The Chester: Penthouse One Bedroom
Discover The Chester, A Boutique Stay in the heart of the South End. Designed to accommodate up to 4 guests, this space features a king bed, a queen pull-out, and a fully equipped kitchen. Enjoy city views, classic Boston Brownstone original crown moldings, smart TVs, and a sleek, modern tiled shower. Expertly decorated with a mix of contemporary and antique furnishings, this urban retreat offers comfort and style at the heart of the vibrant city.
Rooms and Beds
Common Area
Primary bedroom
Full Bathroom 1
Features and Amenities
Rates and Availability
Taxes and fees are additional
Reviews
It was out first time in Boston and we loved it
It was out first time in Boston and we loved it! Staying at the Chester made our stay memorable. Drew was a great host, super responsive and helpful whenever we asked for recommendations or questions. Highly recommend staying here, the place is even better than the pictures.
Stunning apartment Great location Comfortable bed Lovely bathroom Would stay again when visiting our children.
Stunning apartment
Great location
Comfortable bed
Lovely bathroom
Would stay again when visiting our children.
The place was very nice and clean
The place was very nice and clean. The manager communicated well and answered my questions in a timely way, as I was making the reservation for cousins from overseas.
However, I would have appreciated knowing that “penthouse” does not mean top floor. Instead, with check in info just about a day prior to arriving, I received a note that the penthouse was on 1st floor (10 steps up from sidewalk). I had been interested in a top floor apartment since the city can be noisy. I would have much preferred a more accurate description.
Last, the heater in 1/2 the suite wasn’t working and although people came to see whether it is fixable, it still wasn’t working.
I would have appreciated an offer to be even slightly compensated refund for the misleading information about the “penthouse” and the lack of heat in 1/2 the suite.
Otherwise, it was safe and quite pleasant.
Gorgeous space and communicative host
Gorgeous space and communicative host. Great location.
When
Share this property
It was out first time in Boston and we loved it
It was out first time in Boston and we loved it! Staying at the Chester made our stay memorable. Drew was a great host, super responsive and helpful whenever we asked for recommendations or questions. Highly recommend staying here, the place is even better than the pictures.
Stunning apartment Great location Comfortable bed Lovely bathroom Would stay again when visiting our children.
Stunning apartment
Great location
Comfortable bed
Lovely bathroom
Would stay again when visiting our children.
The place was very nice and clean
The place was very nice and clean. The manager communicated well and answered my questions in a timely way, as I was making the reservation for cousins from overseas.
However, I would have appreciated knowing that “penthouse” does not mean top floor. Instead, with check in info just about a day prior to arriving, I received a note that the penthouse was on 1st floor (10 steps up from sidewalk). I had been interested in a top floor apartment since the city can be noisy. I would have much preferred a more accurate description.
Last, the heater in 1/2 the suite wasn’t working and although people came to see whether it is fixable, it still wasn’t working.
I would have appreciated an offer to be even slightly compensated refund for the misleading information about the “penthouse” and the lack of heat in 1/2 the suite.
Otherwise, it was safe and quite pleasant.
Gorgeous space and communicative host
Gorgeous space and communicative host. Great location.
Drew’s place is the perfect New England charm we were looking for
Drew's place is the perfect New England charm we were looking for! The space was beautiful and was perfect for me and my fiance. The house was clean and organized. Drew had great communication and was helpful with our check in process and nearby parking. We definitely enjoyed our stay!
We loved our stay and hope to return to Drew’s place next year
We loved our stay and hope to return to Drew’s place next year. Fantastic, clean, safe location, close to fantastic restaurants he recommended for us. Not to mention just how GORGEOUS this home is! We very much look forward to returning!
This listing completely made our stay in Boston and made us feel like we weren’t just tourists
This listing completely made our stay in Boston and made us feel like we weren’t just tourists, but living in the city. The property is beautiful and in pristine condition. It is very close to a subway station which saved us hundreds of dollars worth of uber rides. The area is beautiful and safe. The only downside would be the loud traffic outside, but that’s to be expected being in the city. I couldn’t recommend this listing more!
