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Cheap Boston Holiday Homes

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    Travellers to Boston are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    155 Matching Rentals in BostonView all 620 rentals
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    Ideal Location Private Room with Airbed!1 / 16
    (1)Excellent
    Dorchester / Roxbury / Mattapan
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Dorchester / Roxbury / Mattapan
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Dorchester / Roxbury / Mattapan
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    About this property
    This 'Private Room' comes with a built-in electric pump High-Rise Airbed, a computer desk & chair, closet and secure door lock in a 3 bedroom apartment, sharing all common areas like the bathroom and kitchen with 2 guests. Utilities (Gas, hot water, electricity) and Wifi are all included....
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    Boston, Massachusetts 02121
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 1
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    South End
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    About this property
    At this Sonder, you'll love the fully-equipped kitchen, chic decor, and family-style living space with double beds in one room. Located in the South End, known for its wonderful restaurants and neighborhood charm, you're close to the Massachusetts Avenue T Station. Every booking is instantly...
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    Boston, Massachusetts 02118
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    South End
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    At this Sonder, you'll love the modern decor, fully-equipped kitchen, and large windows providing plenty of natural light. Located in the South End, known for its wonderful restaurants and neighborhood charm, you're close to the Massachusetts Avenue T Station. Every booking is instantly confirmed....
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    Boston, Massachusetts 02118
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Dorchester / Roxbury / Mattapan
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Central Heating
    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    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. No Pets! This is a quiet,...
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    Boston, Massachusetts 02124
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 1
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    Allston / Brighton
    5 Bedrooms, 2 Bathrooms, Sleeps 1 Quick View
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    Pet friendly
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    About this property
    One room for one person for rent in a house with 2 floors, 2.5 baths but only 1.5 shared bathrooms provided for guests. Others: International grad students mixed gender mostly males, long term or short term, all carefully screened by owner who resides in the same house. Smoking/smokers prohibited....
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    Boston, Massachusetts 02134
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 1
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    Beacon Hill
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This spacious studio with sleeping alcove in Beacon Hill will have you considering a permanent move to Boston. Perfect for couples and solo travelers, this trendy apartment will leaving you feeling right at home. The Space: This luxury apartment boasts more than your average studio as the sleeping...
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    Boston, Massachusetts 02114
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    West Roxbury / Hyde Park / Roslindale
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Available from Feb 1 until April 30 (possibly longer). This beautifully furnished artist's home is bright, warm and sunny. The street is very quiet with ample street and driveway parking. Hardwood floors, new windows, all the kitchen appliances, stove, fridge, dishwasher, microwave, expresso...
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    Boston, Massachusetts 02155
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 2
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    Adorable vintage condo in South End w/ updated finishes & great location!1 / 28
    (2)Excellent
    South End
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    Reviewed 24 September 2017
    We thoroughly enjoyed the perfect studio, it was immaculate, tastefully decorated and very comfortable. All the necessary amenities were provided. The studio was close to the...
    Reviewed 25 July 2017
    This is a great place to stay! The building is charming, safe, and has a brilliant location. The kitchen has everything you need and the washer and dryer (shared) are located...
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    About this property
    Experience the history of the beautiful city of Boston when you stay at this stunning vintage condo. Conveniently located in South End, you'll have updated finishes, great amenities, and a top-notch location in the heart of one of downtown's best neighborhoods. This condo is located in the...
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    Location Information
    Boston, Massachusetts 02118
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    South Boston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Couples and small families alike will enjoy this sleek home on Boston's south side. All the comforts you need to relax are present and accounted for, with a vibrant neighborhood only a few moments away! The condo features a central location only a few blocks from the main drag on West Broadway....
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    Boston, Massachusetts 02127
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Back Bay
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Balcony
    • Terrace
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    Pet friendly
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    Smoking allowed
    About this property
    Just west of Boston Common and Boston Public Garden, Stay Alfred on Garrison Street offers the best of old and new. The building's historic brick facade and wrought-iron details belie the interior's modernity – each Boston vacation rental is flush with every modern convenience, from a full kitchen...
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    Boston, Massachusetts 02116
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This unique and quintessential apartment, perfect for couples and solo travelers, has more to offer than your average studio. Situated in the heart of the North End, your home away from home will be just steps from the Freedom Trail, Paul Revere's House, and the absolute best restaurants in...
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    Location Information
    Boston, Massachusetts 02113
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Back Bay
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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 and stylish decor make this...
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    Location Information
    Boston, Massachusetts 02116
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    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 International Airport. This condo is...
