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Best HomeAway Vacation Rentals In Boston, Massachusetts - Updated 2020

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Boston is one of the prominent cities in the United States and the largest city of Massachusetts. It plays a vital role in the American Revolution which is well evident in its famous attractions like Freedom Trail and historical locations. This city is honored as the “city of firsts” which includes the first public park, Boston Common, the first subway system in the US, Tremont Street Subway, and the first public school, Boston Latin. With plenty of parks and playgrounds, the city has the reputation of being in the “top ten fittest US cities.” With numerous good things to explore in Boston, it is packed with some of the best accommodations for visitors. Let’s explore the top HomeAway vacation rentals in Boston.

1. A spacious apartment close to attractions

Come and stay on the third floor of an 1890 Victorian home in South Boston and experience the historic greatness of the city. The bus stop is located right at the corner of the house. Subway, restaurants, parks, beach and the Dorchester Heights monument are located in the walkable distance. Major attractions like Freedom Trail, Children’s Museum, Fenway Park, and JFK Library can be accessed within 3 miles (4.8 km) from here. A babysitter is available on-site to take care of your children. This two-bedroom apartment features a king-size bed, double beds, a full-sized futon, and a baby crib.

Spacious, Immaculate, Great Location
159 reviews
Apartment 5 Guests 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
kitchen is perfect for cooking bedrooms are big ac is nice and cold
beds are comfortable and there is lots of space
the place was very clean and the king size bed was very comfortable
said everything was very clean and they loved the location
donna was very accommodating and friendly place was very clean and quiet loved the neighborhood
the property was clean and in a great location
the kitchen and bathrooms are well stocked and clean
love the neighborhood our hosts were so kind and helpful
donna was a fantastic host who made our stay very enjoyable
we were met at the door by max & donna who were great hosts
donna and max are excellent hosts
donna and max are extremely kind and friendly host
the location is great
we loved this location for our two couple vacation
location is ideal for any and all boston activities
great safe neighborhood that has multiple stores and restaurants within a quick walk
it is in a great location- walking distance to shops and restaurants
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2. A splendid 1850s row house (from USD 380)

This historic house is a 1850s brick row house right in the center of Charlestown. Faneuil Hall and Quincy Market are just a few minutes away from the house. There is an espresso machine to serve you hot coffee any time of the day. The high-definition TV is subscribed with a cable package with top channels and Netflix. The house includes a king bed, a queen bed, two single beds, and a double bed in their four bedrooms. You can bring your pets to this accommodation.

1850's Row House on Gas-Lit Street Adjacent to Bunker Hill & Freedom Trail
39 reviews
House 8 Guests 4 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
--the photos do not do it
The kitchen is well stocked for making meals
The third floor has three bedrooms that share a bathroom
It is charming and everything is top quality - bedding furnishings
Wow - that pretty much sums it up
It was spacious and very clean Owners very responsive Fantastic location for sightseeing
Excellent location well maintained beautiful property Owner was available and quick to resolve any issues
Hosts were responsive and check in was so easy
Max and her daughter were extremely helpful with anything we needed and their responses were lightning quick
the manager was very responsive and friendly
We had a wonderful family vacation in Boston with our family of five
CVS and Starbucks within 3 blocks
The location was perfect close to grocery stores and convenience stores
Wonderfully updated maintained row house in historic Charlestown on the Freedom Trail Easy walk to North End
It is in a great location
Property located in the heart of Bunker Hill Walking distance to Bars and Restaurant Short Uber rides to other landmarks and the city Whole Foods
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3. A cozy and clean duplex (from USD 200)

This 1860s two-bedroom apartment is family-friendly and equipped with modern amenities. Located at Jamaica Plain, the house is close to the Jamaica Pond, Arnold Arboretum, and various parks. Just walk for a minute to reach 39 bus downtown and 8 - 10 minutes to get to the Summer Hill area of JP. Floor-to-ceiling, large windows, mahogany porch, and hardwood floors give a beautiful look to the house. A 40 inches HD digital LED TV, free Wi-Fi, and DVD are available for entertainment purpose. Master bedroom has a queen-sized bed and the secondary bedroom includes a twin bed and a bunk bed. A foldable bed with good memory foam mattress is available for an extra person.

