The Chester: Hip, Renovated, South End
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        Boston
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        Apartment
4
Guests
        
    
        
        
        
        
        
                
                
                        0
Studio
        
    
        
        
        
        
        
                
                
                        1
Bathroom
        
    
        
        
        
        
        
                
                
                        Discover The Chester, A Boutique Stay in the heart of the South End.  Relax in a luxurious king-size four-poster bed or accommodate guests on the queen lay flat sofa. Enjoy the living area with a Smart TV and kitchenette equipped for convenience. Expertly designed with restored historic details, painted wood floors, and beautiful rugs, this retreat exudes sophistication. Tucked away off the street, enjoy tranquility while being close to all Boston has to offer.
Rooms and Beds
Studio
 king beds: 1
Full Bathroom 1
Features and Amenities
                        Hangers                    
        
        
    
        
        
        
        
        
                
                
                                                Internet                    
        
        
    
        
        
        
        
        
                
                
                                                Carbon monoxide detector                    
        
        
    
        
        
        
        
        
                
                
                                                Washer in common space                    
        
        
    
        
        
        
        
        
                
                
                                                Mini fridge                    
        
        
    
        
        
        
        
        
                
                
                                                Iron                    
        
        
    
        
        
        
        
        
                
                
                                                Wireless Internet                    
        
        
    
        
        
        
        
        
                
                
                                                Towels provided                    
        
        
    
        
        
        
        
        
                
                
                                                TV                    
        
        
    
        
        
        
        
        
                
                
                                                Smoke detector                    
        
        
    
        
        
        
        
        
                
                
                                                Shampoo                    
        
        
    
        
        
        
        
        
                
                
                                                Refrigerator                    
        
        
    
        
        
        
        
        
                
                
                        Rates and Availability
Taxes and fees are additional
        
        
        
                
                
            
        
    
Reviews
Great location near our daughter’s apartment
October 29, 2025
	
				
			
				
	
		
		Great location near our daughter’s apartment. Apartment was clean and quiet except for occasional noise from other residents or cars – it is an urban location so that’s to be expected. Ample coffee and creamers provided. This apartment would be tough for anyone with mobility issues – there is no lift and doors to front step and up to 2nd floor are steep and somewhat uneven. We thought it was great and would stay here again!
	
	
				
	
	
				
			
				
	
				
	
		
		Great place, and Drew was a great host
September 20, 2025
	
				
			
				
	
		
		Great place, and Drew was a great host. It was exactly what we needed.
	
	
				
	
	
				
			
				
	
				
	
		
		非常感谢
September 10, 2025
	
				
			
				
	
		
		非常感谢
	
	
				
	
	
				
			
				
	
				
	
		
		
						
							
						
						Save 8% on weekly and 10% on monthly stays!					
				
				
				
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        Other rooms you may like
Great location near our daughter’s apartment
October 29, 2025
	
				
			
				
	
		
		Great location near our daughter’s apartment. Apartment was clean and quiet except for occasional noise from other residents or cars - it is an urban location so that’s to be expected. Ample coffee and creamers provided. This apartment would be tough for anyone with mobility issues - there is no lift and doors to front step and up to 2nd floor are steep and somewhat uneven. We thought it was great and would stay here again!
	
	
				
	
	
				
			
				
	
				
	
		
		Great place, and Drew was a great host
September 20, 2025
	
				
			
				
	
		
		Great place, and Drew was a great host. It was exactly what we needed.
	
	
				
	
	
				
			
				
	
				
	
		
		非常感谢
September 10, 2025
	
				
			
				
	
		
		非常感谢
	
	
				
	
	
				
			
				
	
				
	
		
		Great. A nice change from standard hotel rooms
September 4, 2025
	
				
			
				
	
		
		Positive:
Comfortable stay. 
The room is actually a small apartment, homy and nicely decorated. 
As such, key pad and virtual front desk or no elevator.
	
