50 Best Boston Apartments on Holiday Lettings - Condos

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916 Vacation rentals

(1) Good 

6

Vacation apartment in Boston

Massachusetts / Boston

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Air conditioning
Large, bright apartment located steps from Coolidge Corner. 1 bed/1 bath. Fully equipped kitchen with dishwasher. There is also a gym and laundry located in the building. Across the street from a T stop and walking distance to the heart of Coolidge Corner. …see more

Pricing unknown

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4

Vacation apartment in Boston

Massachusetts / Boston

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly
Great one bedroom apartment with lots of living space and large full bathroom. Complete kitchen including dishwasher and microwave. Free internet and cable access. 24 doorman and paid parking available in lower garage. Many nearby restaurants, bars and a Walgreens. Also …see more

from $1,140 / night

$5,700 / week

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from $1,140 / night

4

Vacation home in Boston

Massachusetts / Boston

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
Beautiful one bedroom penthouse apartment with small balcony overlooking Boston harbor and airport. Walk-able to all major tourist destinations including Fanueil Hall and Quincy market. Many nearby restaurants and bars. Right next to the blue and orange line T stops. Do …see more

from $1,266 / night

$6,329 / week

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from $1,266 / night

(1) Excellent 

22

Vacation apartment in Boston

Massachusetts / Boston

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Suitable for children age 5+
  • Car not necessary
  • Air conditioning
Our Historic Beacon Hill, Two bedroom, Queen size beds, duplex Condo, is comfortable and well located. An ideal central location for exploring or working in the heart of Boston at: 27 Ridgeway Lane, Beacon Hill, Boston, 02114. Great Restaurants nearby. Access to ALL p …see more

from $305 / night

$2,135 / week

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Responds fast!
avg. 2 hours 22 minutes

from $305 / night

(2) Excellent 

19

Vacation apartment in Boston

Massachusetts / Boston

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Private 3Bd Condo Near Airport Train Station Boston only minutes to downtown This condo is on two levels. Level 1 has two bedrooms and one full bath (WC, vanity and bathtub), the 3rd bedroom is on basement level with an additional bathroom (WC, vanity and shower). Our …see more

from $345 / night

$2,415 / week

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avg. 2 hours 48 minutes

from $345 / night

24

Vacation apartment in Boston

Massachusetts / Boston

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child friendly
Dazzling city views await during your stay at this stunning, bright and open 5th-floor corner Boston loft apartment near vibrant Chinatown. This beautiful 2-bedroom, 1-bathroom furnished loft apartment in Boston comes complete with a spacious open floor plan, 11-foot c …see more

from $115 / night

$805 / week

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Responds fast!
avg. 2 hours 41 minutes

from $115 / night

23

Vacation apartment in Boston

Massachusetts / Boston

4 12 6 nights min

  • 4 bedrooms
  • sleeps 12
  • 6 nights min
  • Nearest beach 6 mi
  • Child friendly
  • Car not necessary
Completely renovated , duplex apartment in a two family house. Walls of windows, very sunny, and cheerful. There are two units in this house. Unit #2 is on the 2nd and 3rd floors of the house. Unit #2 has four large bedrooms , two and half tiled bath in total . Three …see more

from $450 / night

$2,000 - $10,400 / week

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from $450 / night

(17) Very Good 

24

Apartment rental in Boston

Massachusetts / Boston

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Find Boston Vacation Rentals on FlipKey Find Boston Vacation Rentals on FlipKey Modern apartment in a JP 2 family. Enjoy our extensive collection of fresh local art. This is not your standard run of the mill rental. Collection will occasionally rotate. Currently showing …see more

from $179 / night

$1,150 - $3,550 / week

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Responds fast!
avg. 2 hours 24 minutes

from $179 / night

(53) Excellent 

Certificate of Excellence

14

Vacation condo in Boston

Massachusetts / Boston

1 2 28 nights min

  • 1 bedroom
  • sleeps 2
  • 28 nights min
  • Car not necessary
  • Air conditioning
This fully furnished apartment has a one month minimum rental period. Any rental beyond 3 months will be handled directly by the owner with a standard rental contract. We've been renting high-quality furnished accommodations for over 8 years, exclusively in the Beacon …see more

