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
Bedroom
Living room
Features and Amenities
Rates and Availability
Taxes and fees are additional
Location
Reviews
My family & I stayed at Drew’s place on the
My family & I stayed at Drew’s place on the final leg of our summer vacation to Cape Cod and Boston. The place is super spacious, incredibly comfortable, and well-appointed. Although parking is not included, we got lucky and found street parking on the block overnight both nights we were in town.
I’m a little surprised that none of the other reviews mention the noise: Massachusetts Ave is a pretty major street, and there is a hospital a few blocks away – I felt like we heard a lot of noise from sirens, and traffic in general. The unit is not a penthouse; it’s actually the first floor, up one flight of stairs from the street. The noise isn’t too bad in the bedroom, which is located in the back of the unit. But I think it’s worth noting if guests are planning on using the sofa bed, located in the front overlooking the street.
Obviously this isn’t at all a reflection on Drew, who was a great host and very communicative, which I really appreciate. Overall, the place is fabulous.
I’m a little surprised that none of the other reviews mention the noise: Massachusetts Ave is a pretty major street, and there is a hospital a few blocks away – I felt like we heard a lot of noise from sirens, and traffic in general. The unit is not a penthouse; it’s actually the first floor, up one flight of stairs from the street. The noise isn’t too bad in the bedroom, which is located in the back of the unit. But I think it’s worth noting if guests are planning on using the sofa bed, located in the front overlooking the street.
Obviously this isn’t at all a reflection on Drew, who was a great host and very communicative, which I really appreciate. Overall, the place is fabulous.
Drew’s place was gorgeous, clean and walkable to all we
Drew’s place was gorgeous, clean and walkable to all we wanted to do in Boston during our short stay. Loved it, highly recommend!
We loved our stay at The Chester! Drew was very
We loved our stay at The Chester! Drew was very responsive and the unit was exactly as described. 10/10, would stay again!
When
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My family & I stayed at Drew’s place on the
My family & I stayed at Drew's place on the final leg of our summer vacation to Cape Cod and Boston. The place is super spacious, incredibly comfortable, and well-appointed. Although parking is not included, we got lucky and found street parking on the block overnight both nights we were in town.
I'm a little surprised that none of the other reviews mention the noise: Massachusetts Ave is a pretty major street, and there is a hospital a few blocks away - I felt like we heard a lot of noise from sirens, and traffic in general. The unit is not a penthouse; it's actually the first floor, up one flight of stairs from the street. The noise isn't too bad in the bedroom, which is located in the back of the unit. But I think it's worth noting if guests are planning on using the sofa bed, located in the front overlooking the street.
Obviously this isn't at all a reflection on Drew, who was a great host and very communicative, which I really appreciate. Overall, the place is fabulous.
I'm a little surprised that none of the other reviews mention the noise: Massachusetts Ave is a pretty major street, and there is a hospital a few blocks away - I felt like we heard a lot of noise from sirens, and traffic in general. The unit is not a penthouse; it's actually the first floor, up one flight of stairs from the street. The noise isn't too bad in the bedroom, which is located in the back of the unit. But I think it's worth noting if guests are planning on using the sofa bed, located in the front overlooking the street.
Obviously this isn't at all a reflection on Drew, who was a great host and very communicative, which I really appreciate. Overall, the place is fabulous.
Drew’s place was gorgeous, clean and walkable to all we
Drew’s place was gorgeous, clean and walkable to all we wanted to do in Boston during our short stay. Loved it, highly recommend!
We loved our stay at The Chester! Drew was very
We loved our stay at The Chester! Drew was very responsive and the unit was exactly as described. 10/10, would stay again!
Drew’s home was impeccably decorated which is a key need
Drew's home was impeccably decorated which is a key need for me anytime I visit a new city. The details, the finishes, the creative flair—it was all so lovely. I definitely look forward to coming back.
Very beautiful place !!! the most comfortable bed I have
Very beautiful place !!! the most comfortable bed I have ever slept on as well. would recommend to anyone and definitely would stay again!
Nice spot, great stay!
Nice spot, great stay!
