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. 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

  2. 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

  3. HOUSE
    Colbyco Morton Park- Plymouth

    Colbyco Morton Park- Plymouth

    Plymouth, MA

    Charming lake front property in historic Plymouth Massachusetts. 4 Bedrooms, 2 full bathroom, sleeps 8 Charming four bedroom lake front vacation rental in historic Plymouth Massachusetts. Close to Cape Code and Boston, MA. Plymouth holds a place of...

  4. HOUSE
    Eastham Gem Home 190

    Eastham Gem Home 190

    Eastham, MA

    Property Overview  This welcoming 4BR/1.5BA cottage in Eastham offers the ultimate coastal getaway. Supremely located between the tranquil bay-side beaches and invigorating dunes and ocean waves of Nauset Light Beach, this home has it all,...

    FREE CANCELLATION

    $250 to $559/night

  5. 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

    $168 to $564/night

  6. HOUSE
    Scenic Bourns Pond House

    Scenic Bourns Pond House

    East Falmouth, MA

    This classic Cape-style 4BR/2BA is perched on the shore of the saltwater Bourns Pond, offering 180-degree water views from your own backyard. With west-facing windows, you can end every evening with a view of the sunset over the water. On lazy...

    FREE CANCELLATION

    $600 to $633/night

  7. HOUSE
    C394 Rocheleau

    C394 Rocheleau

    Charlestown, RI

    A delightful quintessential New England cottage. Views to Green Hill Pond. Launch a canoe across the street. 1/2 mile walk or cycle to beach. Quiet cul-de-sac lane. Charlestown is a town of beaches, marinas and salt ponds and offers many options for...

    $183 to $275/night

  8. HOUSE
    32 Crosby Lane House

    32 Crosby Lane House

    Falmouth, MA

    Perched on a hill overlooking the tidal Moonakis River, Osprey Point is a 3BR/2.5BA remodeled builder’s home offering a peaceful retreat for six. With three living areas and a sprawling backyard, there’s plenty of room to gather and have fun....

    FREE CANCELLATION

    $394 to $498/night

  9. 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

  10. 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

  11. 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

    $173 to $502/night

  12. HOUSE
    29 Shore Road Ext Home

    29 Shore Road Ext Home

    West Harwich, MA

    Property Overview  Nestled on a peaceful oceanside road, this single-story 4BR/3BA home features vaulted beam ceilings, a gourmet kitchen, and brick fireplace. Dine al fresco on the private patio or relax in the sunroom with a good book. Enjoy a...

    Pets OK
    FREE CANCELLATION

    $513 to $874/night

  13. 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

  14. 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

  15. HOUSE
    56 S Yarmouth Rd Home

    56 S Yarmouth Rd Home

    Dennis, MA

    Property Overview  Soak up the sun on nearby beaches, play games in the backyard, and gather around a fire pit in the evening at this welcoming two-level 3BR/2BA home. Crafted with hardwood floors and a gorgeous kitchen, you’ll find lots of...

    FREE CANCELLATION

    $131 to $473/night

  16. 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

    $195 to $658/night

  17. HOUSE
    C409 Tricarico

    C409 Tricarico

    Charlestown, RI

    Bright and cheerful well maintained beach cottage with partial ocean and Ninigret pond views! Nice open kitchen,dining ,living room area with two sliders that take you out onto the wrap around deck for summer enjoyment on those sunny days and...

  18. HOUSE
    C289 Boullianne

    C289 Boullianne

    Charlestown, RI

    Walk, bike or drive ¾ miles to Charlestown Beach from this 1800 sq ft spacious, light filled 5 bedroom, 2 bath Colonial situated on an acre of land. With a beach house such as this, you will never lack for space sitting around the kitchen table and...

