The Chester: Penthouse One Bedroom
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Apartment
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.
4
Guests
1
Bedroom
1
Bathroom
Rooms and Beds
Common Area
sofa beds: 1
Primary bedroom
king beds: 1
Features and Amenities
Dining table
Body soap
Conditioner
Coffee
Air conditioning
Bed linens
Carbon monoxide detector
Coffee maker
Cookware
Desk
Dishes and silverware
Dryer in common space
Rates and Availability
Save 5% on weekly and 10% on monthly stays!
Taxes and fees are additional
Location
Reviews
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.
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.
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 Chester: Penthouse One Bedroom
-
Apartment
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.
4
Guests
1
Bedroom
1
Bathroom
Save 5% on weekly and 10% on monthly stays!
Total
Price Details
When
Save 5% on weekly and 10% on monthly stays!
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.
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.
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.
Really comfortable bed!! Love the location. Walkable distance to everything.
Really comfortable bed!! Love the location. Walkable distance to everything.
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.
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.
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!
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
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 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.
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.
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!☺️
Absolutely beautiful space!
Absolutely beautiful space!
Great location and lovely interior design.
Great location and lovely interior design.
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!
Description
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.
Space
Step into our premier apartment suite and embrace the abundant natural light that highlights the restored historic features dating back from the mid 1800’s. Unwind in the inviting atmosphere created by the large windows, indulging in moments of peace and tranquility.
The bedroom features a king-sized bed and a cozy nook with a full-sized writing desk, perfect for working from home. The living area with a layflat sofa and two side chairs, and there's ample seating for everyone. The rooms have been meticulously designed and decorated to ensure your utmost comfort.
The full-sized eat-in kitchen, adjacent to the living room, is ideal for hosting meals. It features elegant wainscoting and classic decor that enhance the room's appeal. The kitchen, fully renovated with a modern oven/stove combo, microwave, refrigerator, drip coffee pot, marble countertops, and custom cabinetry, offers both functionality and style.
Enjoy a comfortable evening streaming your favorite TV shows on the large smart tv's located in both the living room and bedroom .
Other things to get excited about:
-Completely renovated space
-Gorgeous bathroom with stand up shower
-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
-First floor suite, about 15 steep stairs to reach the front door.
The bedroom features a king-sized bed and a cozy nook with a full-sized writing desk, perfect for working from home. The living area with a layflat sofa and two side chairs, and there's ample seating for everyone. The rooms have been meticulously designed and decorated to ensure your utmost comfort.
The full-sized eat-in kitchen, adjacent to the living room, is ideal for hosting meals. It features elegant wainscoting and classic decor that enhance the room's appeal. The kitchen, fully renovated with a modern oven/stove combo, microwave, refrigerator, drip coffee pot, marble countertops, and custom cabinetry, offers both functionality and style.
Enjoy a comfortable evening streaming your favorite TV shows on the large smart tv's located in both the living room and bedroom .
Other things to get excited about:
-Completely renovated space
-Gorgeous bathroom with stand up shower
-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
-First floor suite, about 15 steep stairs to reach the front door.
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
Dining table
Body soap
Conditioner
Coffee
Air conditioning
Bed linens
Carbon monoxide detector
Coffee maker
Cookware
Desk
Dishes and silverware
Dryer in common space
Essentials
Fire extinguisher
First aid kit
Hair dryer
Hangers
Heating
Hot water
Internet
Kitchen
Laptop friendly workspace
Long term stays allowed
Microwave
Oven
Refrigerator
Shampoo
Shower gel
Smoke detector
Stove
Toaster
Towels provided
TV
Washer in common space
Wireless Internet