	
				
	
	
				
			
				
	
				
	
		
		Elegant and convenient apartment in the heart of Back Bay – easy access to restaurants
August 27, 2025
	
				
			
				
	
		
		Elegant and convenient apartment in the heart of Back Bay - easy access to restaurants, live music, shopping, and public transportation - with a friendly and responsive host.
	
	
				
	
	
				
			
				
	
				
	
		
		We love our stay here
August 7, 2025
	
				
			
				
	
		
		We love our stay here
	
	
				
	
	
				
			
				
	
				
	
		
		We really enjoyed our stay at The Chester. Beautifully decorated…
July 30, 2025
	
				
			
				
	
		
		We really enjoyed our stay at The Chester. Beautifully decorated and very clean. Close to many restaurants, stores and Northeastern U where our daughter attends.
	
	
				
	
	
				
			
				
	
				
	
		
		We had such a wonderful stay! I was amazed at…
July 14, 2025
	
				
			
				
	
		
		We had such a wonderful stay! 
I was amazed at how beautiful the area was and there was so much to do just a short walk away. 
The space was gorgeous and had everything we needed. I will definitely book one of Drew’s spaces when we are in Boston again.
	
	
				
	
	
				
			
				
	
				
	
		
		It was a lovely well kept place in a great…
June 13, 2025
	
				
			
				
	
		
		It was a lovely well kept place in a great area and Drew was a great host!
	
	
				
	
	
				
			
				
	
				
	
		
		Beautiful, clean apartment, in a great location, everything was perfect!…
June 5, 2025
	
				
			
				
	
		
		Beautiful, clean apartment, in a great location, everything was perfect! I would definitely stay again. The host also communicated really well.
	
	
				
	
	
				
			
				
	
				
	
		
		This place was charming and very clean. Also it is…
May 29, 2025
	
				
			
				
	
		
		This place was charming and very clean. Also it is a great location. We had at Drew’s apartment everything what we needed during our stay in Boston. The lovely family memorial weekend getaway!
	
	
				
	
	
				
			
				
	
				
	
		
		Charming comfortable apartment in a great location.
May 24, 2025
	
				
			
				
	
		
		Positive:
The location was perfect; it was less than 10 minutes away from Northeastern University where I had an event. The room was beautifully appointed and tastefully furnished. Very gracious space. Quiet, too.
	
	
				
	
	
				
			
				
	
				
	
		
		Great location and matched the description/photos.
March 19, 2025
	
				
			
				
	
		
		Great location and matched the description/photos.
	
	
				
	
	
				
			
				
	
				
	
		
		Comfort and convenience in Boston’s South End
November 23, 2024
	
				
			
				
	
		
		Positive:
Walkability within the neighbourhood and district :several  restaurants, also the wine emporium, Flour.  
Within walking distance of MFA, Boston Public Library. Google maps street view helpful for planning. 
 The 202 unit is set up for success to dine at home on takeout in terms of location - 2 good restaurants within  a 2-4 minute walk and dinnerware - white china for everyday, wedgwood for special evenings.
We appreciated and liked the round table and green chairs. Comfy bed. 
Managers were pretty responsive to text enquiries even tho they weren't able to resolve issues. 
The Victorian interior - reminiscent of a house we once owned!  
Wallys jazz club very close!
Negative:
A. There is no bedside lighting which meant  1. reading in bed wasn’t easy and 2. one has to turn off the overhead lighting using the switch by the door which meant getting out of bed to do that, then finding ones way in the dark to get back to the bed. B. the washcloths are too thick! C loss of internet on the last day and night which cost us mucho $ for roaming fees.
	
	
				
	
	
				
			
				
	
				
	
		
		This was a very charming place – clean and tastefully…
October 30, 2024
	
				
			
				
	
		
		This was a very charming place - clean and tastefully decorated.  The bed was very comfortable.  If you can't handle climbing steep stairs with luggage, this isn't the right choice. Unfortunately, when we arrived, there was a questionable character sitting on the outside stairs up to the apartment that harassed us a bit, which was a little unsettling.  The street isn't bad, but it's close to a sketchy part of town.  However, the location was ideal for being walkable to where we needed to be, and we would choose to stay here again.  That's just the reality of Boston, and Boston is also expensive.  It's nice to have a King size bed choice!
	
