Top 11 Airbnb Vacation Rentals In South End, Boston, Massachusetts - Updated 2022

airbnb Boston South End, Usa

The vibrant South End is one of Boston’s most sought-after neighborhoods with its beautiful parks, art galleries and elegant brownstones. A true foodie’s paradise, it’s home to Tremont Street, often dubbed “Restaurant Row”. Conveniently located minutes from Downtown, South End is the largest intact Victorian district in the US and listed in the National Register of Historic Places. Find your perfect brownstone holiday home from this list of the top Airbnb vacation rentals in Boston’s South End, Massachusetts.

1. Stylish downtown studio in the South End (from USD 198)

Experience Boston’s finest by booking a stay in this stylish studio apartment in the city’s South End neighborhood. Its central location offers guests quick and easy access to many of the city’s top restaurants, art galleries, shops, bars, landmarks, and a lot more.

The studio features a cozy queen bed to sleep up to two. It also features one bath, a living area with a couch and cable TV, air-conditioning, heating, Wi-Fi access, a fully equipped kitchen, and a dining area to ensure comfort and convenience.

Stylish Downtown Studio in the SouthEnd, C.Ave# 3
Boston, Massachusetts, United States
245 reviews  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
mostly perfect though the furniture was cheap and wobbly in places and the bed was a little uncomfortable
cozy yet small with nice big windows for a pretty street view
very clean and thoughtful touches
the place was very cozy and very clean
great location clean and easy communication when needed
the place was sparkling clean and the shower had excellent water pressure good location too
close to downtown clean and neat
if the host does resolve it then i would change my advice entirely and heartily recommend it
staff was very responsive and the location is great
great location right by bike rentals
great location and cute apartment
great location & great value
great location and a comfortable studio
the apartment and location are great
Read more reviews

2. Penthouse in South End brownstone (from USD 100)

This penthouse apartment in a brownstone from the 1850s has a bright sunny room ideal for a couple or a solo traveller. The room has a comfy double bed, a flat-screen TV and a view over the beautiful Boston skyline. The fully-equipped kitchen in the shared open plan kitchen/living room area is yours to use, and you’ll also have access to the recently renovated bathroom and a washer-dryer. The whole apartment has a charming feel with its exposed brick walls and hardwood floors. If you’re in Boston to apply for residencies or for an audition, the flat’s location near both Tufts and the Boston Medical College, as well as the major music schools in Boston like Berklee and Boston Conservatory, is more than perfect! The location is also ideal for foodies and tourists as you’re surrounded by great restaurants and not too far from any of Boston’s main attractions such as the Boston Common or the Fenway Park.

Room At The Top - South End Brownstone Penthouse
Boston, Massachusetts, United States
471 reviews Superhost  Wifi Available
Private room in loft 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
this is a beautiful apartment with lofty ceilings
the apartment was stunning and we had everything that we needed
we had a comfortable and enjoyable stay and would highly recommend it
the apartment is classy chic and charming with lots of details from art and cultural history
unit on before you head to bed and you're good
clean and very boston in a hip way
the place was sparkly clean
apartment was clean and better than the pictures
the apartment is really beautiful and the room is clean and cozy
the apartment/room is clean and cozy and beautifully decorated
wonderful hospitality helpful host beautiful apartment
she was so sweet and accommodating
super responsive host
thank you betsy for being a wonderful host
she was very helpful and communicative before we got there
good location too with easy access to public transportation
the location is also perfect
great location and beautiful house
great location and a comfortable room
it’s located in the perfect location to go anywhere in boston
Read more reviews

3. Parlor Room in Montgomery Place (from USD 75)

In the heart of South End, this vacation rental is surrounded by restaurants and art galleries and just a short walk from Copley Square and public transportation. This compact studio flat has a kitchenette with a microwave, hob and kettle, and a spacious full bathroom. In an old brownstone, it has typical hardwood floors and large windows, making the place look bright and airy. Thanks to its comfy queen bed, this studio would be great for a couple or a solo traveller.