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    Location Information
    Boston, Massachusetts 02127
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    South End
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    This lovely South End condo has historic charm and a great, central location! This condo is nestled among the scenic brownstones in South End Boston. Enjoy walks in the heart of one of Boston's most historic neighborhoods, check out the restaurants and shops within a few miles, or hop on public...
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    Location Information
    Boston, Massachusetts 02118
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    South Boston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience one of the most storied neighborhoods in Boston at this one-bedroom condo, an elegant South Boston retreat with a shared gym, game room, and terrace, as well as fantastic access to the T Red Line and the Seaport District. This condo is part of the West Square Apartments, an upscale...
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    Location Information
    Boston, Massachusetts 02127
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South Boston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Grill
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the best of Boston from the comfort of this beautiful, modern condo! The interior is full of well-designed details, from the wonderful natural light to the kitchen backsplash. This rental's building offers great amenities like a fitness room, ping pong, and a shared patio and grill area....
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    Location Information
    Boston, Massachusetts 02127
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Jamaica Plain / Mission Hill
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    BEGINNING JANUARY 1, 2019, ALL UNITS WILL HAVE A 28 DAY MINIMUM STAY DUE TO CITY OF BOSTON ORDINANCE ALLOWING SHORT-TERM RESIDENTIAL RENTALS IN THE CITY OF BOSTON All New for Fall 2017! Wonderfully built brand new 1 bed / 1 bath apartment in Jamaica Plain with patio! Minutes walk to gorgeous...
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    Location Information
    Boston, Massachusetts 02130
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideal for families looking to explore the urban jewel of Massachusetts, this Boston condo has everything you need for your next vacation. A great location, free WiFi, and community amenities like a Ping-Pong table and fitness room ensure your next getaway to Beantown will be your most memorable...
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    Location Information
    Boston, Massachusetts 02127
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    TheLedders1 -Fullbed/2 Bth near city/T/Freeparking1 / 26
    (1)Excellent
    Dorchester / Roxbury / Mattapan
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Private Garden
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    Reviewed 9 February 2018
    The location is in heart of dorchester area, 6 mins to South Bay Center which is perfect with some eatery, shopping and movies, 8-12 mins walk to Savin Hill Station towards...
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    About this property
    Your next room. Beautifully renovated House located on the 3rd fl with 5 private bedrooms. This room has a full size bed in a private room . Patio/backyard for you to relax, cook and enjoy. 2 bathroom and a full kitchen with coffee maker, toaster, blender and all cookware. We provide free linens,...
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    Boston, Massachusetts 02122
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Dorchester / Roxbury / Mattapan
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Garden
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    About this property
    Your next private room. Renovated House located on the 3rd fl with 5 private bedrooms. Room#2 is a King size bed and full size sofa bed .Patio/backyard for you to relax, cook and enjoy. 2 bathroom and a full kitchen with coffee maker, toaster, blender and all cookware. We provide free linens,...
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    Location Information
    Boston, Massachusetts 02122
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    Jamaica Plain / Mission Hill
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    BEGINNING JANUARY 1, 2019, ALL UNITS WILL HAVE A 28 DAY MINIMUM STAY DUE TO CITY OF BOSTON ORDINANCE ALLOWING SHORT-TERM RESIDENTIAL RENTALS IN THE CITY OF BOSTON Wonderfully built brand new 820sq foot 1 bedroom/1 bath apartment in Jamaica Plain with patio! Minutes walk to gorgeous Jamaica Pond...
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    Location Information
    Boston, Massachusetts 02130
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GetDescriptionsPlainText: Error - The description is blank Additional amenities: Foosball
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    Location Information
    Boston, Massachusetts 33837
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    At this Sonder, you'll love the spacious layout, white and gray marble designs, and fully-equipped kitchen. Located in the Financial District, steps away from the waterfront. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with crisp...
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    Boston, Massachusetts 02109
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    At this Sonder, you'll love the contemporary decor, bright natural lighting, and fully-equipped kitchen. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is...
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    Boston, Massachusetts 02110
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This posh studio features a modern bathroom, contemporary furnishings, and a fully-equipped kitchen. Located in Downtown Crossing, just steps from the T and minutes to Boston Common. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with...
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    Boston, Massachusetts 02110
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    At this Sonder, you'll love the stylish decor, beautiful natural lighting, and fully-equipped kitchen. Located in the heart of Boston you're close to the Common, Theatre District, and more! Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is...
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    Boston, Massachusetts 02110
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Back Bay
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    At this Sonder, you'll love the huge windows, fully-equipped kitchen, and amazing location. This apartment is in Back Bay known for its fashionable shops and close to Hynes Convention Center T Station. Every booking is instantly confirmed. Every call or message is answered within minutes. Every...