    $263 to $336/night

  19. HOUSE
    C354 Munier (2-Bedroom Home)

    C354 Munier (2-Bedroom Home)

    Charlestown, RI

    Close to the beach - less than a mile - with an association beach parking pass and plenty of room. This house has window air conditioners and internet access. There is an amazing and very private back yard with deck and large, enclosed outdoor...

    $202 to $293/night

  20. HOUSE
    C390 Hall (2-Bedroom Home)

    C390 Hall (2-Bedroom Home)

    Charlestown, RI

    Start making those summer vacation memories in this very sweet cottage. This charmer was tastefully redone to include hardwood floors, stainless steel appliances and large outside shower. Home offers a private backyard for enjoying grilling and al...

    $110 to $214/night

  21. HOUSE
    C307 Flanagan

    C307 Flanagan

    Charlestown, RI

    Enjoy your family vacation at this Green Hill Pond waterfront home. The home is in the process of being completely remodeled and new photos will be submitted by May. The renovations are all of high quality and will transform this already charming...

    $355 to $526/night

  22. HOUSE
    C037 Pape (2-Bedroom Home)

    C037 Pape (2-Bedroom Home)

    Charlestown, RI

    Great location to have a relaxing summer vacation where memories are made. The kitchen is fully equipped. Lounge in Living room or grill on deck. This two bedroom with loft sleeps eight people. One bedroom has a queen bed and the other bedroom has 2...

  23. HOUSE
    C371 Garro (3-Bedroom Home)

    C371 Garro (3-Bedroom Home)

    Charlestown, RI

    Walk to ocean beach from this ranch cottage located in charming Sea Lea Colony. Also, for a change of pace, you can sit on the viewing deck located on the roof & enjoy the view along with your summer cocktail and watch the beautiful sunsets. In...

    $183 to $306/night

  24. HOUSE
    C347 Wilson (2-Bedroom Home)

    C347 Wilson (2-Bedroom Home)

    Charlestown, RI

    Oceanfront in Charlestown - walk directly out into the warm sand and enjoy swimming, sun bathing, surf fishing, building a sandcastle; or, a stroll on the beautiful beach. For those that want to reserve their energy, there's "people watching" from a...

  25. HOUSE
    C386 Dispoto

    C386 Dispoto

    Charlestown, RI

    Located just 1/2 mile from beautiful Charlestown Town Beach. This spacious Raised Ranch offers comfortable sleeping for 8 to 10 people. The main living level has two large bedrooms, one with Queen and the master bedroom with a King bed, There is a...

  26. HOUSE
    C392 Charlestown on the Beach

    C392 Charlestown on the Beach

    Charlestown, RI

    Feel the ocean breezes and hear the waves from this wonderful three bedroom home on Charlestown Beach. Watch the sun rise and set from the large comfortable deck that has multiple tables with umbrellas and seating all around. A few steps down the...

    $734 to $874/night

  27. HOUSE
    West Harwich House #10

    West Harwich House #10

    West Harwich, MA

    This charming 3-bedroom, 2-bath (sleeps 8) West Harwich House is less than a mile from Pleasant Road Beach and its gentle waves and wide, sandy shoreline. Recently remodeled with cathedral ceilings, an open-concept design, and big bright windows...

    FREE CANCELLATION

    $346 to $473/night

  28. APARTMENT
    Roseclair at Upham's Corner

    Roseclair at Upham's Corner

    Boston, MA

    Property Description Fully furnished luxury apartment centrally located in Boston near the historic South End 3 Bedrooms/1 Bathroom Bedrooms have queen beds Full Kitchen Free Wifi Designer furnishings create an elegant coziness throughout The...

    Pets OK
    FREE CANCELLATION

    $215 to $488/night

  29. APARTMENT
    206 on Washington Apartment

    206 on Washington Apartment

    Jamaica Plain, Boston, MA

    The 206 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

    $194 to $418/night

  30. APARTMENT
    404 on Parker Hill Apartment

    404 on Parker Hill Apartment

    Boston, MA

    540 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

    $214 to $384/night