
Holiday rentals with outdoor seating in Winthrop
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Winthrop
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winthrop outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Cozy Stylish 4br3ba 3mins to Somerville Subway
We really enjoyed this place. It gave us plenty of room to spread out. The absolute best part was also the location to the green line. So easy to get to and therefore we could easily get everywhere in the city. Would stay here again and recommend to others.

The Gatehouse, Cheerful 3 bedroom 3 bathroom house
We loved the house; very clean and modern. Great communication from the hosts and short distance to great local restaurants and family fun!

Lovely residential home with free parking
Oddays place was wonderful. They have plenty of amenities for guests. It’s an older house, but a very nice older New England home. We enjoyed the stay. The only recommendation we would give is for there to be a laminated card with the wifi name and password, as we didn’t locate it until the last evening of 3 nights there. It was on the Airbnb app but not very clear about how to get the password. That’s our only suggestion as there were older folks in the home as guests and they didn’t have access to the app. Thank you for hosting your Airbnb to us! We would stay again in any future trips to that area.

Rio Stays
Clean, spacious common area, privacy.

Residential home ▪ Billerica ▪ quiet, clean & cozy
This was by far one of the best AirBnb's that we have ever stayed in! The house was perfectly clean and we found absolutely everything we could think of. A well equipped kitchen with really all equipment to cook a good meal and also the rest of the house leaves no wishes open. Barry and Kellie were both extremely friendly and even got us some milk for breakfast (once again thank you). Response time to any question was extremely short. I can only recommend this nice little house to everyone. If we ever return to this area we will surely stay there again. Thank you Barry and Kellie... you made a difficult trip such a lot easier!

The Nest | A peaceful retreat in the city
Pema and Jonathan are wonderful hosts. This was our second stay at The Nest and we were able to really take advantage of the deck overlooking their beautiful garden and the city beyond, for morning coffee and afternoon snacks. Their place is very spacious and charming. It's walking distance to stores, restaurants and the Gilman Square T-stop. For trips further afield, it's great to have a designated, off-street parking spot right by the entrance to the unit, with motion sensor lights for nighttime arrivals. The kitchen is fully equipped and the bed is very comfortable, with reading lights on both sides of the bed. Highly recommend.

Cozy & Modern Entire Residential Home ❤️
Carmen was a wonderful host! The location is perfect to walk everywhere to get a bite to eat or get needed items. Ferry not far away if you want to take it back and forth to Boston. The place was very clean, beds were extremely comfortable, and we had everything we needed.

Fully-Equipped, Private 1st Floor 1-Bed/1-Bath Apt
Our trip to Boston was phenomenal. The Airbnb wasn’t hard to find from the subway station. The neighborhood was beautiful and felt very safe walking thru it. The Airbnb wasn’t hard to find, it felt very welcoming, it felt like I was staying a loved ones home, everything was very well thought out. The bed was very cozy and comfortable for sure something I looked forward to after a long day of sightseeing.
Apartment rentals with outdoor seating

Your Cozy 1 BR Apt & Relaxing Retreat
We had a fantastic stay at this place! The house was spotless, with a fully stocked kitchen and bathroom that made everything super convenient. Thiago was incredibly helpful, attentive, and kind throughout our stay, which made the experience even better. We especially loved the jacuzzi area and the large, comfy couch in the living room. The entire place offered great privacy. Would definitely recommend it!

2 BDR/2b- walk to Seaport & BCEC
Beautiful place! Would definitely stay here again. Hosts communicated very well and replied back with any question I had within the hour. He recommended spot hero for parking that was so easy and worked out really well. We used uber to get into the city, was around 10-minute trip. Not bad at all! Will stay here again when coming to Boston!

🎖The Ashmont Suite | Close to Subway + Downtown🎖
Our stay at Eddie’s home was nothing short of fantastic. An amazing home with beautiful furnishings and rooms, in a brilliant location just a short subway ride away from Boston city centre/downtown Boston. If I can take my family here again I am a lucky man!

5 minutes to downtown. Charming. Clean. Cozy.
Lucia was wonderful to work with. She was quick to give us tips for our trip - having never been to the Boston area. We were very intimidated about the public transportation but Lucia put our mind at ease. Her place felt very safe - even walking from the bus stop at 11pm after a baseball game. Only a few minutes from the bus stop that takes you right into Boston. We used the buses or subway to get all over Boston and it was very easy to navigate from Lucia’s place. The place was clean and quaint. It provided a nice place to relax at the end of a busy day.

Ipswich Apartment
Molly's home was the perfect pick. From the second we walked in, we knew we made the right choice. Before even arriving, Molly reached out & made us feel welcome. Her place truly felt like a home away from home. It was comfortable and cozy. Worried that you forgot something? I guarantee she has an extra there waiting for you. Truly the little things that made a huge difference.

Newly renovated apartment close to downtown.
Nice, cozy spot located close to downtown Salem. There's a really nice outdoor patio that I wish we were able to use more during our stay.