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    Boston, Massachusetts 02115
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    At this Sonder, you'll love the open-concept living space, modern decor, and fully-equipped kitchen with ensuite laundry. Located in Downtown Crossing and in the heart of Boston's shopping district, just 1-2 blocks away from the Boston Common. Every booking is instantly confirmed. Every call or...
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    Location Information
    Boston, Massachusetts 02111
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    At this Sonder, you'll love the high ceilings, distinctive decor, and modern, fully-equipped kitchen. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped...
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    Boston, Massachusetts 02111
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    About this property
    This classic studio features a fully-equipped kitchen, a renovated bathroom, and lovely floors. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with...
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    Boston, Massachusetts 02110
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Back Bay
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    At this Sonder, you'll love the sleek hardwood floors, open-concept living area, and beautiful architectural details. Located in Back Bay known for its fashionable shops, river-side walkways, and excellent restaurants. This homey studio apartment is located in the heart of Boston's Back Bay area,...
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    Location Information
    Boston, Massachusetts 02116
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Back Bay
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    At this Sonder, you'll love the sleek hardwood floors, modern kitchen, and large bright windows. Located in Back Bay, a short walk to fashionable shops, river-side walkways, and excellent restaurants. This homey apartment is located in the heart of Boston's Back Bay area, fully equipped with...
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    Boston, Massachusetts 02116
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    About this property
    This lively studio boasts sleek hardwood floors, fully-equipped kitchen, and a queen-size bed. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with...
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    Boston, Massachusetts 02110
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This modern studio welcomes you with contemporary furnishings, a fully-equipped kitchen, and incredible hardwood floors. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes....
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    Boston, Massachusetts 02110
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This studio boasts a renovated bathroom, chic furnishings, and a fully-equipped kitchen. Located in Downtown Crossing, just steps from the T and minutes to Boston Common. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with crisp...
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    Location Information
    Boston, Massachusetts 02110
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    About this property
    At this Sonder, you'll love the expansive windows, sleek decor, and stunning fully-equipped kitchen. Located in Downtown Crossing, known for its assortment of delicious restaurants and relaxed cafes. Every booking is instantly confirmed. Every call or message is answered within minutes. Every...
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    Boston, Massachusetts 02110
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    About this property
    At this Sonder, you'll love the industrial-style high ceilings, light-filled living area, and central location. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is...
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    Boston, Massachusetts 02111
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Back Bay
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    About this property
    At this Sonder, you'll love the vintage-inspired decor, spacious living area, and classic hardwood floors. Located in Back Bay, a short walk to fashionable shops, river-side walkways, and excellent restaurants. This homey apartment is located in the heart of Boston's Back Bay area, fully equipped...
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    Location Information
    Boston, Massachusetts 02116
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    About this property
    This chic studio is complete with a renovated bathroom, a fully-equipped kitchen, and sleek furnishings. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is...
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    Location Information
    Boston, Massachusetts 02110
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the spacious living area, rich decor, and modern, sleek kitchen. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with...
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    Location Information
    Boston, Massachusetts 02111
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Charming Studio in Downtown Crossing by Sonder1 / 15
    (1)Terrible
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Smoking allowed
    About this property
    At this Sonder, you'll love the fully-equipped kitchen, cozy furniture, and modern decor. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with crisp...
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    Location Information
    Boston, Massachusetts 02116
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This simple studio boasts a lovely skylight, a fully-equipped kitchen, and sleek furniture. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with crisp...
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    Boston, Massachusetts 02110
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Lovely Loft in Downtown Crossing by Sonder1 / 20
    (1)Excellent
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    Reviewed 1 week ago
    This was a great space! It was so close to the sights of downtown Boston (steps away from the Freedom Trail) and very easy to access the T. Would stay here again in a heartbeat!
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    About this property
    At this Sonder, you'll love the architectural layout, chic decor, and fully-equipped, modern kitchen. Located in Downtown Crossing and in the heart of Boston's shopping district, just 1-2 blocks away from the Boston Common. Every booking is instantly confirmed. Every call or message is answered...
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    Location Information
    Boston, Massachusetts 02111
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the colorful decor, fully-equipped kitchen, and sleek hardwood floors. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped...
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    Location Information
    Boston, Massachusetts 02110
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the colorful decor, large windows with tons of natural light, and modern kitchen. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is...
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    Location Information
    Boston, Massachusetts 02116
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the open-concept living space, chic decor, and beautiful windows with natural light. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home...
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    Location Information
    Boston, Massachusetts 02116
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    This hip apartment boasts contemporary furnishings, a sleek kitchen, and a spacious bedroom. Located in Downtown Crossing, right by all the action in Boston's shopping district. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with...
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    Location Information
    Boston, Massachusetts 02110
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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