Maria's JP Rental - Boston Duplex in Popular Jamaica Plain ("JP") area
107 reviews
Apartment 6 Guests 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
The one bathroom being down stairs was a little challenging as well
2 bedrooms small but comfortable Plenty of extra sleeping space for larger families
That can be frustrating when hauling luggage through the narrow passage to the apartment when the driveway is occupied
The bedroom sizes for both bedrooms good size
The only thing I would be aware of is that the bathroom is downstairs and the bedrooms are upstairs
and I however if you have
But the bathroom was very clean
The home was clean and in a good neighborhood Fresh smelling flowers and quite
Please note that the one bathroom is downstairs with bedrooms upstairs Very satisfied with our stay and can't wait to finish our Boston exploration another time
Maria and John were extremely helpful when needed
Maria is incredibly friendly and attentive as the owner She and her family live right next door so very accessible
She was extremely helpful and kind
Maria and John were great hosts helpful but respectful of our privacy
Maria was very welcoming and made us feel at home
Great location just a 5 minute walk from the main drag where there are great local restaurants and shops and just a 10 min ride on the T to get to Northeastern
It's in a great location in Jamaica Plain--near Centre street--with restaurants stores and markets nearby
Quaint neighborhood and very easy to walk to the train and restaurants
The location of this property is fantastic with lots of restaurants a short walk away
Cozy appartment duplex just outside Boston (15-20 min train ride)
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4. A stunning villa overlooking the harbor (from USD 500)

This wonderful villa overlooks the harbor and vessels. Constitution Beach is at the end of the street. Bicycles are available for sightseeing in the city and kayaks are there for water activity. Numerous shopping options, eateries, museums, parks, and the swan boat ride can be accessed with a few minutes from the house. The kitchen includes a dishwasher, refrigerator, stove, oven, microwave, grill, coffee maker, toaster, blender, coffee grinder, ice maker, lobster pot, and pantry items.

Harborfront Villa, Charming Mix of Contemporary and Turn of the Century Elegance
94 reviews
villa 10 Guests 4 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
but with the view of the airport we didn't miss TV
Our favorite room was the sun room where we enjoyed the view of the Boston skyline
Beautiful home right on the water
(Save the driving hassle and parking expense and take the subway )
The property was very spacious plenty of room for the 7 people we had
The house was very clean
and we were able to sleep comfortably and had everything we needed
The hosts were very helpful and friendly
Nelson was so helpful and responded quickly if we had questions
spacious and well furnished
we're good hosts even providing packnplays for us Would definitely return and recommend
Beds were very comfortable Owners were very quick to respond to all questions and offer recommendations when asked Home was clean and well appointed
The property is very close to the city in a safe neighborhood
makes downtown Boston easily accessible in only a few minutes
the planes are not very loud and not disturbing for sleeping or relaxing A few short blocks to the Blue T subway
lots of games and DVDs and binoculars to view the arrivals and departures at Logan airport located just across the bay
The house is located in such a great spot to be able to get to the city
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5. A beautiful Beacon Hill condo

This 500 square feet (46.4-square meter) condo has an appealing brick structure. Boston Common and Public Garden are just two blocks away from here. Just walk for one block and explore the shops and eateries on Charles Street. The large windows bring ample light into the house which is complemented by the lofty ceilings. This one-bedroom condo has a queen-sized bed and a futon in the living room. Amenities such as air conditioning, TV with cable channels, books, heater, internet, parking, Wi-Fi, iron & board, fireplace are offered here. The kitchen comes with modern appliances to make a gourmet meal.

Beautiful Beacon Hill! Fabulous, historic heart of Boston! Sweet 1-bd condo.
37 River St #2
185 reviews
condo 4 Guests 1 Bedroom 1 Bathroom

6. A lovely and well-connected condo for five

The two-bedroom lovely condo is located on Garrison Street with nearness to the popular attractions of Boston. Boston Public Garden, Boston Symphony Hall, Fenway Park, Charles Playhouse, Copley Square, Mistral, Prudential Center, Boston Public Library, and Skywalk Observatory can be reached within a mile from the house. The master bedroom has a king-sized bed, secondary bedroom has a queen-sized bed and the living room has a sleeper sofa. Amenities such as TV with satellite channels, air conditioning, washer & dryer, heater, internet access, iron & board, elevator, and hair dryer are available here.

Stay Alfred's best in Back Bay
32 Garrison St
115 reviews
condo 5 Guests 2 Bedrooms 2 Bathrooms

7. A retreat in a fabulous location

This classy brick townhouse has a large window to bring natural light into the house. The kitchen is equipped with granite counter top, modern equipment, and stainless steel appliances. Freedom Trail, Faneuil Hall, and public transportation are just minutes away from the house. Flat-screen cable TV and uninterrupted, high-speed internet are available here. The house features a queen-sized bed, two single beds, and a pack-n-play crib. A public parking garage is just a block away from this accommodation.