Certificate of Excellence

from $240 / night

$1,400 / week

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Responds fast!
avg. 3 hours 24 minutes

from $240 / night

(7) Excellent 

8

Boston Vacation apartment rental

Massachusetts / Boston

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 2 mi
  • Car not necessary
  • Air conditioning
Comfy 1 bedroom apartment in original neighborhood house in South Boston. Walk to downtown or Seaport. Bus transportation on the corner. Subway Red Line, Broadway Station, just down the street. Available this spring just in time for the Marathon. Bookings begin middle o …see more

from $100 / night

$700 / week

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from $100 / night

(3) Very Good 

35

Vacation apartment rental

Massachusetts / Boston

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child friendly
  • Air conditioning
Offering the best of old-world Boston and the newest 21-century conveniences, this charming Garrison Street two-bedroom might take you back in time. But the modern interior, featuring a full kitchen and fast WiFi, will bring you right back to today. The spacious layout …see more

from $128 / night

$896 / week

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from $128 / night

(1) Very Good 

30

Home rental in Boston

Massachusetts / Boston

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
Enjoy a top-notch location in downtown Boston at this modern condo. With shops, restaurants, and historic sights all around, plus updated amenities, a great balcony, and a community pool, you'll have everything you need. Located on the 30th floor of the Longfellow Pla …see more

from $49 / night

$343 / week

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Responds fast!
avg. 3 hours 2 minutes

from $49 / night

(2) Excellent 

25

Home rental in Boston

Massachusetts / Boston

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
Wake up in the heart of the South End at this one-bedroom Boston condo, a modern and comfortable escape with an upscale interior, a piano, and a wonderfully walkable location. This spacious condo sits on the fifth floor of a new building, right on the edge of Blackston …see more

from $49 / night

$343 / week

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avg. 3 hours 2 minutes

from $49 / night

31

Vacation apartment in Boston

Massachusetts / Boston

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
Experience the vibrant, contemporary style of South Boston at this two-bedroom condo, where you'll enjoy building amenities that include a gym, a game room, and a grilling patio, as well as wonderful access to the Seaport District, the T Red Line, and Logan Internationa …see more

from $72 / night

$504 / week

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Responds fast!
avg. 3 hours 2 minutes

from $72 / night

27

Vacation home in Boston

Massachusetts / Boston

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
Stay in this convenient condo in the heart of downtown Boston - complete with updated amenities, plenty of space, and access to a shared pool. Plus, you'll have a private balcony and beautiful city views for the ultimate urban retreat. Located in the West End area of …see more

from $75 / night

$525 / week

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avg. 3 hours 2 minutes

from $75 / night

(4) Very Good 

35

Vacation apartment accommodation

Massachusetts / Boston

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child friendly
  • Air conditioning
Offering the best of old-world Boston and the newest 21-century conveniences, this charming Garrison Street two-bedroom might take you back in time. But the modern interior, featuring a full kitchen and fast WiFi, will bring you right back to today. The spacious layout …see more

from $128 / night

$896 / week

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from $128 / night

(1) Excellent 

13

Vacation apartment in Boston

Massachusetts / Boston

1 3 4 nights min

  • 1 bedroom
  • sleeps 3
  • 4 nights min
  • Suitable for children age 5+
  • Car not necessary
  • Air conditioning
Bright, sunny, top floor 1 bedroom located on the most beautiful street in Boston's Back Bay. If you are looking for a quite, bright, homey place you will love this one bedroom apartment. Located on the top floor (4th) of a walk up, in a traditional brownstone buildin …see more

from $200 / night

$1,200 / week

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from $200 / night

(2) Excellent 

8

Vacation condo in Boston

Massachusetts / Boston

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Air conditioning
Ideal location in the South Boston neighborhood, easily accessible by public transportation. Only 10 minute cab ride to/from Logan Airport. Only 10 minute walk to Convention Center!! Short walk to Downtown/Financial District, Fort Point, Seaport District and other area …see more

from $300 / night

$2,000 / week

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Responds fast!
avg. 52 minutes

from $300 / night

32

Vacation apartment rental

Massachusetts / Boston

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child friendly
This lovely apartment features hardwood floors, fully equipped kitchen and a spacious bedroom. Located in Theater District, just steps to Boston Common and the Back Bay. This apartment features an open space living area, a spacious kitchen, hardwood floors, walking dis …see more

from $150 / night

$1,050 / week

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from $150 / night

(1) Excellent 

17

Vacation apartment in Boston

Massachusetts / Boston

1 2 30 nights min

  • 1 bedroom
  • sleeps 2
  • 30 nights min
1 Private room, shared kitchen & bathroom with other student/professional. Less than 3 mins walk to Red line train, food, market shops near by, 15 mins train ride to Downtown Boston, 20 min to MGH, 30 min to Longwood hospital Beth Israel, Downtown Financial District. …see more

from $30 / night

$210 / week

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Responds fast!
avg. 3 hours 37 minutes

from $30 / night

(22) Excellent 

Certificate of Excellence

30

Apartment rental in Boston

Massachusetts / Boston

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Brand new luxury apt square footage is 1350 over looking the Boston Harbor. Spectacular views of the skylines of Boston. Watch the boats go by or relax on your oversized private deck. Beautiful white table and four adirondack chairs sits on the deck. There is also a g …see more

