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Holiday Rentals in Boston, MA

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    Travellers to Boston are booking May dates now. Secure your holiday home today, and have the perfect trip.
    5 of 5 bubbles
    2 Reviews
    3 BedroomsSleeps 6Quick View
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    South End
    4.5 of 5 bubbles
    5 Reviews
    1 BedroomSleeps 2Quick View
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    Back Bay
    4 of 5 bubbles
    2 Reviews
    StudioSleeps 2Quick View
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    Jamaica Plain / Mission Hill
    3 BedroomsSleeps 4Quick View
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    About this property
    This beautiful sun filled, spacious apartment is located close to public transportation and the beautiful Arnold Arboretum, shopping and Jamaica Pond. You’ll love the location, the views and the new kitchen and bath. The three bedrooms are perfect for couples and business travelers.
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    Boston, Massachusetts 02130
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 4
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    South End
    4 of 5 bubbles
    1 Review
    1 BedroomSleeps 2Quick View
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    • Washer
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    • Porch
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    Pet friendly
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    Smoking allowed
    About this property
    The first in Boston for Vacation Rentals, since 1985. Member of the Greater Boston Convention Bureau since. These newly renovated studio apartments have a queen sized bed and full private bath. Queen bed Full private marble bathroom High top table and seating for dining or work Gas fireplace...
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    Boston, Massachusetts 02116
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Jamaica Plain / Mission Hill
    4.5 of 5 bubbles
    15 Reviews
    2 BedroomsSleeps 6Quick View
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    • Outdoor Dining Area
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    • Shared Garden
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    Pet friendly
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    About this property
    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 'Ladylike' by Christine Li...
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    Boston, Massachusetts 02130
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Beacon Hill
    5 of 5 bubbles
    1 Review
    StudioSleeps 2Quick View
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    About this property
    The Space Newly updated studio located next to State House and Boston Common. Great location. Studio has a full size bed. Full kitchen, including stove/oven, refrigerator etc. Amenities include television with cable, and wireless internet. Also has air conditioning and heat. Building has...
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    Boston, Massachusetts 02108
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    5 of 5 bubbles
    63 Reviews
    2 BedroomsSleeps 5Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    About this property
    Located in the heart of Seaport, 315 on A provides one-stop-shop living just steps away from Boston's best dining, nightlife, and entertainment. Boston's most environmentally-friendly community was designed with you in mind, boasting open kitchens, stainless-steel appliances, hardwood floors, and...
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    Boston, Massachusetts 02210
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Beacon Hill
    5 of 5 bubbles
    14 Reviews
    1 BedroomSleeps 3Quick View
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    About this property
    We've been renting high-quality furnished accommodations for over 8 years, exclusively in the Beacon Hill neighborhood. The "Luci Bella" apartment location is stellar, just 3 minutes walking distance to Boston Common, the Freedom Trail, an organic grocery store, three wine shops and many more...
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    Boston, Massachusetts 02114
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    About this property
    BEDROOMS: 2, BATHROOMS: 1, SLEEPS: 6 My place is close to Neptune Oyster, The Liberty, a Luxury Collection Hotel, Boston, Boston Public Market, Modern Pastry, and Bricco. You’ll love my place because of the people, the ambiance, the light, and the neighborhood. My place is good for couples, solo...
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    Boston, Massachusetts 02113
    Condo/Apartment - 6 Bedrooms, 1 Bathroom, Sleeps 6
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    Dorchester / Roxbury / Mattapan
    4 of 5 bubbles
    14 Reviews
    1 BedroomSleeps 4Quick View
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    About this property
    This 3rd floor one bedroom suite features a full sized, open kitchen and living room that looks out onto a great view of the city and neighborhood. This brand new unit has polished hardwood floors throughout the unit, central air, marble countertops and new stainless steel appliances. The bedroom...
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    Boston, Massachusetts 02118
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 BedroomSleeps 4Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore all of Boston with ease when you stay at this chic one-bedroom condo. In addition to the convenient location, you'll have access to a seasonal shared swimming pool and a private balcony with views of the city. Situated in the West End neighborhood, this condo is half a mile from Boston...
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    Boston, Massachusetts 02114
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South End
    1 BedroomSleeps 4Quick View
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    About this property
    102 Chandler St is a quiet street located in the Heart of the South End/Back Bay. WalkingWest Elm furniture through out this unit with upscale beddings and mattresses.Hardwood floors throughout, freshly-painted 1BD/1BA apartment offers a high ceiling living room, Full Kitchen, Nespresso machine and...
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    Boston, Massachusetts 02116
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Charlestown
    5 of 5 bubbles
    16 Reviews
    1 BedroomSleeps 2Quick View
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    • DVD Player
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    • Shared Garden
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Romantic, comfortable, and elegant! 3-room luxury art suite with authentic Moroccan furnishings, in beautifully-renovated & historic Boston townhouse close to the Freedom Trail, downtown, Boston Garden. King feather bed with canopy tent. Elegant living room with fireplace. Marble bath with...
