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Winchester Vacation Rentals

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    Don't let other travellers get your favourite Winchester area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 25 Rentals in Winchester
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    Nice room in a quiet New England town1 / 4
    (1)Excellent
    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    The following rentals are within 10 kilometres of Winchester.
    artistic, quiet, beautiful 2-room suite.1 / 16
    (4)Excellent
    Burlington
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    HUGE POOL HOUSE 4 BedRooms 2.5 Bathrooms ,3 Parking spots & a POOL!1 / 24
    (2)Excellent
    Arlington
    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 14, 2017
    The house was very clean, the beds were comfortable. The kitchen was well equipped. The location is perfect, very close to stores and restaurants. Otto, the owner, was great! He...
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    About this property
    Welcome! This is a Big and renovated house, we have 4 Beds/2.5 Bath, spacious and well equiped kitchen, comfortable living room, work space, BBQ area with POOL, and we also provide 3 private parking spots. Our house is located in a quite and safe neighboorhood, bus stop is just 2 blocks from the...
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    Arlington, Massachusetts 02476
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
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    Tufts-Area Large 2BD Apartment1 / 8
    (1)Average
    Medford
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Washer
    • Parking
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely 2BD unit right next to Tufts University. The apartment itself is very spacious and includes 2 bedrooms, a living room, a bathroom, and a full kitchen. It is a residential neighborhood and absolutely perfect for families or younger folks who want easy access to Tufts or the happenings in...
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    Medford, Massachusetts 02155
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Malden
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Grill
    • Hot Tub
    • Housekeeping Included
    • Wi-Fi
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is a three bedroom with central air and heating in a quiet neighborhood just ten minutes away from Boston and minutes away from public transportion. There is a hiking trail directly behind the property. The property also has free Wifi, Cable TV, Telephone and a Washer and Dryer for your...
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    Malden, Massachusetts 02148
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Somerville
    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
    The room has a private entrance and its own bathroom. Perfect for visiting couples, solo adventurers, and business travelers. Its mins from Assembly Sq and 15 min from Logan. Only 10 min walk to Sullivan Square on the Orange Line. Free Wifi. The Bus Stop runs direct to Kendall/MIT, Harvard, Tufts,...
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    Somerville, Massachusetts 02145
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Medford
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bright, spacious & quiet studio for business & leisure travelers mins from Boston with access to I-93 & MA28. Well connected to trains, buses & free parking. Secluded BdRm, clean private bath, dining, entertainment space with private deck. We are consistently rated 5 stars by our guests and are...
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    Medford, Massachusetts 02155
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Charming 4 room apartment, minutes from Cambridge and Boston1 / 20
    (3)Excellent
    Arlington
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 8, 2018
    This lovely home was exactly what we needed in a beautiful little Arlington neighborhood, walking distance to several restaurants and a great park for kids. It was hot during...
    Reviewed July 22, 2018
    We stayed in this adorable and very clean Arlington apartment for 7 days. It’s on a quiet street just a few short blocks away from Massachusetts Ave and the Minuteman bike trail...
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    About this property
    An easy 20 minute drive from Logan Int'l Airport to our door. A two minute walk to the bus stop will take you directly to Harvard Square and to Alewife Station. If you're driving, we are a few minutes to Route 2 and all roads that loop in and around the city and beyond. Or bike the beautiful...
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    Arlington, Massachusetts 02474
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Clarendon Road1 / 20
    (4)Excellent
    Belmont
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Central Heating
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 30, 2018
    The home was just as described...very room clean and the host is friendly. ★ ★ ★ ★ ★ The home is well maintained with adequate space and easy access. The parking was simple...
    Reviewed October 26, 2016
    The location was perfect for our needs and near Cambridge, the Charles River, A Star Market. Our host Mont is very welcoming and because of all of the above we are back for year...
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    About this property
    This is for travelers interested in weekend, weekday, week-long rentals (and longer) of a room in my Belmont home (near the Cambridge and Watertown lines). I am offering this, Airbnb-style, such that I live at the house and you will be sharing it with me. It's fantastic for short-term stays to...
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    Location Information
    Belmont, Massachusetts 02478
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 bedroom Colonial in Lexington neighborhood1 / 13
    (2)Excellent
    Lexington
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Terrace
    • Balcony
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 3, 2017
    The owner of this house is very friendlyNice and clean!Great Place to visit !We love it! Deeply respect and appreciation!
    Reviewed January 1, 2017
    Our family of 4 felt warmly welcomed in this comfortable home over the holidays. Our hosts provided many personal touches for us and they went the extra mile to be sure we had...
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    About this property
    This center-entrance Colonial has a large living room with a fireplace, oak moldings, built-in bookcases, and a piano. The second floor has a master bedroom with a king-size bed and single sofabed, and two additional bedrooms, one with a full size bed (can sleep 2) with a lovely, hand-painted...
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    Lexington, Massachusetts 02421
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Room with double bed minutes from Harvard Square1 / 8
    (1)Average
    Arlington
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 10, 2016
    I had booked and paid for a room with a double bed, but I was given a room with a single bed. The proprietor was away, and the person in charge was obviously not in charge of...
