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Winthrop Romantic Vacation Rentals

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    33 Matching Rentals in the Winthrop AreaView all 643 rentals
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    The following rentals are within 5 miles of Winthrop.
    Location and Luxury North End 2 Bedroom Apartment - 1,000 Sq. ft!1 / 22
    (3)Excellent
    Boston
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Luxury Boston Studio w/ Brand New Kitchen1 / 9
    (1)Very good
    Boston
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Boston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Luxury Suite, Moroccan Furnishings, Boston1 / 97
    (16)Excellent
    Boston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Shared Yard
    • Housekeeping Included
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 30, 2015
    The place is amazing. It's clean and comfortable. The owners are very friendly and willing to accommodate all your needs. We hade such a great time. Highly recommended and we'll...
    Reviewed January 31, 2015
    My wife and I spent a portion of our honeymoon at this Bed & Breakfast and it was absolutely amazing!!! I can't say enough good things about Elizabeth and how well she...
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    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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    Arthouse - Boston Brewery District Condo1 / 24
    (17)Very good
    Boston
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Parking
    • Shared Yard
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 14, 2018
    The location is an easy walk to the Metro Station which takes you right into the heart of Boston. We went with friends so there were two couples sharing this accommodation...
    Reviewed September 21, 2017
    A perfect place to stay for getting around Boston. Arthouse is a well appointed and comfortable apartment. Certainly a relaxing place to come back to after being out and about...
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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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    Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Indoor Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just steps away from Boston Common, each high-end Stay Alfred on Washington Street makes the perfect Boston vacation rental for business or leisure travelers who want all the comforts of home. Think of it as your place in the city, with a full kitchen, in-unit laundry, and easy access to public...
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    Boston, Massachusetts 02116
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Boston
    Studio, 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 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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    Boston, Massachusetts 02113
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Boston
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Indoor Pool
    • Cable/satellite TV
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just steps away from Boston Common, each high-end Stay Alfred on Washington Street makes the perfect Boston vacation rental for business or leisure travelers who want all the comforts of home. Think of it as your place in the city, with a full kitchen, in-unit laundry, and easy access to public...
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    Boston, Massachusetts 02116
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Boston
    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
    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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    Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Indoor Pool
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just steps away from Boston Common, each high-end Stay Alfred on Washington Street makes the perfect Boston vacation rental for business or leisure travelers who want all the comforts of home. Think of it as your place in the city, with a full kitchen, in-unit laundry, and easy access to public...
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    Location Information
    Boston, Massachusetts 02116
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Indoor Pool
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just steps away from Boston Common, each high-end Stay Alfred on Washington Street makes the perfect Boston vacation rental for business or leisure travelers who want all the comforts of home. Think of it as your place in the city, with a full kitchen, in-unit laundry, and easy access to public...
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    Location Information
    Boston, Massachusetts 02116
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Boston
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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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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    Romantic 1BR in Downtown Crossing by Sonder1 / 24
    (1)Terrible
    Boston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the chic decor, fully-equipped kitchen, and private master 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 02116
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Elegance at Salem Court, Boston1 / 59
    (13)Excellent
    Boston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Yard
    • Air Conditioning
    • DVD Player
    • Housekeeping Included
    • Outdoor Dining Area
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 3, 2017
    I stayed for a week in Boston and the location was ideal to get away from the hustle and bustle of downtown. Charlestown is easily accessible from the airport by taxi and...
    Reviewed February 27, 2017
    My fiance and I have stayed at The Moroccan Suites five times over the last two years and it is our favorite place to stay in Boston! We have stayed in all of the rooms, but the...
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    About this property
    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 Hill, USS Constitution,...
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    Location Information
    Boston, Massachusetts 02129
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Chic South End, Back Bay, Downtown Boston Apartment1 / 13
    (2)Excellent
    Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Washer
    • Grill
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 14, 2018
    Cassandra is an awesome host!! Her apartment is extremely clean, and has a very “at home” feel to it. You can’t beat the location! Close to tons of restaurants, bars, public T...
    Reviewed February 13, 2017
    Cassandra and Mike's apartment was perfect! Check-in was a breeze and they were great hosts. They had a booklet full of info about the area, things to do, places to eat etc.The...
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    About this property
    Our apartment is located in the South End, Boston; a vibrant area famous for its Victorian brick row houses and the best restaurants in Boston! Get some dinner, drinks & shop at Newbury Street, Back Bay, Copley, Prudential, & Downtown Crossing, all located within 1 mile. Catch a game or event at...
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    Location Information
    Boston, Massachusetts 02118
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Golden Slipper,  B&B Afloat and Charter1 / 23
    (53)Excellent
    Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Air Conditioning
    • DVD Player
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 24, 2018
    We stayed in the Golden Slipper towards the latter end of a 3-week tour in the USA. We wanted our own corner to relax in, our own space in which to have a slow start each day if...
    Reviewed July 25, 2018
    Thank you for a fantastic experience! We love Boston, it is such a beautiful city and we have stayed in hotels all over town, but never on a yacht docked next to the fabulous...
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    About this property
    *** Celebrating 27 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Boston
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Terrace
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Downtown, the heart of Boston and...
