The Chester: Urban Chic Stay In South End
Discover The Chester, A Boutique Stay in the heart of the South End. Relax in a luxurious king-size four-poster bed or accommodate guests on the queen lay flat sofa. Enjoy the living area with a Smart TV and kitchenette equipped for convenience. Expertly designed with restored historic details, painted wood floors, and beautiful rugs, this retreat exudes sophistication. Tucked away off the street, enjoy tranquility while being close to all Boston has to offer.
Rooms and Beds
Dining room
Kitchen
Living room
Living room
Full bathroom
Features and Amenities
Rates and Availability
Taxes and fees are additional
Reviews
Lovely studio with a bonus sitting/sleeping room (with closable door) that made it a perfect place for a family or
Lovely studio with a bonus sitting/sleeping room (with closable door) that made it a perfect place for a family or a group of one to three people. Very nice location. Lots of design touches that made the place feel unique. Well stocked for prepping basic foods, even though the neighborhood has lots of good eating options. A couple of blocks from the T and easy to get to/from in public transport. Drew was very responsive to questions and we were perfectly happy with our choice. Super comfy bed and effective climate control. Bathroom had great water pressure and everything was clean. If you have a desire to stay in south end, this is a good option.
Drew’s place is stunning
Drew’s place is stunning. The architectural details are beautiful and the apartment was immaculately clean.
The location is close to public transport and we were able to walk to many of our destinations such as the Gardner Museum and Fenway. Drew quickly responded to my questions. We had a lovely time.
Thank you!
The space was exactly as described
The space was exactly as described. All the vintage accents were really cool. We felt comfortable there right away. I asked a question and the host got back to me right away. I have nothing but positive things to say and if you are going to Boston you should stay here.
Apartment was beautiful
Apartment was beautiful! We enjoyed our stay and I would love to come back the next time I visit Boston!
When
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Lovely studio with a bonus sitting/sleeping room (with closable door) that made it a perfect place for a family or
Lovely studio with a bonus sitting/sleeping room (with closable door) that made it a perfect place for a family or a group of one to three people. Very nice location. Lots of design touches that made the place feel unique. Well stocked for prepping basic foods, even though the neighborhood has lots of good eating options. A couple of blocks from the T and easy to get to/from in public transport. Drew was very responsive to questions and we were perfectly happy with our choice. Super comfy bed and effective climate control. Bathroom had great water pressure and everything was clean. If you have a desire to stay in south end, this is a good option.
Drew’s place is stunning
Drew’s place is stunning. The architectural details are beautiful and the apartment was immaculately clean.
The location is close to public transport and we were able to walk to many of our destinations such as the Gardner Museum and Fenway. Drew quickly responded to my questions. We had a lovely time.
Thank you!
The space was exactly as described
The space was exactly as described. All the vintage accents were really cool. We felt comfortable there right away. I asked a question and the host got back to me right away. I have nothing but positive things to say and if you are going to Boston you should stay here.
Apartment was beautiful
Apartment was beautiful! We enjoyed our stay and I would love to come back the next time I visit Boston!
The Chester is such a neat spot
The Chester is such a neat spot!! Very much appreciated the cool architecture and the superb amenities. The bed is amazingly comfy, the shower head and water pressure were much appreciated and just a very comfortable stay overall. The location is great because it’s walkable to pretty much everywhere in Boston (we walked over 5 mi everyday easily). If that’s not your thing, public transit is very close and easy to navigate. South End has some delicious restaurants and bars, and so there’s no shortage of sightseeing, eating/drinking, shops and exercise!! Would stay here again!!
The place very nice, spacious no complaints
The place very nice, spacious no complaints
Great place to stay for a weekend visit
Great place to stay for a weekend visit.
Great experience and historic feel
Positive:
Beautiful classy property exceeded expectations
Negative:
No elevator
The appartement was very clean and beautifully decorated, and I immediately felt at home
The appartement was very clean and beautifully decorated, and I immediately felt at home. Everything was thoughtfully provided, from shampoo to dishwashing detergent, which made the stay even more comfortable. The location is very easy to reach, with public transportation close by. Drew was also very friendly and always responded quickly to messages. I would definitely recommend this place.
I love the place
I love the place. Everything is clean. A lot of nice restaurant near by. The host is very nice, and response to my question fast. Highly recommonded
Great location, wonderful studio
Great location, wonderful studio.
Pretty chill, 7/10
Pretty chill, 7/10
Amazing place in a very convenient location, in close proximity to many great restaurants
Amazing place in a very convenient location, in close proximity to many great restaurants. It looks exactly like it does in the pictures. The Airbnb had everything we needed. Highly recommend it! We will definitely stay again!
Great location and stay
Great location and stay! Everything was just as shown in the pictures!
Wonderful place to stay with older, but nicely renovated, New England charm
Wonderful place to stay with older, but nicely renovated, New England charm. The location was great and Drew was very helpful setting things up. We had a great time!
Perfect location and very comfortable flat with very nice fittings
Perfect location and very comfortable flat with very nice fittings. Will stay again if in town.
Thanks Drew
Great, cosy stay in Boston – thank you Drew!
