Holiday rentals with outdoor seating in Winthrop

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

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Popular amenities for Winthrop outdoor seating rentals

Holiday House Rentals with Outdoor Seating

Superhost
Home in Somerville
4.89 out of 5 average rating, 127 reviews

Cozy Stylish 4br3ba 3mins to Somerville Subway

DanaRating, 5 stars2 weeks ago
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.
Top Guest favourite
Home in Dedham
5 out of 5 average rating, 214 reviews

The Gatehouse, Cheerful 3 bedroom 3 bathroom house

CrystalRating, 5 stars3 weeks ago
We loved the house; very clean and modern. Great communication from the hosts and short distance to great local restaurants and family fun!
Superhost
Home in Malden
4.8 out of 5 average rating, 112 reviews

Lovely residential home with free parking

NicholasRating, 5 stars1 week ago
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.
Guest favourite
Home in Revere
4.85 out of 5 average rating, 251 reviews

Rio Stays

VinsanRating, 5 stars4 days ago
Clean, spacious common area, privacy.
Top Guest favourite
Home in Billerica
4.98 out of 5 average rating, 219 reviews

Residential home ▪ Billerica ▪ quiet, clean & cozy

GabyRating, 5 stars2 weeks ago
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!
Top Guest favourite
Home in Somerville
4.98 out of 5 average rating, 142 reviews

The Nest | A peaceful retreat in the city

SteveRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Winthrop
4.87 out of 5 average rating, 69 reviews

Cozy & Modern Entire Residential Home ❤️

Kasey Kiley SlotterRating, 5 stars6 days ago
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.
Guest favourite
Home in Jamaica Central - South Sumner
4.94 out of 5 average rating, 165 reviews

Fully-Equipped, Private 1st Floor 1-Bed/1-Bath Apt

ArleenRating, 5 stars2 weeks ago
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

Guest favourite
Apartment in Woburn
4.94 out of 5 average rating, 152 reviews

Your Cozy 1 BR Apt & Relaxing Retreat

VivianaRating, 5 stars2 weeks ago
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!
Guest favourite
Apartment in South Boston
4.93 out of 5 average rating, 127 reviews

2 BDR/2b- walk to Seaport & BCEC

KellyRating, 5 stars1 week ago
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!
Guest favourite
Apartment in Dorchester
4.94 out of 5 average rating, 105 reviews

🎖The Ashmont Suite | Close to Subway + Downtown🎖

JohnRating, 5 stars1 week ago
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!
Guest favourite
Apartment in Chelsea
4.94 out of 5 average rating, 386 reviews

5 minutes to downtown. Charming. Clean. Cozy.

DesiraeRating, 5 stars1 week ago
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.
Guest favourite
Apartment in Ipswich
4.87 out of 5 average rating, 295 reviews

Ipswich Apartment

FelixRating, 5 stars1 week ago
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.
Guest favourite
Apartment in Salem
4.91 out of 5 average rating, 103 reviews

Newly renovated apartment close to downtown.

PatrickRating, 5 stars1 week ago
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.
Guest favourite
Apartment in Quincy
4.96 out of 5 average rating, 182 reviews

Short Train 2 Boston, Luxury prvt unit w parking

JimRating, 5 stars1 month ago
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.
Guest favourite
Apartment in Rockport
4.95 out of 5 average rating, 110 reviews

Downtown Rockport|King Bed w/Parking|Walk to Train

SahilRating, 5 stars5 days ago
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

Guest favourite
Condo in Somerville
4.85 out of 5 average rating, 223 reviews

A Cozy 3 Bedroom Home Close To Boston & Parking

GaleRating, 5 stars1 week ago
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.
Guest favourite
Condo in East Boston
4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

RogerRating, 5 stars3 months ago
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.
Top Guest favourite
Condo in Salem
4.96 out of 5 average rating, 258 reviews

My Place - 2 Bedroom Condo with Parking

Birdie NewmanRating, 5 stars1 week ago
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!!!
Guest favourite
Condo in Roxbury
4.97 out of 5 average rating, 110 reviews

Spacious Dorchester Retreat | 2-bdrm condo

EsfandiarRating, 5 stars5 days ago
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.
Guest favourite
Condo in Dracut
4.85 out of 5 average rating, 117 reviews

Cozy Entire Unit Condo close to UMASS Lowell

LucyRating, 5 stars4 weeks ago
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!
Top Guest favourite
Condo in Lakeside Marblehead
4.99 out of 5 average rating, 225 reviews

Harbor View Suite

KaitlinRating, 5 stars2 weeks ago
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!
Superhost
Condo in Somerville
4.83 out of 5 average rating, 198 reviews

Spacious, cozy home near Boston!

StephaneRating, 5 stars1 week ago
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!
Top Guest favourite
Condo in Lakeside Marblehead
4.98 out of 5 average rating, 111 reviews

Samuel Tucker House - Downtown Luxury 2 Bed Condo

CarolRating, 5 stars1 week ago
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

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