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When it comes to lobster rolls and New England clam chowder, nobody can touch Massachusetts. Shrouded in history, the Bay state is well known as the birthplace of the American revolution, the Freedom Trail, and the Boston Tea Party. Seafood, history, the Red Sox- Massachusetts has it all. RedAwning will help you find the perfect vacation rental to complete your East Coast experience. Browse your favorite Massachusetts region using the blue location links below, or filter your preferences using the panel on the side. With our simplified booking process, you'll have the most important part of your trip buttoned in no time.
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  1. HOUSE
    Colbyco Oceanside- Scituate

    Colbyco Oceanside- Scituate

    Scituate, MA

    Spectacular Colonial where you wake up to the sound of the waves and unobstructed ocean views! Wake up to the sound of the waves as you take in the unobstructed ocean views! This spectacular newer (2013) colonial features the best in craftsmanship,...

    $847 to $847/night

  2. CONDOMINIUM
    Bentley Brook Studio

    Bentley Brook Studio

    Hancock, MA

    The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting...

    Pool Hot Tub
  3. CONDOMINIUM
    Bentley Brook 2 Bedroom

    Bentley Brook 2 Bedroom

    Hancock, MA

    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the...

    Pool Hot Tub

    $195 to $227/night

  4. CONDOMINIUM
    Third at Third Apartment #1708

    Third at Third Apartment #1708

    Cambridge, MA

    This property is located in the heart of Kendall Square, an award winning neighborhood marked as a global center for innovation and cutting edge technology next to MIT.Dubbed as one of the most exciting places to live, work, shop and play in the...

    Pets OK
    FREE CANCELLATION

    $353 to $430/night

  5. CONDOMINIUM
    Kendall at Third Apartment #1502

    Kendall at Third Apartment #1502

    Cambridge, MA

    This property is located in the heart of Kendall Square, an award winning neighborhood marked as a global center for innovation and cutting edge technology next to MIT.Dubbed as one of the most exciting places to live, work, shop and play in the...

    Pool Pets OK
    FREE CANCELLATION

    $321 to $430/night

  6. CONDOMINIUM
    Tremont at Tremont Apartment #307

    Tremont at Tremont Apartment #307

    Boston, MA

    We are near it all! The Tremont has great access to both the Orange Line and Green Line subways, Route 66 Bus line, as well as several convenient Hubway Bike share stations. Being just a short walk from Brigham Circle and the Longwood Medical Area,...

    Pets OK
    FREE CANCELLATION

    $405 to $450/night

  7. CONDOMINIUM
    Garrison at Garris Apartment #307

    Garrison at Garris Apartment #307

    Boston, MA

    Now you can truly live like a local in our newly furnished Go Local suites! All of the furniture, artwork, and housewares have all been sourced locally and are all 100% made in the United States!All of the furniture is high quality craftsmanship and...

    Pets OK
    FREE CANCELLATION

    $346 to $391/night

  8. CONDOMINIUM
    Lewis at Lewis Str Apartment #115

    Lewis at Lewis Str Apartment #115

    East Boston, MA

    Accessible Studio Apartment at East PierBeautiful brand new construction located in East Boston, just a minute walk to the Maverick Blue Line Subway Stop, which is just one stop to Downtown Boston / State Street. Also nearby is Logan Airport, just a...

    Pets OK
    FREE CANCELLATION

    $209 to $321/night

  9. CONDOMINIUM
    East Pier at Margi Apartment #2131

    East Pier at Margi Apartment #2131

    East Boston, MA

    Executive Studio in East BostonBeautiful brand new construction located in East Boston a little over 2 miles from Boston's city center and just a minute walk to the Maverick Blue Line Subway Stop, which is just one stop to Downtown Boston / State...

    Pool Pets OK
    FREE CANCELLATION

    $257 to $347/night

  10. CONDOMINIUM
    Kendall at Third South Apartment #205

    Kendall at Third South Apartment #205

    Cambridge, MA

    This property is located in the heart of Kendall Square, an award winning neighborhood marked as a global center for innovation and cutting edge technology next to MIT.Dubbed as one of the most exciting places to live, work, shop and play in the...