An absolutely beautiful apartment and next to some delicious restaurants
An absolutely beautiful apartment and next to some delicious restaurants. If you have the chance to stay here do it!
The area was interesting
The area was interesting ! Drew’s place was beautiful, and the bed was comfy. We made use of the pull out couch and that was comfy too and easy to navigate. The only bathroom is in the main bedroom fyi.
Loved every second of staying here
Loved every second of staying here! Drew was super informative prior to arriving, helpful with instructions on self check in. The place itself was spotless, made us feel right at home, it was exactly like the photos & the bed was so comfy (usually I am veryyyyy picky on vacation beds!). I kept saying “I don’t want to leave!” the night before we had to check out. 10/10, 5 stars all around - I hope to come back soon & stay here again. Thank you, Drew!
The apartment was beautiful and exactly as pictured
The apartment was beautiful and exactly as pictured. Great location, was able to walk everywhere. I had arrived In Boston at 2PM and was hoping to check in a bit early. I understand when this is not possible but when I arrived at the scheduled check-in time of 4:00PM the cleaning crew was still there. The king bed was very comfortable. Please note the listing refers to a “queen pull-out”, many may assume this is a sleeper sofa with a mattress, it is not. Later in the listing it does refer to a “lay-flat sofa” which is more accurate. It is a nice couch but it functions like a futon. Also, was not aware I’d have someone coming over to test the master key which was a bit startling having someone knocking and unlocking the door. I’d also recommend adding some wine glasses, we like to have a glass of wine before dinner and had to drink out of coffee mugs. (There are 6 corkscrews in the drawer). Overall a nice stay with just a couple inconveniences.
Great apartment and location
Great apartment and location. If you are planning to cook, cookware and dishes are quite minimal so could be an issue.
Absolutely love Drew’s place
Absolutely love Drew’s place! This is our second time staying, and we couldn’t have loved it more. Convenient location, squeaky clean, and absolutely beautiful.
This Airbnb is also particularly special because it’s where we stayed when I decided to move to Boston… and then where we stayed when I moved it! Lots of special memories, and it couldn’t have been a more perfect place for them. Couldn’t recommend more and we hope to stay again!
This place is very beautiful- exactly as pictured
This place is very beautiful- exactly as pictured. Drew is very responsive. Thanks so much!
Loved staying here! Amazing location, and the space is just…
Loved staying here! Amazing location, and the space is just beautiful. Will be back again for sure!
This place was beautiful & just like the pictures. Mida…
This place was beautiful & just like the pictures. Mida being next door is a plus.
The apartment was beautiful. It looks just like photos. It’s…
The apartment was beautiful. It looks just like photos. It’s very well furnished. The location is walkable to restaurants and shopping. Drew is very friendly and responded within minutes to address questions. We will definitely stay again.
Drew’s apartment has plenty of period character and is in…
Drew’s apartment has plenty of period character and is in a great location in South End and walkable to Back Bay. It was spacious and clean and suitable for a solo traveller, couple or small family.
Very nice place in a busy area, but the bedroom…
Very nice place in a busy area, but the bedroom is quiet (not near the street) and has a cute office which is also quiet.
Drew’s place is one of the best Airbnbs we’ve stayed…
Drew’s place is one of the best Airbnbs we’ve stayed at. The inside is exquisite—with original historic charm and updated amenities. It also has the most comfortable bed!!
Furthermore, the location couldn’t be better. Everything we wanted to see or do was within a 25 minute walk.
Will for sure stay here again when in Boston.
absolutely stunning place! great location, beautiful interior, caring and attentive…
absolutely stunning place! great location, beautiful interior, caring and attentive owner. this is the most beautiful and stylish place i have ever stayed. will definitely come back again, highly recommend
The apartment is clean and uncluttered and so beautiful!
The apartment is clean and uncluttered and so beautiful!
We enjoyed our stay.
We enjoyed our stay.
