The Chester: Urban Luxury, Modern Design
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Boston
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Apartment
2
Guests
1
Bedroom
1
Bathroom
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. Bay windows offer stunning Back Bay views, and the expertly curated decor adds a stylish touch. Book this unique Boston experience today!
Rooms and Beds
Primary
queen beds: 1
Shared space
sofa beds: 1
Full Bathroom 1
Features and Amenities
Kitchen
Suitable for infants (under 2 years)
Suitable for children (2-12 years)
Mini fridge
Wireless Internet
Towels provided
TV
Smoke detector
Shower gel
Shampoo
Refrigerator
Microwave
Rates and Availability
Taxes and fees are additional
Reviews
Drew’s listing was just as described, lots of proactive communication…
June 12, 2025
Drew’s listing was just as described, lots of proactive communication made check in a breeze. Very comfortable stay. certainly would stay again if I was in that neck of the woods.
Had an excellent stay thanks to Drew’s gracious, friendly and…
May 31, 2025
Had an excellent stay thanks to Drew’s gracious, friendly and prompt help. Much appreciated!
My baseline for rating a place is, will I stay…
May 12, 2025
My baseline for rating a place is, will I stay here again and in this case, I will definitely do so. I’ve stayed in other apartments in the Southend and this place was by far nicer, cleaner and in a great location. Very clean, comfortable bed, nice light indoor/outdoor, great neighborhood. It’s an older building and with that comes less noise insulation, but I knew to expect that, I wanted a Boston neighborhood experience where I could walk daily to the event I was attending. Drew was very responsive and friendly in his communication.
Drew was an amazing host! He was always available for…
May 3, 2025
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!
Save 5% on weekly and 10% on monthly stays!
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Other rooms you may like
Drew’s listing was just as described, lots of proactive communication…
June 12, 2025
Drew's listing was just as described, lots of proactive communication made check in a breeze. Very comfortable stay. certainly would stay again if I was in that neck of the woods.
Had an excellent stay thanks to Drew’s gracious, friendly and…
May 31, 2025
Had an excellent stay thanks to Drew’s gracious, friendly and prompt help. Much appreciated!
My baseline for rating a place is, will I stay…
May 12, 2025
My baseline for rating a place is, will I stay here again and in this case, I will definitely do so. I've stayed in other apartments in the Southend and this place was by far nicer, cleaner and in a great location. Very clean, comfortable bed, nice light indoor/outdoor, great neighborhood. It's an older building and with that comes less noise insulation, but I knew to expect that, I wanted a Boston neighborhood experience where I could walk daily to the event I was attending. Drew was very responsive and friendly in his communication.
Drew was an amazing host! He was always available for…
May 3, 2025
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!
Great location in a cozy space. The space is a…
March 13, 2025
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.
Drew’s place is pristine and super clean! The location was…
December 10, 2024
Drew's place is pristine and super clean! The location was perfect for transportation, dinning and walking.
I would come back in a nanosecond. The only rub…
November 21, 2024
I would come back in a nanosecond. The only rub was that I couldn't figure out how to get in the front door when I arrived BUT THAT IS ON ME! (I was really stupid--the pad illuminates when you touch it. In any case, Drew responded to my question instantly.) I was really happy there and wish I'd known about this place earlier, as I had stayed elsewhere a couple of times when I was visiting the area. I will return! THANK YOU DREW.
This was a great place to stay on my trip…
November 12, 2024
This was a great place to stay on my trip to Boston. It’s in a great neighborhood with lots of good shopping, restaurants, and coffee shops. The AirBnB had everything I needed for a short stay with a little kitchenette(including an electric burner to cook small things). Everything was very clean and was nice to have a desk and an additional living space with couch.
Great place with a great location. It has all of…
November 2, 2024
Great place with a great location. It has all of the amenities that you need. Would highly recommend.