    Pets OK
    FREE CANCELLATION

    $347 to $416/night

  11. CONDOMINIUM
    Fisher at Fisher Aven Apartment #203

    Fisher at Fisher Aven Apartment #203

    Boston, MA

    Brand New Property in Mission HillMission Hill's newest gem is just steps away from it all. Nestled in the heart of Mission Hill, this apartment community is in the hustle and bustle of the city, yet away from the noise and chaos. Featuring modern...

    Pets OK
    FREE CANCELLATION

    $398 to $501/night

  12. HOUSE
    C047 Sol (2-Bedroom Home)

    C047 Sol (2-Bedroom Home)

    Charlestown, RI

    Charlestown Beach. Sit on the deck and enjoy the beautiful views of the ocean and Block Island. There are no houses in front of you to block the views. There is a private walkway across the sand dune that takes you to the beach where you can jump...

    $318 to $489/night

  13. HOUSE
    C129 Albert (3-Bedroom Home)

    C129 Albert (3-Bedroom Home)

    Charlestown, RI

    A vacation spot where memories are made! Come and enjoy family time at this spacious 1700 sqft home by the beach. The house is newly remodeled features hardwood flooring, newly carpeted bedrooms, renovated baths.New kitchen has granite counterops...

    $306 to $306/night

  14. HOUSE
    C222 Shafer (4-Bedroom Home)

    C222 Shafer (4-Bedroom Home)

    Charlestown, RI

    This spacious Colonial, located on a quiet dead end street, offers large, sun-filled rooms that are nicely furnished and ideal for a large group of up to 10 guests. Gather in the open kitchen/dining/family room or have quiet conversation in the den....

    $440 to $440/night

  15. HOUSE
    C291 Reeb (1-Bedroom Home)

    C291 Reeb (1-Bedroom Home)

    Charlestown, RI

    Ocean views are captured by the sun-filled windows; waves lull you to sleep, miles of fabulous wide sandy beach steps from the front door. Bright, light and all refurbished in 09-new kitchen. Seafood dining "al fresco" around the corner... fishing,...

    $483 to $483/night

  16. HOUSE
    C359 Matos (5-Bedroom Home)

    C359 Matos (5-Bedroom Home)

    Charlestown, RI

    This 5 bedroom, 2 bath gem has room for the whole family to vacation in comfort. A recent interior renovation offers updates everywhere. An extra large deck overlooking the acre of back yard lends itself to summer fun and entertaining. New outside...

    $245 to $245/night

  17. HOUSE
    C368 Dudek (3-Bedroom Home)

    C368 Dudek (3-Bedroom Home)

    Charlestown, RI

    Beach Pass to Blue Shutters and Charlestown Town Beach. Charming and spacious three bedroom Cape with central air and nice hardwood floors thru out. Large spacious bright living room with wall of atrium doors and windows that welcomes in the gardens...

    $171 to $367/night

  18. HOUSE
    C384 Buckley

    C384 Buckley

    Charlestown, RI

    Begin making those vacation memories in this seaside cottage . Nicely furnished , this one level home has open kitchen & living area , large deck and an outside shower to rinse off that beach sand . Sleeping accommodations for 6 . Master bedroom has...

    $177 to $324/night

  19. HOUSE
    W091 Vaccaro

    W091 Vaccaro

    Charlestown, RI

    We welcome you to enjoy our family cottage nestled in the woods and just a 10 minutes from the beach. Our place has a large backyard with plenty of shade and privacy. Take advantage of our deck and patio on our one acre lot. Feel free to gather...

    $134 to $134/night

  20. HOUSE
    C024 Broccoli

    C024 Broccoli

    Charlestown, RI

    This two story cottage offers tons of sleeping and generous sized rooms. Fresh, immaculate and cute. Large dining/sun bathing deck. 1 acre of yard, shed for the bikes. .75 of a mile to beach, 1/4 mile to ice cream, bakery & deli shops. "Sea Breeze...

