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.

Filter by Region:


Filter by Amenities:


Filter by Entertainment:


Close Filters

Search results

  1. 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

    $87 to $106/night

  2. 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

  3. HOUSE
    Spacious Home in Hyannis

    Spacious Home in Hyannis

    Hyannis, MA

    INSIDE THE HOUSE The homey living room features polished hardwood floors throughout. A comfy love seat and couch offer seating for 6, and there’s a 32” TV with cable for your evening entertainment. A bright dining area offering seating for...

    FREE CANCELLATION

    $195 to $587/night

  4. HOUSE
    73 Sequat House at Harwich

    73 Sequat House at Harwich

    Harwich, MA

    Business : nearby atm, nearby post office, nearby internet cafe, nearby bank Living : central air, air conditioning, ceiling fans, linens, washer & dryer, ironing board, high speed internet, fireplace, iron, hair dryer, cable, dvd, games, heat Local...

    Pets OK
    FREE CANCELLATION

    $488 to $1,473/night

  5. HOUSE
    Carpe Diem at Nantucket Retreats

    Carpe Diem at Nantucket Retreats

    Nantucket, MA

    Overlook the moors of Forever Wild Sanctuary and Polpis Harbor from Carpe DiemNew for 2019 - Pool and fire pit! The photos in the photo gallery of the pool and fire pit are included only to show what the finished product will look like. These few...

    Pool Hot Tub

    $2,686 to $5,204/night

  6. HOUSE
    Wooded Chatham Home on the Monomoy

    Wooded Chatham Home on the Monomoy

    Chatham, MA

    Wooded 3BR, 2BA Chatham Home on the Monomoy with Hot Tub & Kayak Launch This peaceful 3BR, 2BA woodland Chatham home (sleeps 6) is located right on the Monomoy River. Patio doors open to the travertine stone terrace, where a hot tub overlooks the...

    Hot Tub
    FREE CANCELLATION

    $249 to $498/night

  7. HOUSE
    40 Major Doane Rd Home

    40 Major Doane Rd Home

    Wellfleet, MA

    Welcome to this ideal 5BR/2.5BA Wellfleet getaway in a quiet, residential cul-de-sac less than 2 miles from the town pier and Cahoon Hollow Beach on the Cape Cod National Seashore. With three decks for breathing in the salty sea air, three levels of...

    FREE CANCELLATION

    $232 to $626/night

  8. 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

    $110 to $124/night

  9. HOUSE
    Colbyco Sand Hills Beach- Scituate

    Colbyco Sand Hills Beach- Scituate

    Scituate, MA

    Gorgeous new home on the ocean near Boston and Cape Cod. The Lions’ Den is a 4800 square foot gorgeous new home located in Scituate, MA – close to both Boston and Cape Cod. It features incredible views of the ocean with 6 decks and a widow's...

    Hot Tub

    $1,160 to $1,972/night

  10. HOUSE
    85 Cynthia Lane Home

    85 Cynthia Lane Home

    Dennis Port, MA

    Property Overview  Within walking distance of the local beaches and downtown Dennis Port, this 3BR/2BA home provides the ultimate coastal getaway. Freshly updated, your inviting retreat includes all-new furniture, new LED TVs with cable, and...

    FREE CANCELLATION

    $161 to $485/night

  11. HOUSE
    35 Timberlane Drive Home

    35 Timberlane Drive Home

    Mashpee, MA

    Nestled right on Santuit Pond, this charming 3BR/3BA home is the perfect Cape Cod getaway for a family or group of friends. Stairs lead down to a private floating dock where you can launch the provided kayaks. Rent jet skis or sailboats for even...

    FREE CANCELLATION

    $189 to $557/night

  12. HOUSE
    25 Doane Home at Harwich Port

    25 Doane Home at Harwich Port

    Harwich Port, MA

    Enjoy a peaceful Cape Cod country setting at this newly remodeled 3BR/2BA home, featuring hardwood floors and vibrant interior design elements. Entertain on the private deck in the fenced yard, equipped with a fire pit and a grill as well as an...

    Pets OK
    FREE CANCELLATION

    $166 to $436/night