Negative: El codigo de entrada al edificio dejo de funcionar…
October 15, 2024
Negative:
El codigo de entrada al edificio dejo de funcionar y no existe un telefono de emergencia donde llamar. Tuve que esperar respuesta luego de enviar un mail, pero mi computador estaba en n la habitación. Debiera haber un telefono de emergencia donde llamar. El sistema de mensajería nunca respondió
Drew has a DARLING little south end gem with this…
October 9, 2024
Drew has a DARLING little south end gem with this one! The building was beautiful, apartment was clean and the perfect amount of space for two. Probably the largest bathroom I’ve come across in the south end of boston which is perfect for a girls weekend with more than enough room for everyone to comfortably get ready! Located above one of my favorite Italian spots (Mida) and by countless coffee/lunch cafes, close to downtown, the esplanade, etc this was perfect for my long weekend visit. I’ll certainly be back!
100% recommend. We slept 2 people so plenty of room….
September 18, 2024
100% recommend. We slept 2 people so plenty of room. The place matched the photos and was extremely clean! Came with linens, plenty of towels, hand soap, shampoo, conditioner, and body gel. The kitchenette would be perfect for a light fare or reheat anything you need. We found free parking three streets over per Drew’s suggestion! After that, we walked and took the subway (which you can Apple Pay to get on for roughly $2-$3 per 1 way) everywhere! It was central and always had a lively atmosphere to make you feel comfortable at night. The listing had a noise warning but we weren’t bothered at all. The stairs are what it says so as long as you are able to do them then this is the place for you!
Great, new place in a wonderful neighborhood of Boston. Would…
September 11, 2024
Great, new place in a wonderful neighborhood of Boston. Would stay again.
We were happy to find this location was available for…
August 28, 2024
We were happy to find this location was available for our visit. Drew was responsive to our questions and provided clear “check-in” instructions. The location was easy to find and access. This is a fourth floor walk up, so take that into consideration if you have mobility issues. We were fine with it, but it is an old brownstone and the stairs are steep and winding.
The room was exactly as described. It was two rooms, a main with bed and side room with a sitting area and TV. The space was perfectly clean, the bathroom was pristine. The only thing noticed was that there was makeup on the pillow cases, which made us wonder if the sheets had been laundered and changed.
We were overall happy with this location and would stay here again. It was on a Main Street, with several walkable bars, restaurants, coffee shops and convenience stores.
Nice Modern Place. Bed was comfy and nice big bathroom….
August 1, 2024
Nice Modern Place. Bed was comfy and nice big bathroom.
Drew was very responsive and was a great host
Our stay in Drew’s cozy apartment was absolutely delightful! The…
July 24, 2024
Our stay in Drew's cozy apartment was absolutely delightful! The place was exactly as pictured - clean, bright and tastefully decorated. The location couldn't have been better, just a short walk from great restaurants and shops. For dinner, I recommend Ilona Restaurant around the corner.
Drew is pleasant to work with, he is responsive and…
July 22, 2024
Drew is pleasant to work with, he is responsive and prompt, always ready to help. The place is clean and just like pictures on the website. The location is convenient and we’d love to stay here again when we visit Boston.
great experience .. was very comfortable .. will come back
July 1, 2024
great experience .. was very comfortable .. will come back
Description
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. Bay windows offer stunning Back Bay views, and the expertly curated decor adds a stylish touch. Book this unique Boston experience today!
Space
Welcome to this meticulously renovated one-bedroom apartment, seamlessly blending modern comfort with historic charm.
Step into the bedroom area adorned with character and custom decor which features a plush queen bed and writing desk.
The living room features a queen pull-out couch, ensuring comfort or extra space for guests. Step into the living room which features character and custom decor, a dining table, a pull-out queen sofa, and two arm chairs. The bedroom features a plush queen bed ensuring a restful night’s sleep.
The kitchenette beckons with its sleek design and practical amenities, including a mini-fridge, microwave, sink, single burner induction cooktop, and drip coffee pot, catering to your culinary needs.
Refresh and rejuvenate in the bathroom featuring classic tile and a glass-enclosed stand-up shower, adding a touch of luxury to your stay.
The living area boasts beautiful wood floors and is adorned with large bay windows offering panoramic views of Back Bay and the Prudential Center, complemented by the elegance of antique rugs, creating a captivating backdrop for relaxation.
For entertainment, indulge in your favorite shows or movies on the smart TV, providing endless entertainment options.
