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Boston Romantic Vacation Rentals

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    Travelers to Boston are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    21 Matching Rentals in BostonView all 403 rentals
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    Arthouse - Boston Brewery District Condo1 / 24
    (17)Very good
    Jamaica Plain / Mission Hill
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Elegance at Salem Court, Boston1 / 59
    (13)Excellent
    Charlestown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Boston Commoms supreme location/one bedroom1 / 25
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    The Golden Slipper,  B&B Afloat and Charter1 / 23
    (53)Excellent
    North End
    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 28 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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    ASTONISHING 1 BEDROOM IN SOUTH END BOSTON'S BEST LOCATION & CLOSE TO EVERYTHING1 / 33
    (1)Excellent
    South End
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 28, 2018
    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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    Luxury Suite, Moroccan Furnishings, Boston1 / 97
    (16)Excellent
    Charlestown
    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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    Location Information
    Boston, Massachusetts 02129
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    South 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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    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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    Chic South End, Back Bay, Downtown Boston Apartment1 / 13
    (2)Excellent
    South End
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • 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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    Dorchester / Roxbury / Mattapan
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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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    Jamaica Plain / Mission Hill
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    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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    Location Information
    Boston, Massachusetts 02130
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 4
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    Beacon Hill
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly Renovated! You will Love my 2 bedroom 2 bathroom apartment centrally located in this beautiful city! Walking distance to the many attractions Boston has to offer! Next to Faneuil Hall, New England Aquarium , Charles River Esplanade, Freedom Trail, TD Garden, Quincy Market. You’ll love my...
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    Location Information
    Boston, Massachusetts 02109
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Arthouse 2 Artist/Brewery District1 / 6
    (1)Very good
    Jamaica Plain / Mission Hill
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    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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    East Boston / Logan Airport
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    Suitability
    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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    Location Information
    Boston, Massachusetts 02128
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    2BR Boston Condo In the Heart of Back Bay!1 / 25
    (1)Very good
    Back Bay
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 7, 2017
    Apartment was in a fantastic location for exploring Boston. General areas like hall and stairway could do with updating but overall we were happy with the apartment.
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    About this property
    Treat yourself to a fantastic Beantown getaway with this 2-bed, 2-bath Boston condo, which sleeps 4! Perfect for small families, groups of friends, or couples traveling together, this beautiful home is close to downtown, contains high-end amenities, and is sure to suit all of your desires during...
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    Location Information
    Boston, Massachusetts 02116
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Balcony
    • DVD Player
    • Washer
    • 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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    Green Turtle II Yacht in Boston Harbor - #1 B & B -Tripadvisor since 20101 / 9
    (21)Excellent
    Charlestown
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Location Information
    Boston, Massachusetts 02129
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Allston / Brighton
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Boston, Massachusetts 02135
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Charlestown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay aboard our motor yacht. The really fun way to visit the city of Boston. Spend a busy day seeing the sites and return to your quiet spot on the water. Many of my guests comment on how they can not wait to return every night. The yacht works well for a family or two couples. Extra...
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    Location Information
    Boston, Massachusetts 02129
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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