
Vacation rentals with outdoor seating in Winthrop
Find and book unique outdoor seating rentals on Airbnb
Top-rated outdoor seating rentals in Winthrop
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Popular amenities for Winthrop outdoor seating rentals
House rentals with outdoor seating

Adorable renovated house, steps from Front Beach
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.

Downtown Luxury Villa on the Plymouth Waterfront
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.

Tiny house experience steps from the water!
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.

Charming Home in Reading with a Large Yard
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

Backyard Oasis with Hot Tub
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!

"The Fieldstone Beach House"
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.

The Mojito House with Hot Tub, Arcade and Theater.
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!!

Gloucester Beach House, near Good Harbor Beach!
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

Two bedroom Apt with a deck
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.

Entire 1st floor apt in charming seaside Beverly
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!

Couples Retreat - Apt in Charming Colonial Home
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!

Downtown Backyard Oasis
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.

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

“Very Modern Apartment” Dedicated Driveway Parking
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.

2 BDR/2b- walk to Seaport & BCEC
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!

Rare 3.5 bed apt, super location Boston, +parking
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

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

Condo in downtown Boston
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!

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee
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.

KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN
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.

Bearskin Neck Rockport ★ Amazing Views ★ Parking
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!

Harbor Hideaway
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!

Stunning South End 1BR - private roof deck
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

New Super Modern 2 bed in Waltham
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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