
Holiday rentals with outdoor seating in Winthrop
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Top-rated rentals with outdoor seating in Winthrop
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.
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Popular amenities for outdoor seating rentals in Winthrop
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 ❤️
We loved the apartment, it was very clean and beautifully decorated. As a family of four we fit comfortably. It’s in a perfect location for getting around Massachusetts. The town was very cute with lots of delicious restaurants and so close to the beach. After a whole day of sightseeing and walking it was nice to come back to the home relax and watch tv in front of the fireplace. Thank you Carmen for the lovely stay.

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

Modern Salem: Whole 2 Bed 2 Bath Unit
Graham's place was very enjoyable to stay at! We were very comfortable and everything was very nice.

Winter Island Retreat
Our stay at Dave's place on Winter Island was spectacular! The photos do not do justice for the views. The yard is beautiful and well-kept, and my favorite part was sitting on the porch with my coffee each morning. Inside is cozy, but perfect for two guests. Dave has all you'll need in the kitchen and bathroom, which was a bonus! We traveled from New Mexcio, and it was a long ways, but I would absolutely stay at Dave's place again if we come back to the area. You won't find a better accommodation, and at this price, just amazing. So grateful I was able to bring my daughter for such an incredible stay in Salem.

Your Cozy 1 BR Apt & Relaxing Retreat
Beautiful accommodations. Very comfy. Love the hot tub. Woburn ( pronounced WooBun lol ) is such a cute little hamlet. Good restaurants in walking distance. Strongly recommend Arancini’s. “Wicked” close to Boston. If needing to come back to the area I will seek out this again !!

Light-Filled Luxury Apartment with View
Wonderful one of a kind studio in a very old beautiful house. Plenty of room, lots of light, modern appliances. I enjoyed every minute of it.

Amazing Ocean View In-Law Apt.
Beautiful views and very spacious, everything was perfect. Susan was a great host. We will definitely be back. Thank you!

🎖The Ashmont Suite | Close to Subway + Downtown🎖
Impeccably clean! Wonderful linens and towels. Roomie space inside, perfect for several people. Modern bathrooms and kitchen.

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.
Apartment rentals with outdoor seating

A Cozy 3 Bedroom Home Close To Boston & Parking
This place was absolutely lovely. All weekend my guests and I would find ourselves commenting on how clean, cozy, and cute the space was, and how responsive Shirley was in helping us navigate check in/out. Would absolutely stay here again!

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee
Everything about the stay was excellent! Very welcoming, clean and comfortable. Everything was as described and really appreciated the attention to comfort and hospitality including the snack basket, chocolate, various coffees, and waters in the fridge. Great, quiet location within walking distance to grocery stores, coffee shops, Mass Ave., and across the river from BU. Hoping it's available the next time I visit.

My Place - 2 Bedroom Condo with Parking
The house is very modern and comfortable and has everything you require . It’s a good and safe neighbourhood as well and we had a comfortable stay here. Thank you for hosting !

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
Our stay at Kristen’s on our East Coast tour was incredible. The location and the views were incredible! Her home was pristine and we loved all of the personal touches. Would love to visit again!

Spacious, cozy home near Boston!
This was a fabulous stay and Ana is incredibly wonderful and communicative! We had a great time and the place was better than expected☺️

Boston Rooftop Retreat
Chandra is an amazing host; she was very responsive and helpful when we were looking for something to do on our rainy last day. She also supplied umbrellas, which we could not have done without! The place is even cuter in person; it's updated and has a cozy vibe and a nice record player with a good album selection and lots of cool art made by Chandra! My favorite is the Mr. T sculpture! The keypads on the inside and outside building doors are very convenient and simpler to use than having to carry a key. Nice newer shower and comfortable bed. Large kitchen, comfy couch, and just a cute, interestingly decorated apartment. The rooftop patio is so nice...it's got a grill and 360 views. I wish the weather had been nicer so we could have hung out there more. Not really close to many bars or restaurants, but an easy walk to the train station or the bike rentals and a 30-minute (ish) walk to the Fenway Park area. I would stay there again; it felt like home.
Quick stats about holiday rentals with outdoor seating in Winthrop
Total rentals
30 properties
Nightly prices starting at
$90 SGD 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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- 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