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 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...

  2. HOUSE
    17 Finway House in New Seabury

    17 Finway House in New Seabury

    Mashpee, MA

    This newly renovated 3BR, 3BA New Seabury home offers classic New England charm with its beachy decor and cathedral ceilings. The ideal place from which to adventure into the outdoors, it’s just a stroll away from Jim Pond and 5 minutes from South...

    FREE CANCELLATION

    $212 to $607/night

  3. 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

    $1,740 to $1,972/night

  4. HOUSE
    Colbyco Dana Park- Cambridge

    Colbyco Dana Park- Cambridge

    Cambridge, MA

    Three story residential Townhouse. The structure was built in 1977, and the home is made up of approximately 1,360 square feet of livable space, and sits on about 1,632 square foot lot.While close to the MBTA Redline train station (Central Square),...

  5. 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

    $189 to $494/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

    $211 to $647/night

  7. 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

    $191 to $537/night

  8. 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...

  9. 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

  10. APARTMENT
    306 on Washington Apartment

    306 on Washington Apartment

    Jamaica Plain, Boston, MA

    All New for 2017! Wonderfully built brand new 820sq foot 1 bedroom/1 bath apartment in Jamaica Plain with patio! Minutes walk to gorgeous Jamaica Pond and the night life on Centre Street, 5 min walk to Subway! Dedicated parking, central air, gas...

    Pets OK
    FREE CANCELLATION

    $289 to $452/night

  11. APARTMENT
    3399 Washington Unit 2

    3399 Washington Unit 2

    Jamaica Plain, Boston, MA

    All New for March 2018! Wonderfully built brand new 3 bed / 2 bath apartment in Jamaica Plain with patio! Minutes walk to gorgeous Jamaica Pond and the night life on Centre Street, 5 min walk to Subway! Dedicated parking, central air, gas heat, in...

    FREE CANCELLATION

    $287 to $467/night

  12. CONDOMINIUM
    Grand View on Jones Hill

    Grand View on Jones Hill

    Boston, MA

    Property Description4 Queen Beds, 1 Single Bed 2 Bathrooms Fully furnished Free WIFI through a secure, password-protected router. Laundry room on the bedroom level with full washer/dryer Kitchen equipped with refrigerator, dishwasher, stove,...

    Pets OK
    FREE CANCELLATION

    $357 to $607/night

  13. 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

    $281 to $437/night

  14. APARTMENT
    Mayhew at Upham's Corner

    Mayhew at Upham's Corner

    Boston, MA

    The Mayhew is a third floor, fully furnished 1200sf luxury apartment centrally located in Boston near the historic South End. Part of a meticulous building restoration, the Mayhew combines characteristic turn-of-the-century Boston area architecture...

    Pets OK
    FREE CANCELLATION

    $281 to $449/night

  15. 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

    $264 to $400/night

  16. CONDOMINIUM
    Penthouse at Upham's Corner

    Penthouse at Upham's Corner

    Boston, MA

    The Penthouse is a fourth floor, fully furnished 1200sf luxury apartment centrally located in Boston near the historic South End. Part of a meticulous building restoration, the Penthouse combines characteristic turn-of-the-century Boston area...

    Pets OK
    FREE CANCELLATION

    $294 to $467/night

  17. 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

    $273 to $434/night

  18. HOUSE
    Water Views on Monomoscoy Island

    Water Views on Monomoscoy Island

    Mashpee, MA

    Our 3-bedroom, 2-bath Cape Cod on Monomoscoy Island, with ample back deck, enjoy water views and use of a small private beach, perfect for families. You’re just steps from the great swimming, clamming, and fishing that make for the quintessential...

    Pets OK
    FREE CANCELLATION

    $176 to $523/night

  19. HOUSE
    Oceanview Buzzards Bay Getaway

    Oceanview Buzzards Bay Getaway

    Bourne, MA

    This family-friendly 3BR/2.5BA beach house offers beautiful views of the ocean from the wraparound deck. Enjoy a relaxing stay in a peaceful and secluded neighborhood while still being steps away from beautiful beaches situated on either side of the...

    FREE CANCELLATION

    $175 to $610/night

  20. DUPLEX
    Beach-Central Cape Cod Duplex

    Beach-Central Cape Cod Duplex

    Dennis Port, MA

    A short walk from Dennisport’s Sea Street Beach, this 4BR, 2BA duplex (sleeps 10) is perfect for extended families or large groups. Have your own space, then gather together on the deck. Walk or drive to ice cream, dining, and more! Have a larger...

    Pets OK
    FREE CANCELLATION

    $176 to $418/night

  21. HOUSE
    63 Locust Rd Home at Orleans

    63 Locust Rd Home at Orleans

    Orleans, MA

    This 3BR/2BA Orleans home is within walking distance to virtually everything, including downtown Orleans, local restaurants, cafes, shops, parks, and art galleries. There’s also a convenient public transport service nearby. Feel like a day on the...

    FREE CANCELLATION

    $134 to $379/night

  22. HOUSE
    66 Indian Trail Home

    66 Indian Trail Home

    Chatham, MA

    Overlooking the saltwater inlet of Bucks Creek Marsh, this stunning 3BR/3BA waterfront home affords the quintessential Cape Cod experience. Vaulted ceilings with exposed beams and intriguing artwork create a sophisticated style, while large windows...

    FREE CANCELLATION

    $536 to $819/night

  23. 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
  24. 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

  25. HOUSE
    5 Redgate Lane Home

    5 Redgate Lane Home

    Falmouth, MA

    Inside the House Park up to 4 cars in the roomy driveway, then make your way up the stone walk to the front entrance. Step onto beautifully tiled floors and into the kitchen and sitting area. The sitting area has a sofa and 2 wicker armchairs, a...

    FREE CANCELLATION

    $194 to $617/night

  26. CONDOMINIUM
    26 Pleasant St Condo Unit 1

    26 Pleasant St Condo Unit 1

    Provincetown, MA

    Live in luxury at this 2BR/2BA Provincetown condo, with beautifully remodeled interiors, all new furnishings, and comfortable accommodations for four guests. Enjoy coastal breezes on your own private patio. The apartment is peacefully tucked away in...

    FREE CANCELLATION

    $305 to $589/night

  27. HOUSE
    Cape Cod Cottage on the Bay

    Cape Cod Cottage on the Bay

    East Falmouth, MA

    Feel the ocean breeze from this 3BR/1.5BA rustic beach home. Spacious and roomy, you and your guests can stretch out in the sun-dappled living room, the screened-in porch and even in the updated, oversized kitchen. Waquoit Bay's mild waters and...

    FREE CANCELLATION

    $138 to $428/night

  28. 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...

  29. HOUSE
    C409 Tricarico

    C409 Tricarico

    Charlestown, RI

    Bright and cheerful well maintained beach cottage with 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 moonlit...

  30. 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

    $624 to $691/night