Montgomery Place - Parlor Room (Room 2)
Boston, Massachusetts, United States
172 reviews Superhost  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the room was perfect for two with all the amenities we needed
the place really feels like a private appartement with extensive amenities for the bathroom and the kitchenette
plus great shampoo and conditioner in the bathroom
nice room with kitchenette and bathroom
very clean room with amazing touches such as oj yogurts granola great coffee etc
the apartment was clean and cozy
clean affordable and quiet
the place is clean and charming
it was quiet extremely clean and comfortable
it is very clean and in a very beautiful neighbourhood
the host was really helpfull and suggested some nice local restaurant
the hosts were very nice and accommodating
she was really helpful and willing to answer our questions at any time
kathe and lisa are great hosts
she's very quick in response for any questions i have and helpful too
nice appartment located at walking distance from the center
great location in a great neighborhood
great location 10 mins walking to underground station back bay nearby
location is amazing loads of good restaurants around the corner metro is only 5 min walk away
nice spot close to the subway system
Read more reviews

4. Private room in the heart of the South End

This private room in a stylish apartment from the 1900s will let you experience the best Boston has to offer! Situated in the vibrant South End, it’s close to many excellent restaurants, bars and art galleries, and under a ten-minute walk from the Boston Common. The taxi ride from the Logan Airport is about 15-minutes. The kitchen (equipped with all the necessities and more: stove, oven, microwave, toaster, etc.) and the bathroom with its amazing rain head shower are recently renovated and you’ll have full access to both during your stay. There’s also a cute little balcony!

Heart of the South End Near It All! Full condo
Boston, Massachusetts, United States
230 reviews Superhost  Wifi Available
Shared room in rental unit 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
the air mattress is surprisingly comfortable and the privacy screen makes the space feel private
only issues are that we wanted a better bed and a quieter air con
it's comfortable and cosy exactly as described online
a very comfortable place to live in
gorgeous clean and comfortable place
a very clean positive space with a laid back atmosphere
julie’s place is immaculate stylishly and impeccably clean and cozy
the place is clean and so much space
her place was clean and it was like staying with a friend
julie was a fantastic host
julie was an amazing host
julie was a great host
the host is also nice
julie is an amazing host
excellent location in boston that was extremely close to shops restaurants parking
great location good cost
great location next to much of the night life and central to all kinds of cool stuff
location is perfect close of more important places in boston
julie communicated well and the location was good
Read more reviews

5. Private room by Prudential and Back Bay

Just two blocks from the subway, this lovely private room is within walking distance from the historical sites in Boston such as the Quincy Market and most tourist attractions like the Fenway Park. Surrounded by high-end boutiques, bakeries and restaurants, the two-bedroom, two-bathroom apartment is in a Victorian row house with original hardwood floors and an antique fireplace, but has all modern necessities like WiFi and air conditioning (a rarity in Boston). Your private bedroom will have a plush queen bed and a cute reading nook, and the spotless guest bathroom is for your private use only. You’ll have free access to the spacious kitchen and can even use the washer and the dryer in the flat.

South End Room on park by T, Prudential & Back Bay
Boston, Massachusetts, United States
313 reviews
Private room in apartment 1 Bed 1 Bedroom 1 Bathroom

6. Cozy brownstone in a convenient area

The location of this cosy private room is fantastic! Restaurants, shops and the Symphony Hall are all within walking distance, and there is easy public transport access to places like Tufts Medical School, MIT, Harvard, Faneuil Hall, Aquarium and the airport to name just a few. Your room will have a queen-sized bed and a desk, making it perfect for business travelers, solo adventurers or couples. The shared bathroom and kitchen are both spotless and fully-renovated, and there is a coin-operated washer/dryer downstairs to make your stay as comfortable as possible.