We had a wonderful stay at The Chester! The apartment…
We had a wonderful stay at The Chester! The apartment is on the first floor of a historic brownstone with stunning original architectural details. It's beautifully decorated and equipped with everything we needed for our stay. Fantastic location too; we walked all around the Back Bay and South End from the apartment. Drew was a terrific host, always responsive and quite helpful with anything we needed. We want to echo what other reviewers have said about the restaurant Mida, around the corner. It's well worth a visit (or two!). It features New Italian cuisine, delicious and fresh, with artful preparations and inventive flavor profiles. We look forward to a return visit to the neighborhood!
Great stay in beautiful Boston. This place is incredible, a…
Great stay in beautiful Boston. This place is incredible, a designer space in a great neighbourhood walking distance to Fenway, and Beacon Hill and Newberry. Can’t recommend this place enough for a very elevated getaway to Boston!
Our family of 3 had a great stay here. Very…
Our family of 3 had a great stay here. Very safe and walkable with excellent restaurants nearby. The layout of the apartment is one large space that’s divided with giant beautiful sliding French doors into a bedroom towards the back and quieter thankfully!We spot hero’ed a convenient and in/out parking spot for the week about 3 blocks away (just note that streets on Mass Ave closer to boston medical house a homeless shelter nearby). I wouldn’t recommend cooking in the kitchen (just a few pots and pans, and there wasn’t a tea kettle/teas which would have been nice). Bed is a nice king temper-pedic. All in all a very comfortable stay!
We had a great stay! We came in town to…
We had a great stay! We came in town to tour colleges and it was 20 mins from all
The colleges we toured.
The condo was very clean, and comfortable. I loved the the white linens and towels. Teh felt like new.
The host was very helpful and responsive to our questions. The details and architecture inside the condo was beautiful. The restaurants and little market near the condo was really easy to get to and great food. Even though it’s on a busy street and intersection you could not hear any noise from cars, buses, etc. We slept great and would definitely come back!
Thanks again for having us! We had a great stay!
My husband and I had another lovely stay! This is…
My husband and I had another lovely stay! This is our favorite place in Back Bay - South End for so many reasons: comfortable, clean, beautiful, great location. Drew is an awesome host who is very responsive, flexible, helpful and kind. Can’t wait for our next visit!
Amazing! Clean, convenient, and beautiful. Drew was great and we…
Amazing! Clean, convenient, and beautiful. Drew was great and we loved our stay! Our family is accustomed to staying in 5 star hotels, air bnb’s are an unusual occurrence, but we had the best experience. Would come again!
Ps. The restaurant just downstairs (Mida) was exquisite! Incredible food and lovely atmosphere. We ate there 3 times and enjoyed every meal when we didn’t feel like walking more into Boston for food!
We stayed here for a work conference that was being…
We stayed here for a work conference that was being held at a local hotel. So glad we didn't stay at the hotel. A short walking distance to Copley Square afforded us something way more charming and connected to a great city like Boston. Cheap eats like the pizza by the slice shop were close by, along with a juice/coffee bar, or a more formal great Italian place were really close by. The bed and furniture were comfortable. Room sizes were just right for our stay. Decor added to the experience and wasn't a soulless hotel room.
Drew’s place was wonderful and truly appreciate the last minute…
Drew’s place was wonderful and truly appreciate the last minute help to find a place. Everything was great and I would definitely recommend this place to others. Due to a small oversight, our instructions and text message did not include the security code so we called the emergency line and were quickly supported.
Drew’s place was perfect for my family of four, including…
Drew's place was perfect for my family of four, including two ten-year-olds. The location is excellent, and the apartment was just as pictured, and if anything, the fish-eye lens fails to do it justice..
It's a stylish apartment in a great location, and I can recommend it without hesitation.
Best place!
Best place!
What a beautiful stay. 🙂 Drew was easy to communicate…
What a beautiful stay. 🙂
Drew was easy to communicate with and space was exactly as described. Truly stunning!
I recently stayed at the Chester Penthouse during my holidays…
I recently stayed at the Chester Penthouse during my holidays in early January, which was incredible. From the moment I walked in, I was blown away by the attention to detail and tasteful decor. The space was immaculately clean, and spacious, and had all the amenities you could want.
