What Our Guests Are Saying

Loved this Airbnb! Would recommend to anyone looking to spend some time in Boston. It was perfect.

What a beautiful stay. 🙂 Drew was easy to communicate with and space was exactly as described. Truly stunning!

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!

Great place to stay and so cute, loved staying here!

Best place!

Great location and matched the description/photos.

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 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!

Drew’s place is pristine and super clean! The location was perfect for transportation, dinning and walking.

Drew’s place was as advertised in the pictures and definitely can recommend this place to others.

Drew was an amazing host! He was always available for answering questions and promptly replied to my messages. The Chester is a lovely building and the rental rooms lovingly and carefully restored but also modernized. And, The Chester is located near wonderful restaurants all within walking distance.I heartedly recommend Drew and The Chester!

Positive: The room – great ambiance, furniture, amenities. The location – walkable, and close to transit Negative: Slightly too much noise from the outside, sound-proof windows would go a long way

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 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.

We loved staying at Drew’s place for the weekend. It was in a great location- walkable, peaceful! I recommend staying here!

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!

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.

Great location in a cozy space. The space is a bit small but the amenities including the spacious bathroom, smart tvs, and fast Wi-Fi more than make up for it. It’s also very quiet despite being on a busy street which was also a major plus. The bed’s a bit firm but was comfortable after I got used to it. Would recommend this place for anyone looking to stay for a weekend or two.

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!

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!

Awesome place! Well cleaned, great communication easy to get in

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!

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!

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.