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    Location Information
    Boston, Massachusetts 02127
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Boston
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Waterfront
    • Balcony
    • Terrace
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Revere's house & the Old North...
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    Location Information
    Boston, Massachusetts 02109
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    ASTONISHING 1 BEDROOM IN SOUTH END BOSTON'S BEST LOCATION & CLOSE TO EVERYTHING1 / 33
    (1)Excellent
    Boston
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Me and my husband stayed at this apartment for a week in September and it was truly wonderful, the best rented accommodation I have ever stayed in. It had everything we needed...
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    About this property
    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 in the city. Famous bakeries,...
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    Location Information
    Boston, Massachusetts 02118
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Boston
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
    • Internet Access
    • Cable/satellite TV
    • Terrace
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    North End, Luxury Condo apartment 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...
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    Location Information
    Boston, Massachusetts 02109
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Arthouse 2 Artist/Brewery District1 / 6
    (1)Very good
    Boston
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 12, 2017
    We stayed for 5 nights on our way back from Maine after a family wedding where we were meeting other family . The apartment was well equipped & comfortable . When we arrived...
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    About this property
    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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    Location Information
    Boston, Massachusetts 02130
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Boston
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    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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    Green Turtle II Yacht in Boston Harbor - #1 B & B -Tripadvisor since 20101 / 9
    (21)Excellent
    Boston
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Waterfront
    • DVD Player
    • Outdoor Dining Area
    • Housekeeping Included
    • Cable/satellite TV
    • Air Conditioning
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 21, 2017
    Awesome stay!!!Beautiful view and wonderful hosts. We very much enjoyed our stay and recommend the Green Turtle!
    Reviewed June 15, 2017
    My family and I stayed at the Green Turtle II Bed and Breakfast on June 9th & 10th, 2017. The boat had plenty of space to accommodate the 5 of us with 2 bedrooms and 2...
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    About this property
    The Green Turtle has been Boston's #1 Bed and Breakfast in Boston every day since August of 2010. We were also chosen as a Tripadvisor Traveler's Choice award in 2014 which is 1 of top 25 in US! The Green Turtle II is a floating bed and breakfast as luxurious as it is unique. Green Turtle II is...
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    Boston, Massachusetts 02129
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Boston
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is located at East Boston close to Logan airport, only 2 stops away from airport via Blue Line subway. Get off at Orient Heights station and then walk about 5 minutes. Take same Blue Line subway easy reach downtown Boston, the city center, parks, beach and art and culture. You’ll love my...
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    Boston, Massachusetts 02128
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Sophisticated, centrally located West End condo w/ shared swimming pool & gym1 / 28
    (2)Very good
    Boston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 29, 2017
    It is a very spacious apartment and handy to different interesting sights around Boston. We also liked having Whole Foods supermarket nearby where we could buy fresh ready...
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    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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    Location Information
    Boston, Massachusetts 02114
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Boston
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Boston's hottest neighborhood!- Just steps to some of the top restaurants & lounges in the city, The ICA, Boston's World Trade Center, The Blue Hills Bank Pavilion & Boston's Convention & Exhibition Centers. Accessible via public transport-Less than 10min walk from MBTAs South Station,...
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    Location Information
    Boston, Massachusetts 02210
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Boston
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
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    Pet friendly
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    About this property
    Clean, spacious two bedroom is close to Ashmont Village, UMASS Boston & Downtown Boston. You’ll love the Quiet neighborhood with included off-street parking a short drive, uber or train ride to downtown. My place is good for couples and families. Lots of restaurants and bars in the neighborhood....
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    Location Information
    Boston, Massachusetts 02122
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Boston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This is a perfect and cozy one bedroom in the heart of historic Beacon Hill. My place is close to Charles River Esplanade, Faneuil Hall, Freedom Trail, Tip Tap Room, and Savenor's Market. You’ll love my place because of the views, the high ceilings, and the comfy bed. My place is good for couples,...
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    Location Information
    Boston, Massachusetts 02114
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Boston
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    About this property
    This brick New England style home is located on a quite tree-lined dead-end street adjacent to reservation area around Chestnut Hill Reservoir. Steps to Boston College, direct trains to Boston University, Downtown Boston, Medical Area and direct bus to Cambridge Harvard Square and Harvard...
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    Boston, Massachusetts 02135
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Boston
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Cable/satellite TV
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    • Balcony
    • DVD Player
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    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New! Walk to beach, only 600 feet away! This gorgeous, newly remodeled home has the best of everything, is only steps to Englewood Beach, and is now being offered as a summer weekly rental! Here is your chance to have it all, including a beautifully updated kitchen offering all the comforts of...
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    Location Information
    Boston, Massachusetts 02673
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Boston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Grill
    • Washer
    Suitability
    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Boston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Patio
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    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    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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    Location Information
    Boston, Massachusetts 02127
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Parking
    • DVD Player
    • Washer
    • Air Conditioning
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are planning a trip to Boston consider staying on our very comfortable motor yacht 'Sea Pearl' in historic Charlestown on Boston Harbor. We are located in the new Charlestown Marina close to the USS Constitution, Freedom Trail and Bunker Hill monument. The North End is a very pleasant walk...
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    Location Information
    Boston, Massachusetts 02129
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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