
Holiday rentals with outdoor seating in Chelsea
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Top-rated Holiday Houses with Outdoor Seating in Chelsea
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Popular amenities for Chelsea outdoor seating rentals
Holiday House Rentals with Outdoor Seating

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.

Stone Cottage with meadow view
Lauren was an excellent host! Cottage is absolutely beautiful! Felt right at home , she was very responsive and very helpful. This place has all the amenities, perfectly located for everything we had planned .

Spacious New 3 bed 2 Bath home 15 min from Airport
We had a great stay! The house was very clean and in a quiet neighborhood. It was easy to find and made a perfect central spot for visiting Boston and exploring the coast. Javer was super responsive and communicated clearly throughout—would definitely stay again!

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.

2BR—Lovely 1900s Home—1200sqft—25 Min to Boston
Andrea’s place was amazing! We stayed for a week and it was so clean and wonderfully organized. All instructions were clear, and Andrea was very kind and responsive!

Sunny home minutes from Boston. Free parking.
We really enjoyed our stay. Such a Warm and cozy home. Elizabeth was easily reachable whenever we had a question. Would highly recommend her cozy home. Thanks Elizabeth

Upscale 5BR Family Home Near Boston
The home was in a very nice and quiet area of town with groceries, gas and restaurants a short walk or drive away even in during busy hours of Boston traffic. The home was actually larger than expected with two full bathrooms, one on each floor. Everything was clean and ready for us with a well equipped kitchen and filtered water. There was a nice booth area to eat as well as counter seating and a dining room. We only had three in our party, but you could comfortably house a much larger family in the rental. We have a few more trips planned to Boston this year and will book this first if it is available, would like to stay again.
Apartment rentals with outdoor seating

Stunning Union Square 2 bed/2 bath w/ shared patio
Our stay was fantastic. The property was exactly as described—clean, well-maintained, and in a great location. The layout was perfect for our group, making it easy to relax and enjoy our time together. The beds were very comfortable, and having a secure and clearly defined parking area made things even more convenient. Jay was incredibly responsive and thoughtful, which made the entire experience seamless. This is a great spot for anyone looking for a comfortable, hassle-free stay. We’d definitely return and highly recommend it.

Near Boston / Everett historic two-bedroom
Mark's home & hospitality were stellar! We had a last minute reservation that he was able to accommodate several hours later on the very same day. HIs place is just as described. It's full of charm & character, from all the beautifully preserved wood elements throughout to the sparkling tiled bathroom. He actually lives in the unit connected to it & has done an exceptional job renovating both the inside & outside. It feels homey, which is exactly what we look for when we're away from ours. Additionally there were nice added touches like responsibly sourced toiletries & kitchen supplies which all really stood out to us. Being from a warmer climate personally, it was nice knowing there were window a/c units to count on for warmer days/nights throughout the unit also. The coffee provided was the little cherry on top in the mornings when we enjoyed the lovely covered back porch & views of his private garden/patio areas. Don't miss this place if ever in town- it's the Grand Dame of Boston!

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.

Close to Harvard, MIT & Boston, Gym and Patio!
Melanie’s place was exactly as described and very clean. She was very helpful and clear with the instructions to check in and check out. The area was very nice and peaceful and you can access most of Boston very easily.

Warm home in Lexington, walk to town, nature trail
Had a great stay in Xunzhong's place. Good location, easy parking, tidy, well stocked with all the basics, simple check in/check out, quiet and quick and easy communication. Really appreciated that they had a pack n play, high chair and baby gate set up already for our 16 month old. They also accommodated our request for an hour later check out which really helped us out! Overall would stay again.

Spacious, private apartment in perfect location
As mentioned in other reviews, this place was truly amazing! While other accommodations in Boston were quite expensive, this one was much more affordable without compromising on quality. There were many places within walking distance, which made it easy to enjoy shopping and great food. The neighborhood was quiet and peaceful, making it a perfect environment for studying. If I ever come back to Boston, I’d definitely stay here again. Highly recommend it!

Garden apartment in the heart of Kendall Square
Hosts have thought of everything. No need to purchase tea, coffee, condiments nor soaps-all provided. The layout, beautiful and clean rooms, counters, shower and restroom all wonderful. Linens lovely. Bed and pillows comfy. A summer weight blanket would be nice. Garden as pictured. Directions to work the Nest climate control would be helpful but it worked great. Highly recommended.

Sunny, private, comfortable 1 bedroom-convenient.
I felt very much at home in Chris’s place. It was clean and comfortable and a great base for visiting the Newton area
Condo rentals with outdoor seating

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
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.

Samuel Tucker House - Downtown Luxury 2 Bed Condo
Bryan was very communicative. Instructions were easy to follow and thorough. Good location and comfortable

The Salem Porch House
The best place to stay in Salem and the best host I’ve encountered on Airbnb to date. Alex and David were friendly, thoughtful, communicative and accommodating. Their place is spacious, quaint and comfortable. We made great use of the great location across from the common, walking into the city center for all our outings. We couldn’t have had a better time and stay, thank you so much!

Stylish garden level studio with a private patio
We had a great stay at this lovely place in East Boston. Everything was spotless and just as pictured. The hosts were also super gracious to let us check in early and store our luggage while we did some more sightseeing our last day.

Luxury Condo in Boston w/ backyard & parking
Cusaj's place was a wonderful haven to return to after a busy day of sightseeing. The beds were very comfortable. Her place was very clean. Also, some nice restaurants in the area..

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 Chelsea
Total rentals
40 properties
Nightly prices starting at
$83 NZD before taxes and fees
Total number of reviews
5.5K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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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
- Faneuil Hall Marketplace
- Freedom Trail
- Canobie Lake Park
- Crane Beach
- Good Harbor Beach
- Prudential Center
- MIT Museum
- Roger Williams Park Zoo
- Rye North Beach
- Museum of Fine Arts, Boston
- Onset Beach
- Isabella Stewart Gardner Museum
- Quincy Market