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Vacation rentals with outdoor seating in Winthrop

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Winthrop outdoor seating rentals

House rentals with outdoor seating

Top guest favorite
The exterior of the home showcases a light gray facade with dark shutters and a steeply pitched roof. A wooden entryway is visible, leading to the front door. Surrounding greenery is neatly arranged, complemented by a clear blue sky.
Home in Rockport
5 out of 5 average rating, 14 reviews

Adorable renovated house, steps from Front Beach

EmilyRating, 5 stars8 months ago
Gretchen’s house is a charming, two-story one on a very nice and quiet little street. The furnishings are pretty and tasteful, and there is comfortable living room furniture, as well an excellent beds and pillows. Our favorite thing was its location, within very easy walking distance from a gorgeous park and beach. Downtown was also reachable via a short walk. We did some of our own cooking and found everything we needed. Gretchen was an especially nice and responsive hostess. If we were lucky enough to get to Rockport again, I would want to stay there.
Superhost
The outdoor space features a luxurious hot tub illuminated by soft lighting, surrounded by seating and dining areas under wide umbrellas. A grill and outdoor kitchen are visible, with string lights providing a warm ambiance to the entire area.
Home in Plymouth
4.85 out of 5 average rating, 13 reviews

Downtown Luxury Villa on the Plymouth Waterfront

JaredRating, 5 stars6 months ago
Perfect location for everything you might want to do in Plymouth. Great restaurants are a short walk away, and so is the beach . The home is perfect—great private patio, a hot tub, outdoor kitchen, perfect for a quiet getaway or with guests. Keeping this place on my wishlist for future visits.
Superhost
A cozy outdoor space features a stone fire pit surrounded by a paved patio. A wooden bench sits nearby, with a barbecue grill positioned to the left. Lush, manicured shrubs and small trees frame the area, providing a sense of privacy and tranquility.
Home in Wayland
4.78 out of 5 average rating, 489 reviews

Tiny house experience steps from the water!

DemetriusRating, 5 stars1 month ago
Beautiful getaway right outside of Boston in a lovely town I would recommend Dean’s place to anyone visiting Boston that did not want to stay in the busy city but fairly close. The home was a unique with a great small back yard, parking, fire pit this tiny home is perfecto.
Guest favorite
A modern two-story house is surrounded by a spacious yard, featuring a well-maintained lawn and trimmed evergreen shrubs. A gravel driveway leads to the property, while trees provide a natural backdrop. The clear blue sky and gentle cloud formations add to the outdoor atmosphere.
Home in Reading
4.94 out of 5 average rating, 64 reviews

Charming Home in Reading with a Large Yard

VictorRating, 5 stars2 weeks ago
We were in the area for work. Peter’s property was homey and comfortable. Peter was also a great host. We highly recommend staying here
Top guest favorite
A charming two-story house features a covered front porch with wooden railings and rocking chairs. Lush greenery surrounds the entrance, while a paved pathway leads to the front door. The exterior showcases a rustic brown color, complemented by dark shutters and a steep roof.
Home in Wrentham
4.88 out of 5 average rating, 106 reviews

Backyard Oasis with Hot Tub

JasonRating, 5 stars1 day ago
Went for post malone concert at gilette stadium. Super conveniently located, spa was super nice. Pool was fresh. Beautiful home and space all in all!
Superhost
The exterior of a two-story duplex features a light beige facade and welcoming entryway. A parked vehicle is seen in the driveway, with two small chairs placed nearby. A decorative wreath adorns the door, and an American flag flutters gently in the breeze.
Home in Marshfield
4.86 out of 5 average rating, 14 reviews

"The Fieldstone Beach House"

JenniferRating, 5 stars8 months ago
Nice place with everything we needed in it. Andreas was super great. We went in a fishing charter and he let us borrow a cooler for our trip. The showers were amazing. The outside sitting area with a fire pit was one of the greatest features. We are a cooking family and although there were two cooking areas to stay together and cook it was a tight fit. What we got for the price was a really good deal.
Top guest favorite
An outdoor hot tub is positioned on a deck, surrounded by a white privacy fence. The water glows in soft blue under the night sky, creating a serene ambiance. Steps lead down to a landscaped area with stone features.
Home in Plymouth
4.97 out of 5 average rating, 145 reviews

The Mojito House with Hot Tub, Arcade and Theater.