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    Boston, Massachusetts 02129
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    South End
    5 of 5 bubbles
    1 Review
    1 BedroomSleeps 4Quick View
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    • Balcony
    • Outdoor Dining Area
    • Terrace
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The first in Boston for Vacation Rentals, since 1985. Member of the Greater Boston Convention Bureau since. One bedroom apartment with modern amenities. There are three of these apartments, all very much alike with variations in furnishings. Private bedroom with queen bed Living room with sofa bed...
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    Boston, Massachusetts 02116
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4.5 of 5 bubbles
    56 Reviews
    2 BedroomsSleeps 5Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    While we decorate each condo similarly, minor differences between condos may not be reflected in the photographs. Call 24/7 or visit the Stay Alfred website to book or to learn more about all of our Boston Vacation Rentals! Located in the West End, Longfellow by Stay Alfred puts you in the midst of...
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    Boston, Massachusetts 02114
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    South Boston
    2 BedroomsSleeps 5Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether you're visiting Washington, D.C. for business or for pleasure, Stay Alfred's vacation rentals at Andover House have all the amenities and comforts that you need for a stress-free stay in our nation's capital. Work on business matters in the community conference room, or go work up a sweat...
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    Boston, Massachusetts 20005
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4.5 of 5 bubbles
    58 Reviews
    2 BedroomsSleeps 5Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the West End, the gorgeous Avenir by Stay Alfred offers Boston's premier vacation accommodations. Part of the recently revitalized Bulfinch Triangle Historic District, Avenir features gourmet kitchens and upscale design elements like high ceilings and cherry plank wood flooring....
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    Boston, Massachusetts 02114
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Beacon Hill
    4.5 of 5 bubbles
    6 Reviews
    StudioSleeps 2Quick View
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    About this property
    This 4th floor (elevator access) studio suite features a custom designed and built murphy bed that provides the ultimate in comfort and flexibility for a studio unit. The unit is front facing with incredible views of Charles Street and Beacon Hill. This brand new unit has hardwood floors...
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    Boston, Massachusetts 02114
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Back Bay
    4 of 5 bubbles
    22 Reviews
    3 BedroomsSleeps 7Quick View
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    About this property
    This floor through unit is on the third level of the property, 2 flights up from the entrance of the building, allowing additional privacy and quiet to its guests. The kitchen is fully-equipped with appliances, including oven, refrigerator, and microwave, as well as quality pots, pans and cooking...
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    Boston, Massachusetts 02116
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    South End
    5 of 5 bubbles
    8 Reviews
    1 BedroomSleeps 3Quick View
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    About this property
    One bedroom apt in elegantly renovated historic brownstone on one of the neighborhoods finest streets. Walk to historic and cultural sites Steps from fine dining, shops and cafes High ceilings and rich architectural detail New fully equipped granite kitchen Huge marble bathroom Very bright and...
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    Boston, Massachusetts 02118
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    5 of 5 bubbles
    1 Review
    1 BedroomSleeps 4Quick View
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    This 4th floor one bedroom suite features a full sized, open kitchen and living room that looks out onto a great view of the city and neighborhood. This brand new unit has polished hardwood floors throughout the unit, granite countertops and new stainless steel appliances. The bedroom features a...
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    Boston, Massachusetts 02115
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 BedroomsSleeps 6Quick View
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    • Central Heating
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    Wonderful 2 bedroom apartment, very sunny, w/large windows and a high ceiling. Sleeps 4-6 guests. One bedroom has a loft bed w/twin on bottom and full bed on top. 2nd BR has a queen size bed. Newly renovated kitchen and bathroom with shower/tub combo. There is one sofa that can be used for...
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    Boston, Massachusetts 02109
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Beacon Hill
    StudioSleeps 2Quick View
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    About this property
    Our home is located next to the historic State House and the much-loved Boston Commons. Our condo features high ceilings, Update laminate hardwood floors, and an open kitchen with granite counter top, cabinet and stainless steel appliances. Enjoy the modern feel of a newly furnished condo!...
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    Boston, Massachusetts 02108
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Back Bay
    1 BedroomSleeps 4Quick View
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    About this property
    Gloucester St is a quite street located in the Heart of the Back Bay. we have usedWest Elm furniture to furnish this unit with upscale beddings and mattresses.Hardwood floors throughout, freshly-painted 1BD/1BA apartment offers a spacious living room with a decorative fireplace and north-facing...