    $318 to $440/night

  21. HOUSE
    C315 Broccoli 676

    C315 Broccoli 676

    Charlestown, RI

    Ocean front on Charlestown Beach. Make a lifetime of memories at this newly built beach house. Relax on the deck overlooking the Atlantic Ocean, Block Island, the Breachway and miles of one of South County’s most sought after beaches. Enjoy your...

    $581 to $844/night

  22. APARTMENT
    506 on Parker Hill Apartment

    506 on Parker Hill Apartment

    Boston, MA

    525 Sq Ft. Mission Hill Apartment, 1 bedroom, 1 bathroom, in unit washer dryer, central air/heating on Parker Hill in the Mission Hill Neighborhood. Full kitchen including dishwasher, disposal, coffee maker and pots and pans, Unit is brand new for...

    Pets OK
    FREE CANCELLATION

    $276 to $670/night

  23. APARTMENT
    201 on Washington Apartment

    201 on Washington Apartment

    Jamaica Plain, Boston, MA

    The 201 at 3389 Washington St. is a recent addition to the Jamaica Plain neighborhood where the original Sam Adams Brewery is located. Each unit is brand new and features a washer/dryer, private patio access, full kitchen including dishwasher,...

    Pets OK
    FREE CANCELLATION

    $333 to $742/night

  24. APARTMENT
    306 on Parker Hill Apartment

    306 on Parker Hill Apartment

    Boston, MA

    525 Sq Ft. Mission Hill Apartment, 1 bedroom, 1 bathroom, in unit washer dryer, central air/heating on Parker Hill in the Mission Hill Neighborhood. Full kitchen including dishwasher, disposal, coffee maker and pots and pans, Unit is brand new for...

    Pets OK
    FREE CANCELLATION

    $276 to $670/night

  25. HOUSE
    SeaWatch

    SeaWatch

    Nantucket, MA

    SeaWatch is an oceanfront dream in Quidnet Treat your group to a captain's view of the Atlantic Ocean and Sesachacha Pond at SeaWatch, an exceptional vacation rental at the edge of the ocean complete with beach access and a separate guest house....

    $1086 to $3406/night

  26. APARTMENT
    C400 Caswell

    C400 Caswell

    Charlestown, RI

    Beach: Blue Shutters Beach: Blue Shutters Beach, East Beach, Charlestown Beach, Ninigret Pond, Burlingame State Park/Watchaug Pond COMES WITH BEACH PASS TO BLUE SHUTTERS BEACH AND CHARLESTOWN BEACH Our place has a large backyard with plenty of...

    $153 to $153/night

  27. HOUSE
    C389 Lorenzo

    C389 Lorenzo

    Charlestown, RI

    Enjoy panoramic views of Charlestown Beach and Ninigret Pond from the upstairs level of this well cared for home! The large open space and vaulted ceiling on this floor make up the well equipped kitchen, dining, living room and half bath. Lots of...

    $544 to $544/night

  28. HOUSE
    Carpe Diem

    Carpe Diem

    Nantucket, MA

    Overlook the moors of Forever Wild Sanctuary and Polpis Harbor from Carpe Diem Arrive at this exceptional vacation property one of three ways: by car, by Wave shuttle/Polpis Route, or by the Polpis bike path. With a central location just a few miles...

    Pool Hot Tub

    $2869 to $5558/night

  29. COTTAGE
    C396 Schroeder

    C396 Schroeder

    Charlestown, RI

    Beach: West Beach *Classic Rhode Island beach cottage with full view of the ocean & Block Island * Located on private West Beach in Charlestown, RI *Rental comes with beach privileges * Porches on three sides for both shade and sun relaxing...

    Pets OK

    $202 to $202/night

  30. CONDOMINIUM
    Tremont at Tremont Apartment #406

    Tremont at Tremont Apartment #406

    Boston, MA

    The Valor is situated in Boston's Mission Hill neighborhood, .84 miles from Boston Museum of Fine Arts, .9 miles from Longwood Medical Area, 1.2 miles from Fenway Park, and just 5.6 miles away from Boston Logan International Airport.The Longwood...

    Pets OK
    FREE CANCELLATION

    $405 to $450/night