The location was perfect, allowing easy access to Boston's key attractions, restaurants, and public transport. The Restaurants in the area were amazing, I need to mention Mida, Ilona and Toro such enjoyable restaurants, and all within 1-3 mins walk.
Drew was extremely accommodating, every message was answered quickly with perfect details.
I can't recommend The Chester Penthouse enough. If you're visiting Boston and looking for comfort, style, and to stay in a Brownstone, this is the place to be. I'd happily stay here again on my next trip!
Loved this Airbnb! Would recommend to anyone looking to spend…
Loved this Airbnb! Would recommend to anyone looking to spend some time in Boston. It was perfect.
The Chester is now my favorite place to stay in…
The Chester is now my favorite place to stay in Boston! The location is fantastic: close to mass transit, shops, restaurants, NEC, Northeastern, the Pru, Newberry, Fenway. The unit is absolutely gorgeous (looks just like the photos)…we appreciated the high quality, carefully curated art everywhere the eye turns. The bed is extremely comfortable and the bedroom was quiet, especially when we closed the beautiful wooden doors. There was plenty of space for both of us to work remotely and the internet service was more than adequate. I loved the tall ceilings and big windows, while also appreciating the light blocking window shades at night. The self check-in process worked perfectly. Drew was a kind and responsive host, both before and during our stay. Can’t wait to go stay there again!
Fabulous apartment, great location, looks like a page out of…
Fabulous apartment, great location, looks like a page out of Architectural Digest!
Beautiful home with luxurious furnishings. The bed and linens were…
Beautiful home with luxurious furnishings. The bed and linens were first rate. Our favorite experience in Boston!
Much better than any hotel! Lots of space for the…
Much better than any hotel! Lots of space for the two of us. Most everything we did was walkable from our location. Drew was quick to respond to messages. We flew out late the day of check out and were able to find a nearby business that was walkable and able to store our luggage until trip to airport. Would highly recommend!
This place is situated in a great location and has…
This place is situated in a great location and has access to many of the attractions Boston has to .
The bed is comfortable, the apartment is beautiful and although there were some issues during the first week, thankfully it was resolved in a satisfactory way so that the remainder of the trip was quite enjoyable!
Great location and lovely interior design.
Great location and lovely interior design.
Absolutely beautiful space!
Absolutely beautiful space!
Beautiful place in great neighborhood! Everything was super clean and…
Beautiful place in great neighborhood! Everything was super clean and looked just like the pictures. Some tourist spots are only a 15-20min walk away. Would definitely stay here again!☺️
This place is lovely. My wife and I spent our…
This place is lovely. My wife and I spent our honeymoon there. The decor is excellent and the rooms are very spacious. Everything was very clean and neat. The host is quick to respond and check in and out were a breeze. 10/10 would stay there again.
This airbnb was beautiful! Quaint and charming with extremely high…
This airbnb was beautiful! Quaint and charming with extremely high ceilings, gorgeous crown molding, and super clean!
Unfortunately the host provided the incorrect address in the check in message, which made us scrambled and confused when arranging transportation from the airport. Additionally, only one comforter was provided for two beds. I kindly requested another upon our arrival, but it wasn’t provided until our third day. Two nights sleeping uncomfortably without a comforter was a bummer in such a beautiful property. Overall, communication was prompt, but unclear.
Location was stellar. Right next to great restaurants, coffee shops, and transportation options.
This is one of my favorite Airbnbs I’ve ever stayed…
This is one of my favorite Airbnbs I’ve ever stayed in. I want to live here. Amazing location, beautifully designed and decorated, super cozy bed, great products in the bathroom. No notes at all - would absolutely stay here again.
Have no hesitation recommending this place. Property is expansive, beautiful,…
Have no hesitation recommending this place. Property is expansive, beautiful, and very centrally located. Drew was very prompt with his communication.
Thoroughly enjoyed my stay
This place was really really good. I came with my…
This place was really really good.
