The Chester: Modern Luxury, Historic Charm
Discover The Chester, A Boutique Stay in the heart of the South End. Combining modern with classic charm, this one-bedroom suite sleeps up to four guests with a queen bed and queen layflat couch. Enjoy the sleek kitchenette with a mini-fridge, microwave, sink, and induction cooktop. The bathroom features classic tile and a glass-enclosed stand-up shower. Book this unique Boston experience today!
Rooms and Beds
Sofa bed
Primary
Full Bathroom 1
Features and Amenities
Rates and Availability
Taxes and fees are additional
Reviews
The Chester was a delightful property—clean, quiet, and a lovely aesthetic that suited me to a T
The Chester was a delightful property—clean, quiet, and a lovely aesthetic that suited me to a T. Plenty of extra towels were on hand too. The bed was extremely comfy, and the one bedroom flat was quite spacious for a single traveler like myself, but would also suit a couple. Drew’s place feels like a home away from home—unlike a hotel. I’ll definitely book here again.
This was a great Airbnb
This was a great Airbnb! I came with my husband and two small kids (3 and 5) and it was plenty of space. Drew was extremely responsive, answering my texts within minutes. The apartment is as described, no surprises. The bed and the sofa bed are super comfortable. And the location cannot be beat. Walkable to a million restaurants as well as the prudential, which I had to go to for a conference. Would definitely stay here again.
Positive: Beautiful furniture, everything was clean Negative: It doesn’t have elevator
Positive:
Beautiful furniture, everything was clean
Negative:
It doesn’t have elevator
Drew’s place was really nice, clean, comfortable, and had everything we needed
Drew’s place was really nice, clean, comfortable, and had everything we needed. The location was convenient with the public bus and T very close by, which made getting around easy. The area felt a little rough at night, but overall it was a good stay.
When
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The Chester was a delightful property—clean, quiet, and a lovely aesthetic that suited me to a T
The Chester was a delightful property—clean, quiet, and a lovely aesthetic that suited me to a T. Plenty of extra towels were on hand too. The bed was extremely comfy, and the one bedroom flat was quite spacious for a single traveler like myself, but would also suit a couple. Drew’s place feels like a home away from home—unlike a hotel. I’ll definitely book here again.
This was a great Airbnb
This was a great Airbnb! I came with my husband and two small kids (3 and 5) and it was plenty of space. Drew was extremely responsive, answering my texts within minutes. The apartment is as described, no surprises. The bed and the sofa bed are super comfortable. And the location cannot be beat. Walkable to a million restaurants as well as the prudential, which I had to go to for a conference. Would definitely stay here again.
Positive: Beautiful furniture, everything was clean Negative: It doesn’t have elevator
Positive:
Beautiful furniture, everything was clean
Negative:
It doesn’t have elevator
Drew’s place was really nice, clean, comfortable, and had everything we needed
Drew’s place was really nice, clean, comfortable, and had everything we needed. The location was convenient with the public bus and T very close by, which made getting around easy. The area felt a little rough at night, but overall it was a good stay.
Great experience
Great experience! Beautiful/clean apartment, good area, very responsive host. Couldn’t have asked for a better experience. Thank you!
The apartment met the expectations, as it is as described and presented in the photographs
The apartment met the expectations, as it is as described and presented in the photographs.
It doesn't have a closet or chest of drawers, so expect to live out of a suitcase, however, the apartment has the small, but separate bedroom, which is nice
Negative: Falta ascensor
Negative:
Falta ascensor
Place was comfortable and just as described
Place was comfortable and just as described. Area is walkable and not far from the T
The apartment is beautifully designed
The apartment is beautifully designed, a true feast for the eyes, with thoughtful touches and a style that welcomes you in and makes you feel both comfortable and pleasantly indulged. The location is very convenient. Drew was a fantastic host – always quick to reply and attentive to any requests.
Just two small side notes: there’s no wardrobe or storage space for clothes, which meant that with four people staying, the gorgeous apartment quickly took on a bit of a “lived-in” look. 😉
And under the bedroom window there are some big air-conditioning units, which made it tricky to keep the window open at night – even in lovely mild weather.
Nevertheless, we had a wonderful time and would absolutely recommend Drew’s place!
Great location. Very responsive hosts.