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    About this property
    Nicely appointed room in home with double bed, keurig coffee maker, fridge, and microwave. Shared bathroom. Lovely outdoor living areas with grill and hammock! 1 minute walk to bus, 5 minute walk to restaurants. 10 minute drive to Harvard Square. A friendly kitty lives in the home. Quiet, safe...
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    Arlington, Massachusetts 02476
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Everett
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand New listing! Come stay in this beautiful and well appointed duplex home! Enjoy your stay in this modern well furnished home with two floors of living space. Just steps away from public transportation & very close with easy quick access to Boston, Cambridge, Salem, & surrounding cities &...
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    Everett, Massachusetts 02149
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Medford
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Terrace
    • DVD Player
    • Balcony
    • Parking
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    10 Minute drive to Boston or Cambridge. Short walk to public transportation and Tufts University. Single family home for rent, 3 Bedrooms, 3 Baths. Granite Counters, Stainless Appliances, Hardwood Floors throughout, Central A/C, Gas Fireplace. Washer & Dryer. Wireless Internet, 3 TVs, Keurig coffee...
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    Medford, Massachusetts 01876
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Somerville
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    • Cable/satellite TV
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Space Rent a room in a 5 bedroom, 2 bathroom apartment in Somerville. Washer/Drier in Basement. Common living room and kitchen. Close to Boston and Tufts, Harvard, and MIT via MBTA buses and T connections. Easy access to multiple bus routes. Only an easy 10-15 minute walk to the shops,...
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    Somerville, Massachusetts 02145
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Somerville
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Space Rent a room in a 3 bedroom, 1 bathroom apartment in Somerville. Washer/Drier in Basement. Common living room and kitchen. Close to Boston and Tufts, Harvard, and MIT via MBTA buses and T connections. Easy access to multiple bus routes. Only an easy 10-15 minute walk to the shops,...
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    Somerville, Massachusetts 02145
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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    Single bed room in home.1 / 6
    (1)Average
    Arlington
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Patio
    • Parking
    • Grill
    • Shared Garden
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 15, 2017
    Finding the house with people other than the owner was a surprise. House cat took exception to the fact I wouldn't let it in my room.
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    About this property
    This is a nice bedroom with a single bed in a home. Great safe, quiet location minutes to Harvard Square by bus. Walk to restaurants. Lovely outdoor living areas and gardens. 1 minute walk to bus. Shared bathroom. Boston has lots to offer and I am happy to help you plan your stay. Free off street...
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    Arlington, Massachusetts 02476
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 1
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    Somerville
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private room (shared bathroom) available in huge (1000+ sq. ft.) 4 bedroom/2 bath condo in Winter Hill area of Somerville. The condo features a large living room, a gorgeous kitchen with stainless steel appliances and granite counters, central air, and a washer & dryer. We can provide whatever...
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    Somerville, Massachusetts 02145
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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    4 BR Medford Square
    Medford
    4 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious 4 bedroom house at Medford square. Close to Tuffs University.
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    Medford, Massachusetts 02155
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 4
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    Somerville
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a two level 2 Bed, 2.5 Bath fully furnished house with spacious living room, kitchen and half-bath on the lower level and 2Bedrooms, bathroom on the top level and a completely renovated basement with full bathroom. Newly renovated hardwood floor, freshly painted, well-decorated and full...
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    Somerville, Massachusetts 02145
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    Somerville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • Housekeeping Included
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 3 bed, 2 bath, townhouse is business ready with wifi, 50inch tv with full cable, keurig & coffee/tea and flexible check-ins. We have a stock of DVDs, blowdryer, iron, universal charging station, a collection of frequent forgettables from all our travels, and hand written guides to Cambridge,...
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    Somerville, Massachusetts 02143
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Somerville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you looking for something In town for a night or a long weekend? Do not break the bank! Come stay in our. Immaculately maintained, incredibly big, bright and airy. Non-traditional setting in Somerville location: walking distance to MBTA, Assembly Row, award-winning bars and restaurants. Hop,...
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    Somerville, Massachusetts 02143
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Malden
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Malden 4BDR/1BA 2 driveway parking This is a beautiful three-bedrooms two family house in 5 mi. from Boston perfect for friends or families traveling to Boston! The 1200 SF area with a large living room & eat in kitchen, bedrooms and a front and back yard gives guests enough reason for enjoying...
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    Malden, Massachusetts 02148
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Arlington
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amsden Place is located on a quiet suburban side street with all the luxuries of home such as a kitchen, dishes, wine glasses, silverware and cups, microwave, stove, toaster, coffee-maker, refrigerator and freezer, washing machine, formal dining room, desk, free WiFi, cable TV in three rooms,...
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    Arlington, Massachusetts 02474
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Malden
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    Pet friendly
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    About this property
    Newly renovated studio with private entrance and parking. nice quiet neighborhood. Two minutes from route 1 ; 10 minutes from Rte 128/I95, and a 15 minute drive to airport. Bus stop is a 10 minute walk and takes you to the T (orange line) to Boston Everything new and all on your own floor, not...
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    Malden, Massachusetts 02148
    Condo/Apartment - 1 Bathroom, Sleeps 3
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