Drew was extremely responsive and I had a really great
Drew was extremely responsive and I had a really great experience. The place was obviously extremely beautiful, but what stood out to me is that my check in was 4pm, but I arrived in Boston at 12. He allowed me to leave the luggages in the room whilst its being cleaned. I strongly recommend this stay. I read the 3-4 star reviews, and none of them were accurate. The outside wasn’t loud at all, and the kitchen was completely adequate for people needing to cook.
We had a wonderful stay and easily walked to Newbury
We had a wonderful stay and easily walked to Newbury street and then to Fenway to catch a Red Sox game. We were a family of four so our boys were on the pullout in the living room. There were no printed instructions for the pull it out (which was not obvious) so we had to message the host who sent a video which was helpful. In addition there was no blanket or comforter for the pullout so the kids were not warm the first night. We messaged the host who got a comforter delivered for the second night. The place was in a wonderful location and we had a great time exploring the area.
Cozy with historic charm! Drew’s space was beautiful, decorated to
Cozy with historic charm! Drew’s space was beautiful, decorated to feel luxurious. It was also very clean and comfortable. Walking distance to Back Bay Area and lots of restaurants/shopping.
Drew’s place was perfect for a work/play trip to Boston.
Drew’s place was perfect for a work/play trip to Boston. The apartment is close to a T station, and walking distance from all Boston attractions. There are 2 great restaurants within 50 feet, Mida and Ilona, and Toro is a 10 minute walk. Drew was very responsive and helpful. We would definitely stay again.
Second time staying here and will probably be back again!
Second time staying here and will probably be back again!
The place looked just like the pictures. Drew was a
The place looked just like the pictures. Drew was a fantastic host and very friendly. It was great to have the restaurant Mida right next door. I highly recommend their espresso martini.
It is a very nice place to stay at
It is a very nice place to stay at
Drew was responsive, place was immaculate, and would stay again!
Drew was responsive, place was immaculate, and would stay again!
Drew’s place was amazing! Parking sucks but that’s expected in
Drew’s place was amazing! Parking sucks but that’s expected in this area I learned. Only down side was the loud vacuuming and workers right outside the door, that lasted about an hour mid day when trying to relax. But otherwise perfect!
Beautiful and cozy apartment that’s in the heart of Boston,
Beautiful and cozy apartment that's in the heart of Boston, you really couldn't ask for more! Our host, Drew, was very responsive and helpful with any inquiries that we had. The apartment is also right next to a charming Italian restaurant named "Mida", their food is delicious (I recommend the Mushroom Parpadelle, it was my favorite!). My husband and I hope to come back soon!
One of our favorite stays. Great location, beautiful flat, and
One of our favorite stays. Great location, beautiful flat, and Drew was perfect host. We would highly recommend!
Absolutely gorgeous place. Location was central to many things to
Absolutely gorgeous place. Location was central to many things to do, and provided a great landing zone for us when it was too cold to go out. Drew was very responsive and friendly. Would absolutely stay again!
It was out first time in Boston and we loved
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
Stunning apartment
Great location
Comfortable bed
Lovely bathroom
Would stay again when visiting our children.
Great location
Comfortable bed
Lovely bathroom
Would stay again when visiting our children.
Gorgeous space and communicative host. Great location.
Gorgeous space and communicative host. Great location.
Drew’s place is the perfect New England charm we were
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
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
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 ! Drew’s place was beautiful, and
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! Drew was super informative
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!
Absolutely love Drew’s place! This is our second time staying,
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 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. Drew is
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.
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!
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!
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 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!
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!
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.
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!
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!
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!
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 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
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
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.
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.
Beautiful and convenient
Beautifully decorated, clean, and comfortable! Great location. We walked to Fenway Park and to various restaurants. It was a very easy Uber pickup location since there is a bus stop in front of the home. It was a short inexpensive Uber ride to all the historical sites.
Really comfortable bed!! Love the location. Walkable distance to everything.
Really comfortable bed!! Love the location. Walkable distance to everything.
Perfect Stay in Boston
Absolutely loved my stay. Great location, beautiful place. Clean and bright. We will be back!
I would stay here again. It was a lovely building, beautiful apartment all the furnishings one could want.
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.
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.