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    Boston, Massachusetts 02115
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Back Bay
    4 of 5 bubbles
    22 Reviews
    2 BedroomsSleeps 5Quick View
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    This upper level two bedroom unit is characterized by great light and has a private rooftop deck with outdoor seating for 6, offering privacy and a view of the city. Polished hardwood floors run throughout the unit. The bedrooms feature queen mattresses, ceiling fan, nightstand, reading lamp and...
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    Boston, Massachusetts 02116
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    South End
    StudioSleeps 3Quick 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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    Boston, Massachusetts 02118
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    Jamaica Plain / Mission Hill
    2 BedroomsSleeps 5Quick View
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    Modern apartment in a JP 2 family. To read reviews and if you do not see your dates here please see my other listing # Enjoy our extensive collection of fresh local art. This is not your standard run of the mill rental. Collection will occasionally rotate. Currently showing 'Ladylike' by...
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    Boston, Massachusetts 02130
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Back Bay
    4.5 of 5 bubbles
    4 Reviews
    2 BedroomsSleeps 6Quick View
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    The first in Boston for Vacation Rentals, since 1985. Member of the Greater Boston Convention Bureau since. Located in the heart of Boston's prestigious Back Bay, this is a lovely architecturally renovated historic Victorian brownstone building. You will have all of the modern conveniences of...
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    Boston, Massachusetts 02116
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    South End
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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 historic...
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    Boston, Massachusetts 02118
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    Beacon Hill
    4.5 of 5 bubbles
    20 Reviews
    3 BedroomsSleeps 6Quick View
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    About this property
    This newly renovated garden/parlor level duplex features 3 bedrooms, all with queen-sized beds, 1.5 bathrooms, modern eat-in kitchen and full-sized living room. This unit has in-unit laundry. The unit has a set of interior stairs, but both levels of the unit can be accessed by the common elevator....
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    Boston, Massachusetts 02114
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Back Bay
    1 BedroomSleeps 4Quick View
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    About this property
    Experience Boston in elegance and style at this one-bedroom condo, a historic property with a communal roof deck, gorgeous city views, and a perfectly walkable location close to restaurants, shopping, and more. This light-filled condo is located on the fifth floor of The Carlyle, a building that...
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    Boston, Massachusetts 02215
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Allston / Brighton
    5 of 5 bubbles
    8 Reviews
    1 BedroomSleeps 4Quick View
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    • Terrace
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    About this property
    A sunlit and wonderfully located apartment on Radcliffe road. - 660 sq f in Allston/Brookline area. 25 min from downtown Boston on subway (Green line B) 15 min walk to Coolidge corner 15 min to Harvard Sq.Cambridge by bus 66. Easy access to Boston University, Boston College, Harvard University and...
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    Boston, Massachusetts 02134
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Back Bay
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    This one bedroom apartment in an elevator building offers a fully stocked kitchen, cable TV, wifi, recently updated kitchen with stainless steel appliances. The living room also offers a fold down couch for additional guests. This prime location is walking distance to Fenway Park or the Back Bay...
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    Boston, Massachusetts 02215
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    South Boston
    1 BedroomSleeps 4Quick View
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    About this property
    Relax and feel at home in our privately-owned residences featuring spectacular views of the luxurious Seaport District and Boston Harbor. These one bedroom suites include brand new kitchens with stainless steel appliances. Step into the living room and enjoy stylish furniture, hardwood floors, and...
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    Boston, Massachusetts 02210
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 BedroomsSleeps 6Quick View
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    Light-filled, 4th floor apartment with hardwood floors and open layout kitchen. Nice view of Boston's sky line at night. can accommodate 4 guests. night view of the Boston skyline, Two small bedrooms with queen size beds , one in each bedroom. a full size sofa bed in The living room that can be...
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    Boston, Massachusetts 02113
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4.5 of 5 bubbles
    51 Reviews
    2 BedroomsSleeps 8Quick View
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    A rare find! Brand new three bedroom, three bathroom duplex. This unique duplex is beautifully decorated, with a spacious living-room that has a full size sleeper sofa connected to a state-of-the-art kitchen with granite top and stainless steel appliances . The upper floor has a living room with...
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    Boston, Massachusetts 02113
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 of 5 bubbles
    6 Reviews
    1 BedroomSleeps 4Quick View
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    Situated 1,300 feet from Boston University in Boston, this air-conditioned apartment features free WiFi. The apartment is 1,650 feet from Fenway Park. The kitchen is fitted with a dishwasher. A flat-screen TV and DVD player are available. Other facilities at Evolve Fenway Diamond include a fitness...
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    Location Information
    Boston, Massachusetts 02215
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4.5 of 5 bubbles
    41 Reviews
    3 BedroomsSleeps 7Quick View
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    • Internet Access
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    • Patio
    • Private Indoor Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience downtown Boston's finest in location and amenities! The stunning 660 Washington building features 9 ft. ceilings, over sized windows, and upscale kitchens in every condo. The property also boasts a plethora of on-site amenities such as a heated indoor pool, state-of-the-art business and...