Great, cosy stay in Boston - thank you Drew!
A hidden gem in Boston! This place is in a…
A hidden gem in Boston!
This place is in a beautiful, quiet neighborhood and located in a historic building full of charm. The interior is not only tasteful and stylish, but also incredibly high quality — especially the bed, which was super comfortable. Communication was smooth and responsive, making the whole stay a first-class experience. Highly recommended!
We loved staying at Drew’s place for the weekend. It…
We loved staying at Drew's place for the weekend. It was in a great location- walkable, peaceful! I recommend staying here!
Drew’s place was as advertised in the pictures and definitely…
Drew’s place was as advertised in the pictures and definitely can recommend this place to others.
We had a wonderful stay at Drew’s place in Boston….
We had a wonderful stay at Drew’s place in Boston. The location is absolutely perfect—close to everything, making it easy to explore the city. The apartment itself is beautifully decorated, thoughtfully organized, and incredibly comfortable. It had everything we needed, and the attention to detail really made a difference. It felt warm and inviting, like a true home away from home.
One thing to note is that the house was quite cold, and the heating schedule wasn’t ideal. I often had to wear a jacket or sweatshirt indoors. Also, the street in front can be quite noisy, so light sleepers might want to keep that in mind.
That said, we truly loved our stay and appreciated how welcoming and well-maintained everything was. The space has a great atmosphere, and we would absolutely recommend it to others. Thanks again for a lovely experience!
We booked this place for my in laws to stay…
We booked this place for my in laws to stay in when they visited us in Boston for a month. They really enjoined their stay and found that the home had everything you might need for a long term stay. The host was very responsive!
Great place – super clean, comfortable bed, well stocked, close…
Great place - super clean, comfortable bed, well stocked, close to transit. Only downside is that because this unit faces on to the street, the traffic is quite noisy into the night.
We loved our stay! The place was perfect for two…
We loved our stay! The place was perfect for two people. Very clean and we appreciated the interior design. Drew was very responsive and helpful. Make sure to check out the restaurant on the corner (Mida); it was so fun to walk out of the AirBnb to a great restaurant!
We had a wonderful stay. There are some really good…
We had a wonderful stay. There are some really good restaurants near by and train/bus stops where a close enough of a walk so we can get around the city.
This location was exactly as described. Drew was very responsive…
This location was exactly as described. Drew was very responsive to every message that I sent (usually within 15 mins). I had a friend who was showing us around, and I reached out to Drew to notify him that my friend may stay a night. Drew immediately altered my stay from 2 people to three. He was very accommodating. He told me what apps to get to find a parking spot--which was very helpful. Overall, I would definitely stay at this location again! Thanks a lot, Drew!
The place was super clean and charming, a perfect space…
The place was super clean and charming, a perfect space for me to unwind after busy days.
Appartamento molto bello. Consiglierei di attrezzare la cucina meglio.
Appartamento molto bello.
Consiglierei di attrezzare la cucina meglio.
Immaculate brand new & gorgeously acquainted studio in the South…
Immaculate brand new & gorgeously acquainted studio in the South End! Walking distance to so many restaurants and green spaces. Bed & linens very comfortable. Such a cool location but def noisy overnight since it’s a thorough way- bring white noise machine and that helps. The location & beautiful studio trumped the noisy night IMO. Thanks again Drew- we hope to come back and stay again- Boston has so much to offer!!
We had a fantastic stay at Drew’s. Space was very…
We had a fantastic stay at Drew’s. Space was very clean and cozy. Great location. Mt friends and I come to Boston frequently and my friend said this has been her favorite place we’ve ever stayed
Perfect
Positive:
Really nice location, close to the fine art museum.
Wonderful room with a beautiful view. We really enjoyed our stay here, wish can come back again
Difficult to sleep with all the sirens and cars honking,…
Difficult to sleep with all the sirens and cars honking, on the main drag. Figured out how to close the windows all the way on second night - one person to push upper section up, another pushes bottom section down.
Brand new place, squeaky clean except for one throw pillow.
Missing a blanket, host rectified it the next day.
Entire building is AirBnB - upstairs neighbors did a lot of clonking around on the wood floors.
Host was very nice, communicative, accommodating. Kitchen, bathroom were awesome. No stove or dishwasher. Apparently no where to take the trash during our stay - left bags in the kitchen. Not ideal if it were an extended stay
房子在一栋老建筑中很漂亮，楼下有不错的餐厅，离地铁500米。一切都很好，唯一的问题是，新装修的味道还有，过一个月应该就会很好。 汽车声音对需要安静的人来说可能会影响，我们睡的挺好。
房子在一栋老建筑中很漂亮，楼下有不错的餐厅，离地铁500米。一切都很好，唯一的问题是，新装修的味道还有，过一个月应该就会很好。
汽车声音对需要安静的人来说可能会影响，我们睡的挺好。
Very responsive and friendly. The place was absolutely beautiful and…
Very responsive and friendly. The place was absolutely beautiful and very very clean. It’s a little noisy outside since it’s in a vibrant neighborhood but other than that, everything was perfect and according to the description