	
				
	
	
				
			
				
	
				
	
		
		Great location, very beautiful decorated, has minimal kitchen supplies and…
October 7, 2024
	
				
			
				
	
		
		Great location, very beautiful decorated, has minimal kitchen supplies and induction hot plate to get through breakfast needed. 
Check-in process is a little confusing, front door code wasn’t working, has to go through the basement/back door. Be cautious of hot water stopped working early morning. Woke up without any hot water on Tuesday.
	
	
				
	
	
				
			
				
	
				
	
		
		Beautifully kept and located space to spend a few days….
September 20, 2024
	
				
			
				
	
		
		Beautifully kept and located space to spend a few days. Super convenient walking to many coffee shops, bakeries, and restaurants. Quaint part of town. 
Bed and linens very comfortable. Bathroom clean and spacious for a studio. Kitchenette has everything you need, including a cooktop which was an unexpected perk. 
Definitely recommend staying here.
	
	
				
	
	
				
			
				
	
				
	
		
		Gran Ubicacion
September 10, 2024
	
				
			
				
	
		
		A
	
	
				
	
	
				
			
				
	
				
	
		
		Drew’s apartment is incredible. It felt like Paris. Meticulous and…
September 5, 2024
	
				
			
				
	
		
		Drew’s apartment is incredible. It felt like Paris. Meticulous and stately interior design. Incredible comfy bed. Convenient to Northeastern University. We’ll stay here again.
	
	
				
	
	
				
			
				
	
				
	
		
		We had a lovely stay at Drew’s place! It was…
August 28, 2024
	
				
			
				
	
		
		We had a lovely stay at Drew's place! It was exactly as described. We especially loved the vibe of the place and how clean and stocked it was. We felt very secure with the lock on our door as well as to the main entrance. We checked in earlier which caused the lock code to not work right away, however, Drew was very responsive in helping us to be able to check in and enter the building with no issue! I would highly recommend this place specifically and any of his listings in the future! Thank you for a wonderful stay!!
	
	
				
	
	
				
			
				
	
				
	
		
		This place was exactly as advertised: new and updated re-model…
August 23, 2024
	
				
			
				
	
		
		This place was exactly as advertised: new and updated re-model with some of the original architecture and design.  It was fresh, clean and roomy.  The bed and linens were comfortable too.  Will definitely book for next time.
	
	
				
	
	
				
			
				
	
				
	
		
		Positive: Great location, beautiful renovation, plenty of light, very comfortable…
July 29, 2024
	
				
			
				
	
		
		Positive:
Great location, beautiful renovation, plenty of light, very comfortable bed, lovely furnishings.
Negative:
It would be nice to have a dresser in which to store clothes.
	
	
				
	
	
				
			
				
	
				
	
		
		Clean and comfy! The place was as described, easy to…
July 15, 2024
	
				
			
				
	
		
		Clean and comfy!  The place was as described, easy to get to and Drew was great.  Parking was expensive but that has nothing to do with the place.  The T station was just a few blocks and an easy ride.  Overall it was great!
	
	
				
	
	
				
			
				
	
				
	
		
		Description
Discover The Chester, A Boutique Stay in the heart of the South End. Relax in a luxurious king-size four-poster bed or accommodate guests on the queen lay flat sofa. Enjoy the living area with a Smart TV and kitchenette equipped for convenience. Expertly designed with restored historic details, painted wood floors, and beautiful rugs, this retreat exudes sophistication. Tucked away off the street, enjoy tranquility while being close to all Boston has to offer.
Space
Step into a meticulously renovated space adorned with intricate restored details creating an inviting ambiance throughout. Unwind in the luxurious king-size four-poster bed or accommodate additional guests on the comfortable queen pull-out sofa in the den.
The living area invites relaxation, complete with a Smart TV for streaming your favorite shows and movies. Delight in the convenience of a kitchenette equipped with essential appliances, including a drip coffee pot, microwave, sink, mini-fridge, and induction cooking surface.
Expertly interior designed, this studio exudes sophistication and style, with painted wood floors and large beautiful rugs enhancing the cozy and elegant atmosphere.
Located off the street, enjoy a quiet retreat from city life while still being close to all that Boston has to offer. Experience the perfect blend of historic charm and modern comfort in this captivating studio plus den retreat.
Other things to get excited about:
-Completely renovated space
-100% cotton linens and hotel quality towels
-Gorgeous bathroom with stand up shower
-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
-Second floor suite, about 15 steep stairs to reach the front door and about 10 stairs to reach the 2nd floor.
        