I came with my wife and my cousin
The way the place was decorated with all of the molding kind of Victorian style really gave us this feel like we are in a town that had lots of history. Had tall ceilings and had the depth of history but in an updated clean way. 
The place was very clean, organized, spacious and set the perfect tone for being in Boston.
The linens like the towels, and the comforters were very soft, clean, and plush pillows.
Great location: espresso and fresh pressed juices across the street, drip coffee down the street 2 blocks, and a great restaurant (Italian) right next door. Best food we had all trip was right next door.
Drew was accommodating and responsive. Great place, great host, great town and great experience. I’d recommend Drew’s place for sure
Mike & Autumn S
Although situated at a busy intersection, the building and accommodations…
Although situated at a busy intersection, the building and accommodations are fabulous, very comfortable, tasteful and well appointed, within walking distance to many restaurants and South End amenities. Like other guests, we found parking in the Stanhope garage just over a block away easy and convenient. Among available options, I opted for The Chester to satisfy my West Coast daughter's idea of a classic Boston walk-up and it did not disappoint. Thank you for a restful, straightforward and lovely stay!
The Airbnb was beautiful. It was well decorated, felt charming,…
The Airbnb was beautiful. It was well decorated, felt charming, extremely clean. The linens and bedding were incredibly comfortable.
The location is right on the orange line easy to find as far as metro transportation. Felt very safe in the neighborhood and the host was incredibly friendly and helpful.
Next time around, we want to try the little restaurant right on the corner, which was always packed and looked amazing.
We enjoyed our 5x-night stay with Drew and would consider…
We enjoyed our 5x-night stay with Drew and would consider staying again.
Among the unit’s positives:
— While the location (mere feet from busy/noisy Mass. Ave.) has some down-sides, the unit is easy walking/driving distance from everything. Mass. Ave. noise is quite noticeable in the living/dining space, but extremely thick doors block noise from the bedroom; no issues sleeping.
— The unit is generally well-appointed (pictures do it justice) and spacious.
— The bed is extremely comfortable.
— The host (Drew) is very communicative, prompt, and check-in instructions were straightforward/timely.
There were a couple of negatives:
— Mystifyingly, one of the light switch panels (controlling all living/dining room lights) worked only from 7:00p - 7:00a. Throughout our stay we (and Drew’s team) trouble-shot this issue repeatedly, but to no avail. No other electrical issues.
— We used SpotHero for parking (avg’ing ~$30/night); would be nice if a spot was included.
Really comfortable bed!! Love the location. Walkable distance to everything.
Really comfortable bed!! Love the location. Walkable distance to everything.
I would stay here again. It was a lovely building, beautiful apartment all the furnishings one could want.
Positive:
The building was beautiful. The apartment was also very beautiful had historic charm. The bed was extremely comfortable. Bathroom was remodeled and lovely. Didn’t get a chance to use the kitchen, but it looked like it would be a great place to stay for for a full week.
Negative:
The air conditioner in the main part of the apartment didn’t get cold, but the one in the bedroom did work well enough to cool down the entire apartment, which was nice.
Also, even though the building was nice the neighborhood might’ve been near one that’s not so desirable because the evenings were filled with a lot of vagrants and loud drunk conversations.
The apartment is wonderfully cozy and tastefully decorated, with a…
The apartment is wonderfully cozy and tastefully decorated, with a comfortable bed and sofa that made us feel right at home. It was spotless, and the host was incredibly responsive and helpful. Parking is just a quick 4-minute walk away at Stanhope Garage. We loved starting our mornings with delicious breakfasts at The Farmers Horse. We often walked to downtown, but there's also convenient public transportation nearby if you prefer.
Drew was a very great host. My wife and I…
Drew was a very great host. My wife and I needed a weekend getaway for just the two of us & this place gave us all we needed. Everything was simply explained and Drew was very responsive when we had questions. The place is as beautiful as the pictures. Parking was the only dilemma, not a huge dilemma. There just wasn’t any designated parking but we were lucky enough to find a park that was accessible right in front of the building, so it worked out. I would definitely recommend a visit here and my wife and I are already planning to come back soon.