AnaRating, 5 stars2 weeks ago
The Mojito House was perfect for our needs. Super spacious, clean and homey. It is so much more than what the pictures portray. Excellent choice for families of all ages. The game room was awesome!!
Guest favorite
A charming cape house is viewed from the street, featuring a covered porch with white railings. Large windows allow natural light to fill the interior. The surrounding yard is flat and grassy, bordered by trees that provide shade in a peaceful neighborhood.
Home in Gloucester
4.91 out of 5 average rating, 126 reviews

Gloucester Beach House, near Good Harbor Beach!

SuzanneRating, 5 stars6 days ago
Cozy & comfortable house & convenient location for our visit to Gloucester for family wedding. Loved that it was walkable to market for coffee or lunch AND the beach. Weather not great while we were there but lots of games, puzzles, etc in the house to keep us entertained. Diane was very attentive, offered early check-in which we took advantage of. Highly recommend.

Apartment rentals with outdoor seating

Top guest favorite
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.
Apartment in Lakeside Marblehead
4.94 out of 5 average rating, 194 reviews

Two bedroom Apt with a deck

CindieRating, 5 stars2 weeks ago
This was the cutest place! We all loved the garden space. The deck was very inviting. Rhona was kind enough to leave English muffins and butter for us. The selection of tea was fabulous! The bouquet and house plants made it feel very homey. There was an area close by that had a convenience store, a Dunkin Donuts, and a few decent restaurants. We would stay here again if we come back.
Top guest favorite
A functional kitchen is equipped with wooden cabinets and modern appliances. A stove with an oven is positioned next to a microwave and kettle. Natural light enters through a window adorned with sheer curtains, pairing with decorative items on the countertop.
Apartment in Beverly
4.95 out of 5 average rating, 183 reviews

Entire 1st floor apt in charming seaside Beverly

RodRating, 5 stars2 weeks ago
One of the very best Airbnb‘s I’ve ever stayed at! The place was clean and extremely well stocked. It was comfortable and the horse were very friendly! Fresh baked goods and fruit awaited us when we arrived! Even the refrigerator offered bottled water and other refreshment! Location had great restaurants close by and Salem was just over the bridge. We were there for our daughter‘s graduation from Endicott College, and it worked out perfectly! We can’t wait to come back and stay again!
Top guest favorite
An inviting living area features a grey recliner and a brown sofa, arranged on an orange and grey patterned rug. A large TV is mounted on the wall, while a dining table is visible in the background surrounded by chairs. Natural light filters through the windows.
Apartment in Medford
4.99 out of 5 average rating, 138 reviews

Couples Retreat - Apt in Charming Colonial Home

DanRating, 5 stars1 week ago
We have stayed in many Airbnb properties. This one may have been the best overall experience. The place was clean, well furnished, and above all, Lisa thought of everything you could need for your stay. There was a first aid kit, extra toiletries, and a lot of breakfast/snack foods furnished. We felt so comfortable and welcome. There were a few neighborhood restaurants in easy walking distance that were great. We highly recommend this property. They "do it" really well!
Top guest favorite
A private backyard features landscaped areas with green lawn and mulch, patio stones, and seating options. Comfortable blue chairs sit under an umbrella, adjacent to a wooden dining set. A fire pit area complements the space, surrounded by lush greenery and flowering plants.
Apartment in Plymouth
4.97 out of 5 average rating, 119 reviews

