Vacation rentals with a patio in Winthrop

Apartment in South Boston

A spacious deck features a patio sectional sofa and a dining table with high chairs. Potted plants adorn the railing, adding greenery. The wooden deck is arranged for relaxation and outdoor dining, providing a comfortable retreat with ample seating.

4.94 out of 5 average rating, 113 reviews

2 BDR/2b- walk to Seaport & BCEC

We welcome you to stay at our stylish apartment in South Boston (Southie)! Located next to West Broadway, South Boston’s main road with plenty of restaurants, coffee shops, groceries, and boutique stores. Located walking distance to the Seaport District, Convention Center (BCEC), and our local Southie beaches. The space is ideal for travelling professionals, small families, couples, and those looking for a true neighborhood experience, tucked away just minutes from all the big city attractions.

4.97 out of 5 average rating, 106 reviews

A well-maintained outdoor patio area features two wooden chairs and a small table, surrounded by gravel paths and natural landscaping. String lights hang overhead, illuminating the space, while a grill is positioned nearby, all set against a backdrop of greenery and a colorful sunset.

Cottage in Hull

Retro New England Cottage - walk to the beach!

This is a private and peaceful beach retreat close to all the action. The one-bedroom cottage is the oldest in the neighborhood and full of retro charm. The house is within walking distance of Nantasket Beach and is set back from the road in a large, quiet yard. Don't worry about beach parking—the driveway is big enough to park two cars. Hull has plenty of restaurants and activities. Grab a post-swim ice cream in the summer, or drive to the beach and watch the waves roll in during the winter.

4.95 out of 5 average rating, 151 reviews

The image showcases a collage of four distinct areas within the unit. A cozy living space features a red sofa and coffee table, while a modern kitchen boasts stainless steel appliances and a spacious countertop. A serene sleeping area includes a large bed with a blue-and-white patterned backdrop. Lastly, a vibrant patio is visible through open doors, framed by greenery.

Condo in Gloucester

KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN

Looking for the perfect Gloucester retreat for your group or family? Look no further than this spacious and inviting 2-bedroom unit, ideal for families and groups seeking comfort, style, and ample room to relax. Step inside and be greeted by a bright and spacious living area, perfect for gathering together after a day of exploring all that Gloucester has to offer. With its comfortable furnishings and modern amenities, this unit is designed to provide you with the ultimate vacation experience.

4.82 out of 5 average rating, 153 reviews

A spacious outdoor terrace offers a scenic view, featuring several black woven chairs and a white table. The railing provides a sense of safety while allowing unobstructed sightlines of the surrounding area and distant landscape.

Apartment in East Boston

Stylish and Cozy at Revere Beach

Unwind in the stylish Studio apt in the heart of Revere. Enjoy the apartment all to yourself and your family. The city is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through Revere and the metro Boston region easily from this prime location with very close walking distance to Blue Line subway station and Revere Beach. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Full Bed ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Pool ✔ Gym

Cottage in Lakeside Marblehead

4.98 out of 5 average rating, 112 reviews

House with Pool, 4 Houses from Harbor, Fort Sewall

Marblehead Harbor is just 4 houses away from this beautiful antique home with a backyard pool in Old Town Marblehead. This quaint cottage is surrounded by a beautiful garden and is just steps away from The Barnacle Restaurant. Walkable to attractions like Fort Sewall, Fort Beach, Gas House Beach and local shops and restaurants. Car-free convenience in Old Town Marblehead. Perfect for couples or families seeking a charming and convenient getaway that offers off-street parking.

4.81 out of 5 average rating, 242 reviews

A spacious studio apartment features a king-size bed with colorful bedding and wall art. A futon is positioned near a circular coffee table on a patterned rug. Two small windows bring in natural light, while a ceiling fan ensures comfort.

Guest suite in Weymouth

Lovely studio on the coast! Beach close by!

Wonderful location located in north Weymouth. Quiet, Spacious studio apartment. Outdoor deck with patio furniture. Plenty of space for 3 guests max. - Walking distance to George lane beach & Wessagusset beach. - Convenience store, Pizza & Sandwich shop on our block. - 2 miles to Hingham shipyard - 5 miles to Nantasket beach - In between several commuter rail stations and across the street from a bus stop. - 4 miles to Quincy center - 30 minute drive to Boston!

4.95 out of 5 average rating, 178 reviews

An outdoor patio is shown, featuring wooden decking and shaded by large trees. Comfortable seating options include two chairs with red cushions. A variety of plants and flowers are arranged throughout the space, alongside a small decorative water feature and an American flag gently waving.

Apartment in Beverly

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

4.83 out of 5 average rating, 250 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

Enjoy your stay in this stylish East Boston garden level studio with a private back patio. It is centrally located near restaurants, the waterfront, a running & biking trail, the airport, public transportation, and it is 1 metro stop away from downtown Boston. The metro stop, Maverick, is a 4 minute walk! The studio is equipped with a king bed that has a memory foam mattress, a queen pull out sofa, and a fully equipped kitchen.

4.96 out of 5 average rating, 100 reviews

A charming outdoor space features comfortable lounge chairs set on a well-maintained lawn. A blue house with multiple levels is visible in the background, complemented by bright sunlight filtering through the leaves of a nearby tree.

Condo in Gloucester

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!

4.89 out of 5 average rating, 140 reviews

A spacious living area features a comfortable sofa, flanked by modern accent chairs. Large floor-to-ceiling windows provide abundant natural light and showcase views of the surrounding landscape. A stylish rug sits beneath the furniture, enhancing the room's contemporary design.

Apartment in Peabody

Executive Hotel Penthouse 1 Bedroom Residence

Take in the most beautiful sunsets over the Coast of the Northshore. Panoramic views from the 500 sq. ft deck. Spacious 1 bedroom Penthouse in apartment building. One full and one half bath creates privacy when entertaining. 9' celings and floor to ceiling windows make this unit bright, light and cheery. Laundry on site. Lots of restaurants within walking distance as is plenty of shopping and a luxury Health Club.

4.89 out of 5 average rating, 136 reviews

A modern kitchen features white cabinetry with a gray island and two black bar stools. Stainless steel appliances, including an oven and refrigerator, complement the light countertops. Pendant lights hang above the island, illuminating the space, while natural light streams through the window.

Condo in East Boston

Luxury Condo in Boston w/ backyard & parking

2 bedroom 1 bath condo with 1 parking spot, backyard, private outdoor deck and 2 private entrances. Located in East Boston, this condo is a 5 minute drive away from the airport and a 5 minute walk from Constitution Beach. This upscale suburb is a 10 minute drive from downtown Boston and a 10 minute walk from the T (Boston Subway). Located in a residential neighborhood, home to renown Italian and Latin restaurants.