Other things to get excited about:
-Completely renovated space
-100% cotton linens and hotel quality towels
-Wicked fast wifi!
-Smart TV’ in the living room and bedroom
-Hardwoods throughout with tile in the bathroom
-Central heat and air conditioning
-Luxury Soap product, The Botanist and The Chemist by La Botegga
-Fourth floor suite, about 15 steep stairs to reach the front door and about thirty stairs to reach the fourth floor.
Step into the bedroom area adorned with character and custom decor which features a plush queen bed and writing desk.
The living room features a queen pull-out couch, ensuring comfort or extra space for guests. Step into the living room which features character and custom decor, a dining table, a pull-out queen sofa, and two arm chairs. The bedroom features a plush queen bed ensuring a restful night’s sleep.
The kitchenette beckons with its sleek design and practical amenities, including a mini-fridge, microwave, sink, single burner induction cooktop, and drip coffee pot, catering to your culinary needs.
Refresh and rejuvenate in the bathroom featuring classic tile and a glass-enclosed stand-up shower, adding a touch of luxury to your stay.
The living area boasts beautiful wood floors and is adorned with large bay windows offering panoramic views of Back Bay and the Prudential Center, complemented by the elegance of antique rugs, creating a captivating backdrop for relaxation.
For entertainment, indulge in your favorite shows or movies on the smart TV, providing endless entertainment options.
Other things to get excited about:
-Completely renovated space
-100% cotton linens and hotel quality towels
-Wicked fast wifi!
-Smart TV’ in the living room and bedroom
-Hardwoods throughout with tile in the bathroom
-Central heat and air conditioning
-Luxury Soap product, The Botanist and The Chemist by La Botegga
-Fourth floor suite, about 15 steep stairs to reach the front door and about thirty stairs to reach the fourth floor.
Notes
We look forward to welcoming you soon!
Standard rules like no smoking, no partying, no pets, and being respectful of the neighbors apply. Locals and stays 21+ night require ID and proof of stay, inquire for more details!
No sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.
Standard rules like no smoking, no partying, no pets, and being respectful of the neighbors apply. Locals and stays 21+ night require ID and proof of stay, inquire for more details!
No sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.
Neighborhood
The South End of Boston is one of the city's most vibrant neighborhoods, making it an ideal place to settle for the week!
Located on Mass Ave in Chester Square, your stay at The Chester offers easy access to exploring Boston, including the local bus, Mass Ave T stop off the Orange Line, and Silver Line on Washington Street—perfect for exploring.
The area is known for its exceptional dining, with top restaurants including favorites just outside your door like SRV and Mida.
The neighborhood also boasts a rich cultural scene with numerous art galleries and the Boston Center for the Arts. Beautiful green spaces like the Southwest Corridor Park and historic Victorian architecture add to the charm.
Additionally, you'll have easy access to the Boston Marathon finish line, Boston Medical Center, Boston Public Garden, Fenway Park, Newbury Street, the Prudential Center, and more.
Located on Mass Ave in Chester Square, your stay at The Chester offers easy access to exploring Boston, including the local bus, Mass Ave T stop off the Orange Line, and Silver Line on Washington Street—perfect for exploring.
The area is known for its exceptional dining, with top restaurants including favorites just outside your door like SRV and Mida.
The neighborhood also boasts a rich cultural scene with numerous art galleries and the Boston Center for the Arts. Beautiful green spaces like the Southwest Corridor Park and historic Victorian architecture add to the charm.
Additionally, you'll have easy access to the Boston Marathon finish line, Boston Medical Center, Boston Public Garden, Fenway Park, Newbury Street, the Prudential Center, and more.
Features and Amenities
Kitchen
Suitable for infants (under 2 years)
Suitable for children (2-12 years)
Mini fridge
Wireless Internet
Towels provided
TV
Smoke detector
Shower gel
Shampoo
Refrigerator
Microwave
Laptop friendly workspace
Air conditioning
Hot water
Heating
Hair dryer
Fire extinguisher
Essentials
Dryer in common space
Cookware
Conditioner
Coffee maker
Coffee
Body soap
Bed linens