Little Italy North End Retreat, Fabulous location.
179 Endicott St
91 reviews
condo 6 Guests 2 Bedrooms 2 Bathrooms

8. A luxury condo for six

This gorgeous two-bedroom condo offers a comfortable atmosphere to enjoy a warm vacation in Boston. The luxury condo comes with a 52 inches TV with satellite channels and Wi-Fi service. You can just take a walk to access the notable attractions of Boston like Faneuil Hall, the Statehouse, the Boston Common, Freedom Trail, Frog Pond, Quincy Market, and Charles River Esplanade. The house includes a queen bed and a double bed in the bedrooms along with a double sleeper sofa in the living room.

Luxury in the heart of the North End In Tourist District
65 Salem St 2
91 reviews
condo 6 Guests 2 Bedrooms 2 Bathrooms

9. A sophisticated home for a family

If you are business travelers or just casual vacationers, this two-bedroom condo will be perfect for you. Public transportation is very close to the accommodation. There is an indoor pool which is open all seasons for relaxing and unwinding. Attractions like Boston Children’s Museum, Boston Common, Boston Opera House, Boston Public Garden, Boston Tea Party Ships & Museum, Copley Place, Faneuil Hall, and South Station can be reached within a mile from this condo. This two-bedroom condo includes a king-sized bed, a queen-sized bed, and a sleeper sofa.

Visit Boston Common; the oldest park in the USA
124 reviews
condo 5 Guests 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
I have no doubt the filter needed replacement
As I mentioned the apartment was spacious but was in need of new paint and cleaning of carpets
We did complain but management could not do anything because that apartment belonged to a resident
carpet extremely stained - needs to be replaced Also could use fans in bathrooms and shelving in shower
I opened the air intake to see if there was anything obvious and noticed that the air filter had last been replaced 05/15/2017 (nearly two years ago)
The property was clean and as advertised
Central to everything Very clean and modern
Condo was large although we had air conditioning issues that were fixed but not right away
He was incredibly rude and made our experience terrible as soon as we arrived
We were early and they were not able to check us in and did not offer to take any bags
and they were nice and tried to help
They finally realized the apartment had been checked in and did not tell us
The concierges were friendly and helpful
Just perfect and reasonably priced
There is a subway station steps away CVS and Walgreens
We stayed three nights in this lovely suite Really loved its location it'sright in the heart of Bston downtown walking distance to everything
Great location and a good option for families
Great location close to the train and walking distance from the Common
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10. An upscale three-bedroom accommodation

This stunning three-bedroom apartment is just one block away from Boston Common. Key attractions like Boston Children’s Museum, Boston Public Garden, Boston Tea Party Ships & Museum, Copley Place, and Faneuil Hall are within a walking distance. Erbaluce, BLR by Shojo, Jacob Wirth, and Mike & Patty’s are some of the notable dining options near the house. The master bedroom has a king-sized bed, the second and third bedroom has queen-sized beds and the living room has a futon. A well-equipped kitchen features dishwasher, refrigerator, stove, oven, microwave, coffee maker, toaster, dishes, and utensils.

Make a splash in Stay Alfred's heated indoor pool
119 reviews
condo 7 Guests 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The apartment looked exactly like the pictures
I'm not against it
Room is huge and the view from the balcony is brilliant
Arriving and leaving were super easy
Great location and very roomy apartment for us - family of 6 Unusual setting being an apartment in a apartment building that feels part hotel and part apartment
The bedrooms are clean and the check in process was extremely easy
The unit was large and comfy Location was terrific Close to Boston
Adjacent parking garage exists with liquor store and Walgreens
Beautiful property with amazing views
right next store Had some issues with the Wifi that were fixed after a quick call to the staff
The doorman Chuck gave us suggestions where to get groceries and was very helpful and courteous when our check in was late
The pool was very nice
Great location to walk to just about everywhere in Boston
The building location was perfect as it was steps away from the Orange line and 2 blocks from the Green line
This was a great property Walking distance to almost all majors sites in Boston and close to subway to get further out like Fenway
Wonderful 3 bedroom 2 bathroom condo Easy to get to and great location Can easily walk to many key attractions in Boston
It was located 2 blocks from Boston Commons which was amazing
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Enjoy a perfect vacation in Boston

Whatever the season, there are so many things to see and do in Boston. Stay in the top HomeAway vacation rentals to enjoy the best of the city.

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

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