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    Location Information
    Boston, Massachusetts 02111
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    South Boston
    2 BedroomsSleeps 8Quick View
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    • Satellite TV
    • Private Garden
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    Pet friendly
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    Come enjoy our newly renovated space! We have a single family home that's two bedrooms two baths, 900sf. There are 3 levels. First level is a modern living room with gleaming large format white tiles. Also on the first floor is the kitchen that has a white marble backsplash wall and skylight with...
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    Location Information
    Boston, Massachusetts 02127
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Boston
    3 BedroomsSleeps 10Quick View
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    • Wi-Fi
    • Washer
    • Grill
    • Satellite TV
    • Air Conditioning
    • Terrace
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home has updated hardwood flooring, appliances, lighting and more. The main level offers open-concept living and kitchen area with a 1/2 bath and full laundry off the kitchen. The chef's kitchen includes granite counters, stainless steel appliances (refrigerator that includes filtered water...
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    Location Information
    Boston, Massachusetts 02127
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Charlestown
    2 BedroomsSleeps 8Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Balcony
    • Satellite TV
    • Secure Parking
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a large modern, clean 2 bedrooms / 3 beds + bathroom + full kitchen Bus stops, train stations and downtown are all walking distance. Food store across the street, Whole Foods, coffee shops, bars, restaurants, gym and pool all nearby. Historic sites are all walking distance as well: Navy...
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    Location Information
    Boston, Massachusetts 02129
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Beacon Hill
    3 BedroomsSleeps 7Quick View
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    BEDROOMS: 3, BATHROOMS: 2, SLEEPS: 7 My place is on Charles Street in the heart of Beacon Hill. One of the nicest streets in Boston - John Kerry lives on the same block. You’ll love my place because of the people, the neighborhood, and the ambiance. My place is good for couples, solo adventurers,...
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    Location Information
    Boston, Massachusetts 02114
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Back Bay
    StudioSleeps 1Quick View
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    This spacious studio is located in the heart of Back Bay, minutes from Cambridge or the North End. It is ideally located very close to the start of the Freedom Trail or head over to the Public Garden. There are public transportation stops all around to take you wherever you may need to go. The...
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    Location Information
    Boston, Massachusetts 02115
    Holiday Rental House - Sleeps 1
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    Back Bay
    4.5 of 5 bubbles
    23 Reviews
    1 BedroomSleeps 4Quick View
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    This 2nd floor one bedroom suite is one of our two premier units. It features a full sized, open kitchen and living room that looks out onto a great view of the city and neighborhood. The high-end finishes, architectural design, and furniture really distinguish this unit from the other units in the...
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    Location Information
    Boston, Massachusetts 02115
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beacon Hill
    5 of 5 bubbles
    1 Review
    1 BedroomSleeps 2Quick View
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    About this property
    Classic and Comfortable furnished apartment in Boston's Beacon Hill neigbhorhood. Located next to Mass General Hospital and steps to downtown, financial district and the north end/waterfront. Renovated kitchen featuring; granite breakfast bar maple cabinets and stainless steel appliances. Sunny...
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    Location Information
    Boston, Massachusetts 02114
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    North End
    4.5 of 5 bubbles
    47 Reviews
    2 BedroomsSleeps 6Quick View
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    *** Celebrating 25 Years in Business as Boston's Original B&B Afloat *** If you are looking for an absolutely unique and romantic getaway experience to celebrate a birthday, anniversary, engagement, or wedding, the Golden Slipper awaits. It is an ideal romantic getaway for two, but also a fun...
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    Location Information
    Boston, Massachusetts 02110
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Back Bay
    1 BedroomSleeps 4Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gloucester St is a quite street located in the Heart of the Back Bay. We have usedWest Elm furniture to furnish this unit with upscale beddings and mattresses.Hardwood floors throughout, freshly-painted 1BD/1BA apartment offers a spacious living room with a decorative fireplace and north-facing...
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    Location Information
    Boston, Massachusetts 02115
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South Boston
    4.5 of 5 bubbles
    2 Reviews
    1 BedroomSleeps 4Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Relax and feel at home in our privately owned residences featuring spectacular views of the luxurious Seaport District and Boston Harbor. These one bedroom suites include brand new kitchens with stainless steel appliances. Step into the living room and enjoy stylish furniture, hardwood floors, and...
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    Location Information
    Boston, Massachusetts 02210
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Charlestown
    4 of 5 bubbles
    2 Reviews
    2 BedroomsSleeps 4Quick View
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    This furnished two bed, second floor apartment is situated on a quiet, one way street allows flowing access to a private outside garden patio area behind the building. Both bedrooms have a queen size bed with linens, pillows and blankets included. The bright kitchen is fully-equipped with...
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    Location Information
    Boston, Massachusetts 02129
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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