Certificate of Excellence

from $300 / night

$2,100 / week

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Responds fast!
avg. 1 hour 38 minutes

from $300 / night

9

Vacation condo in Boston

Massachusetts / Boston

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Air conditioning
  • Pet friendly
  • Private garden
Located in the Sumner Hill area of Jamaica Plain. Close to Centre Street shops and restaurants as well as pond and Arboretum. Walkable to public transportation - 6 minutes to South end or Back Bay. This is a comfortable living space with full kitchen for dining in. Yo …see more

from $200 / night

$1,250 / week

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Responds fast!
avg. 15 minutes

from $200 / night

9

Vacation condo in Boston

Massachusetts / Boston

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Car not necessary
  • Air conditioning
  • Pet friendly
Newly renovated two bedroom apartment available close to Seaport, two blocks from convention center and one subway stop to South Station. Open deck, short walk to grocery store and restaurants, very close to airport and few blocks from major subway line. Minutes to Down …see more

from $300 / night

$2,000 - $2,350 / week

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from $300 / night

(1) Excellent 

35

Vacation apartment rental

Massachusetts / Boston

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child friendly
  • Air conditioning
Offering the best of old-world Boston and the newest 21-century conveniences, this charming Garrison Street two-bedroom might take you back in time. But the modern interior, featuring a full kitchen and fast WiFi, will bring you right back to today. The spacious layout …see more

from $110 / night

$770 / week

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from $110 / night

(2) Excellent 

16

Vacation apartment in Boston

Massachusetts / Boston

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child friendly
Our condo/apartment is a 2 minute walk to great restaurants, convenience stores, the Blue Line airport T-subway station, only two stations away from downtown Boston. There is a Free shuttle bus between the Airport T-station and the airport terminals. You will not need a …see more

from $250 / night

$1,750 / week

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Responds fast!
avg. 2 hours 48 minutes

from $250 / night

21

Apartment rental in Boston

Massachusetts / Boston

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Air conditioning
Convenience and comfort all in one apartment. Stay at our newly listed 3 bedroom and 2 bathroom apartment in the heart of North End's Little Italy. Dine at famous restaurants like Neptune's Oyster, Pizzeria Regina, Giacomo's Restaurant, Mike's Pastry, and more. Be steps …see more

from $119 / night

$833 / week

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Responds fast!
avg. 2 hours 50 minutes

from $119 / night

(4) Excellent 

26

Vacation apartment in Boston

Massachusetts / Boston

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Ask about children
This perfectly situated 4 bedroom apartment & 2 full baths was just completely renovated in 2014. Each bedroom features queen size beds. It has brand new full kitchen with granite countertops and new cabinets. Open living room with decorative fireplace. Hardwood floor t …see more

from $375 / night

$2,600 / week

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from $375 / night

(3) Excellent 

22

Vacation apartment in Boston

Massachusetts / Boston

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Beautifully renovated & right in the heart of the city! Spread out in 1,000 sq. ft. Designed to feel like a 5 star luxury hotel with all the comforts of home. 4K TV, Netflix, wifi. Exposed brick. Hardwood floors & new recessed LED lights throughout. Bedroom 1 has a king …see more

from $299 / night

$2,300 / week

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Responds fast!
avg. 1 hour 2 minutes

from $299 / night

13

Vacation apartment in Boston

Massachusetts / Boston

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Air conditioning
Tucked into a private courtyard in Boston's amazing North End, experience what it's like to live as a Bostonian. You are steps to the best historical sites, restaurants, market places and shopping in Boston. Old North Church is steps away, stroll down to the waterfr …see more

from $225 / night

$1,400 - $1,900 / week

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from $225 / night

(1) Excellent 

33

Apartment rental in Boston

Massachusetts / Boston

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Car not necessary
  • Air conditioning
Dressed exclusively for short term rentals 1-bedroom on the 1st floor -parlor with astonishing ceilings, new tall custom windows, new SS appliances and the best of Boston outside your door. Located ½ a block to Restaurant Row, where you’ll find some of the best dining …see more

