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
    803 Commercial St Home

    803 Commercial St Home

    Provincetown, MA

    Plan a beachfront getaway for twelve guests at this 5BR/3BA home, where generous picture windows afford water views from almost every room. Spend leisurely vacation days on the two-story patio overlooking Cape Cod Bay. With lounge seating, a gas...

    Pool Pets OK
    FREE CANCELLATION

    $1,225 to $2,145/night

  2. CONDOMINIUM
    Bentley Brook 1 Bedroom

    Bentley Brook 1 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
  3. 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
  4. CONDOMINIUM
    232 Billington Ln Condo

    232 Billington Ln Condo

    Brewster, MA

    You can have it all at Ocean Edge Resort & Golf Club. Step out from your 2BR/1.5BA condo and onto the beautiful fairway—the course was designed by Jack Nicklaus and makes for an incredible backdrop for an afternoon game or a bike ride. Ocean Edge...

    Pool
    FREE CANCELLATION

    $143 to $332/night

  5. 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
  6. APARTMENT
    Brookline Brownstone

    Brookline Brownstone

    Brookline, MA

    This 3 BR 2 BA apartment is fully updated and has in unit laundry. Good for couples, solo adventurers, traveling nurses, doctors, business travelers, families (with kids), and big groups. The apartment is minutes from Longwood Medical Area, home of...

    Pool Hot Tub Pets OK

    $183 to $444/night