Downtown Backyard Oasis

LianaRating, 5 stars4 weeks ago
Great place to stay while in Plymouth! Erin was communicative and the place was just as pictured and described. Best of all it was walking distance to all attractions in the town.
Superhost
A private wrap-around porch is shown, featuring a wooden dining table with matching chairs. Sunlight filters through, illuminating the surrounding neighborhood with cozy homes and greenery visible in the background. The space is complemented by a decorative plant on the table.
Apartment in Swampscott
4.86 out of 5 average rating, 114 reviews

Ocean views, Large Deck, Grill, Kid/Dog Friendly

JenniferRating, 5 stars2 days ago
This place is an amazing find in a lovely area of Swampscott. Their home is situated right across the street from the water, and it’s less than a five minute walk to many area restaurants and shops. Ryan was very accommodating with a last-minute booking, he sent clear instructions so check-in was easy. His home is beautiful and very spacious - and the listing photos are an exact representation of their home. Ryan was also extremely responsive to any questions, and checked in during our stay to ensure we had everything we needed and even provided recommendations for places to go. I do hope to return for another retreat stay as there were many places to walk and explore and we didn’t cover it all in our time there. This is also very close to Salem/Boston but is tucked away from busy city and everyone in the area was friendly. I highly recommend booking a stay in their home, and I look forward to staying there again in the future.
Guest favorite
A modern dining area features a glass-top table surrounded by four black chairs, positioned over a decorative rug. A colorful wall art piece is displayed nearby, and an electric fireplace adds warmth to the space. Light-colored walls and flooring enhance the ambiance.
Apartment in Quincy
4.95 out of 5 average rating, 102 reviews

“Very Modern Apartment” Dedicated Driveway Parking

LindaRating, 5 stars2 weeks ago
My family and I stayed at Chau’s place for a few days while visiting relatives in Boston . We had a great experience; the unit was clean, spacious and fully stocked with all the essentials for a comfortable stay. The host was helpful and responsive and the surrounding neighborhood was quiet and peaceful. We would highly recommend this Airbnb rental for everyone looking for a convenient and safe place to stay in the Boston area.
Guest favorite
A bright bedroom features a spacious bed with light bedding and decorative pillows. Two large windows allow natural light to illuminate the room. A cozy armchair and a nightstand with lamps enhance the comfort, while a subtle area rug adds warmth to the hardwood floor.
Apartment in South Boston
4.93 out of 5 average rating, 121 reviews

2 BDR/2b- walk to Seaport & BCEC

LisaRating, 5 stars1 week ago
Lucio’s place was perfect for our weekend getaway! It was super clean and tidy, well stocked and so comfortable. It’s in a cute neighbourhood and we were within walking distance of some wonderful restaurants and public transit. Lucio was incredibly helpful with travel and parking tips making our stay absolutely perfect! We would definitely return next time we’re in the area!
Superhost
A spacious kitchen is defined by rich wooden cabinetry and countertops, featuring a stainless steel refrigerator and microwave. A wooden dining table with multiple chairs is arranged nearby. Soft lighting highlights the tiled floor and decorative backsplash, creating a functional cooking space.
Apartment in Dorchester
4.87 out of 5 average rating, 111 reviews

Rare 3.5 bed apt, super location Boston, +parking

YlRating, 5 stars2 weeks ago
I'm glad to be able to book such a good value for money house in Boston. The stay is very good, fully equipped, especially satisfied with the bedroom, bedding and mattress are all very comfortable.The location is 14 minutes walk from the subway, a bit far.