Cozy Boston Brownstone, Convenient Area, Easy MBTA
Boston, Massachusetts, United States
224 reviews
Private room in apartment 1 Bed 1 Bedroom 1 Bathroom

7. Sunny downtown apartment

With plants, hardwood floors, ample sunlight, crispy whites and natural colors, this apartment is like a refreshing oasis! In your room, you’ll find a comfy double bed with fresh linen. The bathroom and the open plan kitchen and living room area are shared with the welcoming hosts and their seriously cute pup called Pickle. Surrounded by South End’s many renowned restaurants and close to the Boston Common, the oldest city park in the US, this ideally-located flat also has great public transport access.

Sunny Downtown Apartment
176 reviews
Private room 1 Bed 2 Guests

8. Bright bedroom in prime location

This modern private room is perfect for solo adventurers or business travelers. The location is calm yet central and easily accessible by public transport, Uber or Lyft. You’ll be within walking distance from some of Boston’s finest restaurants, but if you prefer eating in, the kitchen has everything you might need, even a dishwasher. The bedroom is furnished with a comfy bed, a full closet and a desk, and you’ll have full access to both of the bathrooms and common areas.

Bright Boston Bedroom in Prime Location
82 reviews
Private room 1 Bed 2 Guests

9. Private room on garden level in Montgomery Place

This beautiful private room is in an ideally located brownstone right by South End’s many restaurants, parks and boutiques. Copley Square and the Boston Public Library are under a 10-minute walk away, and Boston Common and Public Garden are not much further. The stunning antique furnishings include an oak armoire and a leather reading chair, and the wooden bed is very comfy and luxurious. The room also has a desk and tea making facilities, and your private bathroom is clean and spacious.

Montgomery Place - Garden Level (Room 1)
68 reviews
Private room 1 Bed 2 Guests

10. Luxury one-bedroom apartment with free parking

This lovely flat has one bedroom with a queen bed and a queen-sized sofa bed in the living room, making it fit up to four people. With free parking, a subway station just around the corner and many Boston sights such as the Fenway Park and the Museum of Fine Arts within walking distance, this is the perfect holiday home! The modern kitchen has all you might need, including an oven and a stove as well as a large fridge. The living room area is tastefully furnished with a dining table, two armchairs, a sofa bed and a TV. In the bedroom, you’ll find a luxurious double bed, a small desk and some storage space.

*Luxury2beds*/free parking Boston
Boston, Massachusetts, United States
301 reviews
Entire apartment 2 Beds 1 Bedroom 1 Bathroom

11. Penthouse in South End, Union Park

This sunny penthouse is situated in one of the most sought-after spots in Boston! Right next to South End’s best restaurants and shopping opportunities, it’s within walking distance from the Boston Public Gardens, the Theatre District and Chinatown and has great public transport connections. The luxurious penthouse is tastefully decorated with an original fireplace, a large, recently-renovated bathroom and an immaculately clean kitchen. Your private bedroom has a built-in bookcase, a desk, a closet and a cosy double bed.

Penthouse - South End, Union Park (Back Bay)
Boston, Massachusetts, United States
181 reviews
Private room in condominium 1 Bed 1 Bedroom 1 Bathroom

Culture and fine dining in Boston's South End

Boston is chock-full of history and culture, and staying in vibrant South End will let you experience that first hand! Enjoy some of Boston’s finest restaurants including Toro, B&G Oysters, and Barcelona, admire the historical brownstones and beautiful parks or explore the art galleries and unique boutiques of this elegant neighborhood. With many quintessential Boston sights like the Boston Common and the Copley Square within walking distance and great public transport, South End is definitely one of the best neighborhoods to stay in, whether you’re in Boston for business or pleasure.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Originally from Finland, I grew up in Luxembourg and studied in the UK. I'm an eternal daydreamer and always looking for my next adventure, whether it's sheep herding in Mongolia or getting lost in...Read more

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