Great location. Very responsive hosts.
Cozy apartment within easy walking distance to Boston’s top attractions….
Cozy apartment within easy walking distance to Boston’s top attractions. The restaurant downstairs is top notch too!
Modern, clean, very well located apartment.
Modern, clean, very well located apartment.
The apartment was very comfortable. We are a family of…
The apartment was very comfortable. We are a family of four and felt we could spread out easily. The location is very walkable. There are a few restaurants in the area. We tried the one across the street and loved it. They had fresh juices, salads, and sandwiches. If you are like us and like to feel like a local when you travel, this is the accommodation for you.
Great stay and nice place
Great stay and nice place
There’s lot of positives about Drew’s place – the location,…
There’s lot of positives about Drew’s place - the location, the space is clean and cute, the beds very firm and comfortable. The drawbacks - I was staying there during a particularly cold couple weeks and the apartment was cold (never over 69/70). There was a problem with the heat, and Drew sent someone in to do repairs, but it both took a while for that to happen and once the repairs were done it got a little warmer but not much. While Drew was quite responsive - I think some of the responses were from a predictive AI - bc I would sometimes get the same canned response to my inquiries about the heat multiple times. All and all I think it’s a good spot for a weekend stay, but I’d say proceed with caution for a longer term stay.
We loved this place! It was a great spot for…
We loved this place! It was a great spot for a mother-daughter trip. It was just the right size and had everything we needed. We haven't stayed in this area before and really liked the architecture, the laid back feel, and the proximity to all the sights in Boston we wanted to take in. This spot was a great blend of lively (but not overwhelming) and peaceful (but not boring). We loved walking for coffee and admiring the brownstones. The best meal of our trip was at Mida, and the proximity was a lucky bonus. Drew was very helpful with suggestions for bag storage when our flight was changed to arrive much earlier than the listed check-in time. He also provided the option of starting our reservation early since the unit was available, which we were glad to take advantage of. Thanks for a great Boston stay!
Great place to stay for a few days over the…
Great place to stay for a few days over the Thanksgiving break. It was close to coffee shops and restaurants. The apartment was clean and spacious, and the host was easy to communicate with and accommodating. We would be happy to come back on our next Boston trip.
Was such a great stay, perfect location to walk to…
Was such a great stay, perfect location to walk to the prudential center, Fenway or hop on the T. The apartment was spotless and has all the necessities!
True Boston experience! Comfortable and so quaint! Great location-
True Boston experience! Comfortable and so quaint! Great location-
Stylish flat in a great city location.
Positive:
Great location just 2 blocks from train station and walkable to lots of places in SoWa. Neighborhood is a little spicy at night but that’s to be expected in a city. Pretty quiet in the apartment once we got upstairs. Comfy bed and lovely bathroom and a well equipped kitchenette with everything you need for a couple of days. Would stay here again!
Negative:
Looked like someone had tried to break in at some point. Damage to door jam should be addressed.
Beautiful room at a great location. We were able to…
Beautiful room at a great location. We were able to walk to all the places we wanted to visit. The bed and sofa bed were both comfortable. Everything seemed recently renovated and decorated with style!
Great location
Great location
great stay. walking distance or short Uber ride to everything….
great stay. walking distance or short Uber ride to everything. place was clean and really easy to get into, rented parking space near by. drew was a responsive host and good communicator. would stay here again.
Great spacious apartment that has obviously just been renovated -…
Great spacious apartment that has obviously just been renovated - everything is new and clean. It has all the amenities for a comfortable stay and lots of little things to make life easier. Special thanks for the great quality cotton sheets! One small note is the steps (no elevator in the building) - there are between 20 and 40 from the sidewalk to the door depending on the floor you get the apt on. The steps are quite steep and do not look suitable for the very elderly.
Drew was a great host who also provided local support when we needed it.
This is the place to stay if you want to…
This is the place to stay if you want to be in the middle of things! The apartment is nicely-appointed and cozy, located within two blocks of a T station (and then just minutes from all of the places you want to go in Boston), and super clean.
Beautiful apartment in the best location – everything is easy…
Beautiful apartment in the best location - everything is easy to get to and has great walk ability and close to public transportation. Excellent, responsive host who was extremely helpful. 10/10 recommend and will return.