Condo rentals with outdoor seating

Guest favorite
A spacious living area is featured, furnished with a large, cream-colored sectional sofa. A wooden coffee table sits in the center, surrounded by natural light filtering through multiple windows adorned with sheer curtains. Open beams and a modern ceiling fan are visible above.
Condo in Lakeside Marblehead
4.94 out of 5 average rating, 123 reviews

Luxury 2 Bed, 2 Bath, Plus Loft, Modern Condo

JoshuaRating, 5 stars5 months ago
Our family really enjoyed our long weekend at Donald’s place. The location is great, right in the middle of Marblehead, walkable to old town and the various shops and restaurants that dot the area— a great base for visiting friends and family on the north shore. We’ll definitely look to stay here again if available the next time we’re in the area.
Superhost
A bright living area is highlighted by a circular dining table surrounded by four chairs. A large round mirror above a white fireplace reflects the light. Warm wooden floors contrast with the cream walls, accentuated by subtle decor elements and natural light from nearby windows.
Condo in Downtown Boston
4.88 out of 5 average rating, 113 reviews

Condo in downtown Boston

SusanRating, 5 stars2 weeks ago
This was such a charming place in a wonderful location. Griffin and Carolyn were responsive and took really good care of us. They are great hosts who we highly recommend and would book with again!
Top guest favorite
A modern living area features a black leather sofa paired with decorative pillows. A white area rug lies beneath a coffee table, complemented by an accent chair with a geometric pattern. Natural light filters through the two windows, creating a bright and inviting space.
Condo in Cambridge
4.92 out of 5 average rating, 773 reviews

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

EileenRating, 5 stars1 week ago
Dan was such a wonderful host. He was extremely helpful and responded quickly to our questions. The home is beautiful and very comfortable and the little touches such as snacks and beverages he left were much appreciated. I would highly recommend the hosts and the accommodations.
Guest favorite
A cozy outdoor patio features two bright red Adirondack chairs and a white circular table. The table holds two bowls of snacks and a glass of orange beverage. A backdrop of greenery creates a serene setting, enhancing relaxation.
Condo in Gloucester
4.96 out of 5 average rating, 156 reviews

KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN

SteveRating, 5 stars3 days ago
What more can I say that hasn't already been said by other guests? The place was perfect for our 35th anniversary get-a-way. Darryl was so on top of things. We had a question and it was answered within 2 minutes. He really is a SUPER HOST.
Top guest favorite
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
4.98 out of 5 average rating, 185 reviews

Bearskin Neck Rockport ★ Amazing Views ★ Parking

ShariRating, 5 stars1 week ago
Just spent 4 days at Christina’s place and had a great time! The location can’t be beat! Beautiful view and right in the middle of all the shops and restaurants. We walked to everything which was great since parking is very difficult to find. Great little coffee house/cafe right across the street was so handy for breakfast. Walked a couple minutes up the road to the infamous Roy Moore Lobster hut for fabulous lobster rolls! Everything you would need is provided at the apartment. Christina even left a little welcome basket with water bottles, snacks and a wonderful candle from her shop downstairs. Would definitely stay here again!
Top guest favorite
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.
Condo in Lakeside Marblehead
4.99 out of 5 average rating, 178 reviews

Harbor Hideaway

JennyRating, 5 stars1 day ago
This is a great place to stay, in a prime location in Marblehead. Easy walk to everything and very comfortable! We appreciated the great snack selection too! Highly recommend. Thanks!
Superhost
A private roof deck is showcased with white lounge chairs positioned on a wooden surface. The backdrop features expansive views of the Boston skyline, highlighting various city buildings against a clear blue sky.
Condo in Back Bay
4.9 out of 5 average rating, 144 reviews

Stunning South End 1BR - private roof deck

SarahRating, 5 stars1 week ago
Stayed for 4 days, 3 nights. Great apartment with fantastic rooftop overlooking city. More personal than just a hotel. Place was just as described, laundry a plus! Host very responsive and friendly. Just stairs are very steep going up and down (3 long flights). So definitely consider this! Would stay again
Superhost
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
4.92 out of 5 average rating, 178 reviews

New Super Modern 2 bed in Waltham

ArnoldRating, 5 stars2 weeks ago
It was the perfect place for our needs, particularly the amenities and location. We have family in the area and would stay there again if the need arises.

Quick stats about vacation rentals with outdoor seating in Winthrop

  • Total rentals

    30 properties

  • Nightly prices starting at

    $70 before taxes and fees

  • Total number of reviews

    5K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

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