from $199 / night

$1,399 - $1,749 / week

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from $199 / night

13

Vacation apartment rental

Massachusetts / Boston

1 1 30 nights min

  • 1 bedroom
  • sleeps 1
  • 30 nights min
  • Car not necessary
  • Private garden
1 Private room, shared kitchen & bathroom with other student/professional. Less than 3 mins walk to Red line train, food, market shops near by, 15 mins train ride to Downtown Boston, 20 min to MGH, 30 min to Longwood hospital Beth Israel, Downtown Financial District. …see more

from $50 / night

$350 / week

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Responds fast!
avg. 3 hours 37 minutes

from $50 / night

(13) Excellent 

59

Vacation apartment in Boston

Massachusetts / Boston

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
Comfortable, elegant, and romantic! Three-room luxury art suite with authentic European furnishings. In beautifully restored, award-winning historic townhouse located in Boston's oldest neighborhood of Charlestown! Lovely, walkable district near Freedom Trail, Bunker H …see more

from $226 / night

$1,500 / week

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Responds fast!
avg. 3 hours 0 minutes

from $226 / night

24

Vacation studio in Boston

Massachusetts / Boston

Studio 3 min stay varies

  • Studio
  • sleeps 3
  • min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
"One of Boston’s most picturesque areas, tony Beacon Hill has steep streets lined with Federal-style and Victorian brick row houses lit by antique lanterns. The gold-domed Massachusetts State House overlooks Boston Common, with its winter skating pond. Across Charles St …see more

from $146 / night

$1,022 / week

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Responds fast!
avg. 3 hours 55 minutes

from $146 / night

(1) Excellent 

12

Vacation apartment in Boston

Massachusetts / Boston

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Suitable for children age 5+
  • Car not necessary
  • Air conditioning
Brand new, bright beautiful, two bedroom in historic building steps to Faneuile Hall market place, little Italy in the North End, TD Garden and the Haymarket T stop. Easy access to airport and all the sights in Boston. Whether you want to spend a week-end in the city o …see more

from $280 / night

$1,500 - $2,100 / week

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from $280 / night

13

Vacation houseboat in Boston

Massachusetts / Boston

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Car not necessary
Experience Boston from the unique perspective of your own floating house! Nestled in a protected marina in Boston Harbor, our houseboat is fully equipped with all the comforts and amenities of home! Located in a very secure and gated marina, our houseboat is just minut …see more

from $300 / night

$2,100 - $2,450 / week

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from $300 / night

(2) Excellent 

39

Apartment rental in Boston

Massachusetts / Boston

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Child friendly
  • Air conditioning
This Brown Stone apartment is right in the heart of academic area of Boston Between Long Wood and Fen Way area. Two subway stations and bus terminal just a short stroll away. Street parking , two hour limit during the day and free at night except snow emergency and stre …see more

from $350 / night

$1,800 - $2,220 / week

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from $350 / night

11

Boston Vacation apartment rental

Massachusetts / Boston

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
Open layout two bedroom apartment in Boston's Little Italy makes for the ideal family getaway, business trip, or reunion of friends. With plenty of natural light, breathtaking views, and bright decor, you will be located among all the best that Boston has to offer from …see more

from $69 / night

$483 / week

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Responds fast!
avg. 2 hours 50 minutes

from $69 / night

28

Home rental in Boston

Massachusetts / Boston

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
Gaze at the Boston seaport skyline from this one-bedroom condo, an elegant urban home with a communal roof terrace, a gym inside the building, and a wonderful location close to the T Red and Silver Lines. This condo is located in the Signal Industries Building, a one- …see more

from $49 / night

$343 / week

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Responds fast!
avg. 3 hours 2 minutes

from $49 / night

(48) Very Good 

41

Vacation apartment rental

Massachusetts / Boston

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This upscale three-bedroom apartment is the ultimate Beantown abode for business travelers, vacationers, and seafood aficionados who want comfort and convenience. Featuring a fully-equipped kitchen, in-unit laundry, and public transportation pretty much on your doorstep …see more

from $146 / night

$1,022 / week

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from $146 / night

18

Vacation condo in Boston

Massachusetts / Boston

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
Our North End vacation home was designed to make us feel like we are staying in a 5 star luxury hotel... it will make you feel that way too. Located in Boston's historic North End and just steps away from the Waterfront, Rose Kennedy Greenway, Freedom Trail, Paul Rever …see more

from $250 / night

$1,650 / week

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Responds fast!
avg. 2 hours 26 minutes

from $250 / night