        
        
    The living area invites relaxation, complete with a Smart TV for streaming your favorite shows and movies. Delight in the convenience of a kitchenette equipped with essential appliances, including a drip coffee pot, microwave, sink, mini-fridge, and induction cooking surface.
Expertly interior designed, this studio exudes sophistication and style, with painted wood floors and large beautiful rugs enhancing the cozy and elegant atmosphere.
Located off the street, enjoy a quiet retreat from city life while still being close to all that Boston has to offer. Experience the perfect blend of historic charm and modern comfort in this captivating studio plus den retreat.
Other things to get excited about:
-Completely renovated space
-100% cotton linens and hotel quality towels
-Gorgeous bathroom with stand up shower
-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
-Second floor suite, about 15 steep stairs to reach the front door and about 10 stairs to reach the 2nd 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
                        Hangers                    
        
        
    
        
        
        
        
        
                
                
                                                Internet                    
        
        
    
        
        
        
        
        
                
                
                                                Carbon monoxide detector                    
        
        
    
        
        
        
        
        
                
                
                                                Washer in common space                    
        
        
    
        
        
        
        
        
                
                
                                                Mini fridge                    
        
        
    
        
        
        
        
        
                
                
                                                Iron                    
        
        
    
        
        
        
        
        
                
                
                                                Wireless Internet                    
        
        
    
        
        
        
        
        
                
                
                                                Towels provided                    
        
        
    
        
        
        
        
        
                
                
                                                TV                    
        
        
    
        
        
        
        
        
                
                
                                                Smoke detector                    
        
        
    
        
        
        
        
        
                
                
                                                Shampoo                    
        
        
    
        
        
        
        
        
                
                
                                                Refrigerator                    
        
        
    
        
        
        
        
        
                
                
                                                Microwave                    
        
        
    
        
        
        
        
        
                
                
                                                Long term stays allowed                    
        
        
    
        
        
        
        
        
                
                
                                                Laptop friendly workspace                    
        
        
    
        
        
        
        
        
                
                
                                                Kitchen                    
        
        
    
        
        
        
        
        
                
                
                                                Hot water                    
        
        
    
        
        
        
        
        
                
                
                                                Heating                    
        
        
    
        
        
        
        
        
                
                
                                                Hair dryer                    
        
        
    
        
        
        
        
        
                
                
                                                Fire extinguisher                    
        
        
    
        
        
        
        
        
                
                
                                                Essentials                    
        
        
    
        
        
        
        
        
                
                
                                                Dryer in common space                    
        
        
    
        
        
        
        
        
                
                
                                                Conditioner                    
        
        
    
        
        
        
        
        
                
                
                                                Coffee maker                    
        
        
    
        
        
        
        
        
                
                
                                                Coffee                    
        
        
    
        
        
        
        
        
                
                
                                                Body soap                    
        
        
    
        
        
        
        
        
                
                
                                                Bed linens                    
        
        
    
        
        
        
        
        
                
                
                                                Air conditioning                    
        
        
    
        
        
        
        
        
                
                
                         
        
        
        
         
        
        
        
         
        
        
        
         
        
        
        
         
        
        
        
         
        
        
        
         
        
        
        
         
        
        
        
         
        
        
        
         
        
        
        
         
            
            
            
        
         
            
            
            
        
         
            
            
            
        
         
            
            
            
        
         
            
            
            
        
         
            
            
            
        
         
            
            
            
        
        