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. DUPLEX
    460 Lower County Road Duplex Left Side Unit

    460 Lower County Road Duplex Left Side Unit

    Dennis Port, MA

    This single-story 3BR cottage is a quaint getaway offering superb outdoor space. Relax on the front porch and host a fun cookout in the large backyard. An outdoor shower is great for rinsing sandy toes after a fun beach day. Walk across the street...

    FREE CANCELLATION

    $106 to $260/night

  2. HOUSE
    Corner Lot Home

    Corner Lot Home

    South Yarmouth, MA

    Situated on a corner lot with views of James Pond from nearly every room, this 4BR/2BA house offers a tranquil retreat. Affording a walkable locale, you’ll love being a pleasant stroll from Long Pond as well as local restaurants and attractions....

    FREE CANCELLATION

    $132 to $475/night

  3. DUPLEX
    Lower County Road Duplex

    Lower County Road Duplex

    Dennis Port, MA

    Host your next family get together at this quaint 6BR/2BA duplex cottage. This rental includes two identical side-by-side units -- each with a full-size kitchen, living area, and awesome outdoor space. Hang out on comfy furniture on the front porch...

    FREE CANCELLATION

    $211 to $516/night

  4. DUPLEX
    460 Lower County Road Duplex Right Side Unit

    460 Lower County Road Duplex Right Side Unit

    Dennis Port, MA

    Walk everywhere from this cute 3BR cottage! Enjoy an amazing outdoor space, including a quintessential front porch with lounge furniture and a shared yard that has an outdoor shower, grill, and shaded al fresco dining. Your rental commands a prime...

    FREE CANCELLATION

    $106 to $260/night

  5. HOUSE
    Daisy Street Home 12

    Daisy Street Home 12

    Harwich, MA

    Boasting classic Cape Cod style and a prime location just 200 steps from Long Pond, this 4BR/2BA cottage offers the perfect home base for your vacation. Spend your days fishing, swimming, and boating on Long Pond, the largest freshwater lake on Cape...

    FREE CANCELLATION

    $185 to $415/night

  6. HOUSE
    Cape Cod Bay Home

    Cape Cod Bay Home

    Eastham, MA

    With 2,785 square feet of living space, this two-story Eastham home offers abundant social space with two living areas and a large deck. A huge, open kitchen makes it easy to prep meals for your entire group. In a prime location, you’ll be within...

    FREE CANCELLATION

    $158 to $658/night

  7. HOUSE
    34 Salt Spray Home

    34 Salt Spray Home

    South Chatham, MA

    With two levels of living space, this completely remodeled 3BR/2BA home features radiant heating, high-end appliances, and custom cabinetry. Abundant natural light abounds with large windows, French glass doors, and a multitude of skylights....

    FREE CANCELLATION

    $264 to $459/night

  8. HOUSE
    Woodsy Haven Home

    Woodsy Haven Home

    East Sandwich, MA

    Just 3 miles from Sandy Neck and 6 miles to stunning Boardwalk Beach, this lovely 4BR/2.5BA home is tucked away on a private, wooded lot. From the open-concept main floor to the spacious deck and master balcony, there's plenty of space indoor and...

    Pets OK
    FREE CANCELLATION

    $132 to $564/night

  9. HOUSE
    356 Deer Meadow Lane Home

    356 Deer Meadow Lane Home

    Chatham, MA

    Six beaches are within a 10-minute drive of this recently renovated 3BR/2.5BA Chatham home, tucked in a quiet neighborhood ideal for morning walks and bike rides. The light-filled interior includes a peaceful master suite and a sunroom, and the...

    FREE CANCELLATION

    $142 to $502/night