo in Davis Square

Bright & Spacious Home in Davis Sq, Somerville

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.

Condo in Rockport

Bearskin Neck Rockport ★ Amazing Views ★ Parking

4.96 out of 5 average rating, 124 reviews

Condo in Beacon Hill

Charming and Historic Apartment

Condo 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

Condo in Lakeside Marblehead

A comfortable living room features a soft gray sofa flanked by two armchairs. A round coffee table sits in the center, adorned with a decorative bowl. Natural light enters through a window adorned with white shutters, and a cozy rug enhances the inviting ambiance.

4.98 out of 5 average rating, 196 reviews

Harbor Hideaway

4.83 out of 5 average rating, 303 reviews

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.

Condo in East Boston

Stylish garden level studio with a private patio

4.92 out of 5 average rating, 196 reviews

An open living space features a modern gray sofa paired with a dark green accent chair. A round coffee table sits on a textured blue rug. Natural light enters through large windows, illuminating the dining area and kitchen with stainless steel appliances and wooden cabinets.

Condo in Waltham

New Super Modern 2 bed in Waltham