Short Train 2 Boston, Luxury prvt unit w parking
Chris made us feel right at home. The place looks brand new. I’m pretty sure I was the first to use the coffee maker. All the amenities were great and made it easy to cook and clean. Parking place was great and bed was great. Pull out sofa was comfortable for sleeping too. There are so many restaurants (especially Asian) within a 10 minute walk and the Wollaston T stop is 5 minutes away making a 25 minute ride into Boston painless. Our stay was a pleasure! Thanks Chris.

Downtown Rockport|King Bed w/Parking|Walk to Train
Rachel was a great host! Very responsive and gave great instructions to check in and check out. The apartment itself was clean, cozy, and peaceful as well. It was also very close to everything in town! A great place to stay if you’re visiting Rockport!
Condo rentals with outdoor seating

A Cozy 3 Bedroom Home Close To Boston & Parking
Shirley's place is as described. It is comfortable and generous in size. There is parking available both in the driveway and on the street(with a supplied parking pass) for two cars altogether. Fresh linens are plentiful and the kitchen is very practical for cooking and eating in. Outdoor furniture on the back porch allowed us to invite over friends and socialize in nice weather. It is simple, but comfortable.

Family Home + Near Downtown + Cool Backyard!
We had a great stay! Quiet, safe neighborhood, easy to get to the city. Lots of space for the six of us to eat and relax together. Beautiful view of the Boston skyline just minutes walk from the place. Comfortable beds and soft sheets too! We also had no troubles parking nearby and leaving our car (for free) for our entire stay.

My Place - 2 Bedroom Condo with Parking
Located in a lovely neighborhood, this place is a gem! So well appointed, there was nothing we could have needed that wasn’t there! The decor was beautiful and Kelly provided so many extra touches. The kitchen was well equipped, including spices, Keurig Cup Pods, tons of dishes, and utensils. The bedrooms were lovely and very comfortable beds. We can’t wait to come back!!!

Spacious Dorchester Retreat | 2-bdrm condo
We very much liked staying there. It is a nice neighborhood and very close to South Bay shopping mall with many restaurants and easy and convenient shopping. It is also very close to all major attractions in Boston but much quieter environment. Our host, Marian was extremely helpful, proactive and super responsive, the best we have had so far in our trips. I strongly recommend this place to families.

Cozy Entire Unit Condo close to UMASS Lowell
This home was absolutely perfect for our stay! It was clean, spacious, and beautifully decorated. The open layout made it feel very comfortable, and everything was spotless upon arrival. We especially appreciated how well-stocked and organized everything was—from the kitchen to the bathrooms. The host was responsive and welcoming. We’d definitely love to stay here again!

Harbor View Suite
This was the second time we had stayed at Kristin’s. We loved it so much last year we had to come back! Nothing beats the view from the rooftop deck. Everything you need, to include ample public water access, is just a short walk. We plan on making this a yearly stay. The fact you can bring your pup is an added bonus!

Spacious, cozy home near Boston!
What a gem!! Ana's appartement is amazing. The bedrooms are large with good mattresses and furniture. Kitchen is great too. There is a nice patio to sit on at the back. Ana's house is extrememy clean, cosy and very well maintained, we will definitely stay here again when we visit Boston!

Samuel Tucker House - Downtown Luxury 2 Bed Condo
Lovely trip back to Marblehead for my granddaughter’s graduation. This home was comfortable and great care taken to provide more than the basics making it welcoming and like home!
Quick stats about holiday rentals with outdoor seating in Winthrop
Total rentals
30 properties
Nightly prices starting at
$117 NZD 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
Wi-Fi availability
30 properties include access to Wi-Fi
Destinations to explore
- Boston Holiday rentals
- The Hamptons Holiday rentals
- Hudson Valley Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Jersey Shore Holiday rentals
- Pocono Mountains Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Rentals with beach access Winthrop
- Rentals with a washing machine and dryer Winthrop
- Fitness-friendly rentals Winthrop
- Family-friendly rentals Winthrop
- Beachfront rentals Winthrop
- Rentals with a fireplace Winthrop
- House rentals Winthrop
- Pet-friendly rentals Winthrop
- Waterfront rentals Winthrop
- Apartment rentals Winthrop
- Rentals with a patio Winthrop
- Rentals with outdoor seating Suffolk County
- Rentals with outdoor seating Massachusetts
- Rentals with outdoor seating United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Hampton Beach
- Boston Common
- Fenway Park
- Revere Beach
- TD Garden
- Harvard University
- Lynn Beach
- Brown University
- Duxbury Beach
- North Hampton Beach
- New England Aquarium
- Sagamore Beach
- Faneuil Hall Marketplace
- Freedom Trail
- Canobie Lake Park
- Crane Beach
- Sandwich Glass Museum
- Good Harbor Beach
- Prudential Center
- Roger Williams Park Zoo
- MIT Museum
- Rye North Beach
- Museum of Fine Arts, Boston
- Quincy Market