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 Oceanside- Scituate

    Colbyco Oceanside- Scituate

    Scituate, MA

    Spectacular Colonial where you wake up to the sound of the waves and unobstructed ocean views! Wake up to the sound of the waves as you take in the unobstructed ocean views! This spectacular newer (2013) colonial features the best in craftsmanship,...

  2. 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

  3. 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

  4. HOUSE
    90 Lieutenant Island Rd Home

    90 Lieutenant Island Rd Home

    Wellfleet, MA

    Property Overview  Nestled on 24 acres of Massachusetts Audubon and Wellfleet Conservation Trust Land, this brand-new 2BR/1.5 offers a sunroom, expansive balcony, and miles of lovely hiking trails. Spend sun-dappled afternoons in the enormous yard...

    FREE CANCELLATION

    $245 to $445/night

  5. HOUSE
    16 Alden St Home at Provincetown

    16 Alden St Home at Provincetown

    Provincetown, MA

    Property Overview  Tucked away off a quiet residential street in the center of Provincetown, this 4BR/3BA home offers a peaceful retreat along with a convenient location -- just steps away from the pier, ferry, and all the charming boutique shops...

    Pets OK
    FREE CANCELLATION

    $482 to $1042/night

  6. HOUSE
    Serene Chatham House by Oyster Pond

    Serene Chatham House by Oyster Pond

    Chatham, MA

    The far reaches of Cape Cod are easily discovered from this quaint 3BR, 2BA house hidden in the woods. Just steps from Oyster Pond, our rental sleeps 6 and will delight any kayaker or fisherman. Spend evenings listening to the birds on the porch - a...

    FREE CANCELLATION

    $121 to $510/night

  7. HOUSE
    Countryside House 21

    Countryside House 21

    Harwich, MA

    Property Overview  Surrounded by well-tended landscape and lush gardens, this two-story 4BR/2BA home offers the ultimate home base to explore the Cape’s tranquil countryside. Beautiful hardwood floors and coastal-inspired decor are sprinkled...

    Hot Tub
    FREE CANCELLATION

    $135 to $475/night

  8. HOUSE
    Chequessett Garden House

    Chequessett Garden House

    Wellfleet, MA

    Enjoy the peaceful surroundings of this 2BR/2BA cottage, less than a mile from the heart of Wellfleet. Those who love the great outdoors will be right at home in the artist’s garden. Indoors, high ceilings and natural light complement an...

    FREE CANCELLATION

    $186 to $433/night

  9. HOUSE
    Quaint Cottage in the Woods

    Quaint Cottage in the Woods

    Wellfleet, MA

    The tranquil setting at this 4BR/3BA Cape Cod home will put you in full vacation mode. Set on 1.5 acres of land with soaring pine trees, the house is less than 10 minutes from beaches on the ocean and bay. Visit nearby Bound Brook Island Beach for...

    FREE CANCELLATION

    $246 to $668/night

  10. HOUSE
    Woodsy Cape Cod Home

    Woodsy Cape Cod Home

    Wellfleet, MA

    Get in touch with the wildlife of Cape Cod at this 3BR, 2.5BA home (sleeps 8) just across from a tidal creek flowing into Cape Cod Bay. Travel the gorgeous trails of the Audubon Sanctuary, or drive 20 minutes to Provincetown. The marshes are...

    FREE CANCELLATION

    $121 to $534/night

  11. HOUSE
    75 Lake Home at Cotuit

    75 Lake Home at Cotuit

    Cotuit, MA

    A quintessential Cape Cod getaway awaits your crew of six at this newly remodeled 3BR/2BA Cotuit home. A cool color palette and coastal details set the scene for a memorable stay. Settle into the sectional sofa on the deck with your new vacation...

    FREE CANCELLATION

    $189 to $557/night

  12. HOUSE
    Cape Cod Home at Falmouth Harbor

    Cape Cod Home at Falmouth Harbor

    Falmouth, MA

    This charming 3BR/2BA Cape Cod home with room for 6 is just steps away from Falmouth Harbor. With new furnishings, a large deck, and an ideal location just a quarter-mile to the beach and a 15-minute walk to Main Street, all you need for a perfect...

    FREE CANCELLATION

    $115 to $545/night

  13. HOUSE
    41 Quivet Home at Dennis

    41 Quivet Home at Dennis

    Dennis, MA

    Classic New England charm awaits at this 4BR/2BA Dennis rental, with cedar shingles and a quaint nautical vibe. Spacious interiors and an expansive backyard offer lots of room for nine people to spread out. Throw a frisbee on the lush green lawn,...

    FREE CANCELLATION

    $385 to $705/night

  14. HOUSE
    312 Carriage Lane Home

    312 Carriage Lane Home

    Barnstable, MA

    With a quiet location in an historic Barnstable neighborhood, this 4 Bedroom / 2 Bathroom home offers a wonderful sense of seclusion, though countless local attractions sit right on your doorstep. Walk 1.2 miles to unique shops and restaurants...

    FREE CANCELLATION

    $162 to $571/night

  15. 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

    $158 to $587/night

  16. HOUSE
    6 Mockingbird Lane House

    6 Mockingbird Lane House

    Harwich, MA

    Look out over Buck's Pond from this 3BR/2BA Cape Cod house with water views from almost every room. Your own private beach is just steps away, where you can fish, swim, sail, or just stroll the sandy shore. This home is located in the idyllic family...

    FREE CANCELLATION

    $119 to $557/night

  17. HOUSE
    112 Ocean Drive Home

    112 Ocean Drive Home

    West Hyannis Port, MA

    Climb to the roof deck on the third floor of your 3BR/3.5BA classic Cape retreat for a peek at idyllic water views. Decorated in classic Cape Cod style, this newly constructed rental provides the comfort and nostalgia of a traditional beachside...

    FREE CANCELLATION

    $597 to $946/night

  18. HOUSE
    12 Bayberry Lane Home

    12 Bayberry Lane Home

    Eastham, MA

    Memorable beach trips begin at this elegant 2BR/3BA Eastham house. With a private master bedroom and separate family suite, there’s plenty of room to spread out. Watch the sun set over Cape Cod Bay from the upper deck, or follow the walking path...

    FREE CANCELLATION

    $829 to $1174/night

  19. HOUSE
    C222 Shafer (4-Bedroom Home)

    C222 Shafer (4-Bedroom Home)

    Charlestown, RI

    This spacious Colonial, located on a quiet dead end street, offers large, sun-filled rooms that are nicely furnished and ideal for a large group of up to 10 guests. Gather in the open kitchen/dining/family room or have quiet conversation in the den....

  20. HOUSE
    361 Shore House at North Truro

    361 Shore House at North Truro

    North Truro, MA

    Picturesque water views await at this 3BR/2BA Beach Point home just across the street from Cape Cod Bay. Make the quick walk to the beach or take a short drive to the stunning National Seashore beaches. Provincetown is just 2 miles away, offering...

    Pets OK
    FREE CANCELLATION

    $392 to $690/night

  21. HOUSE
    South Chatham Home 103

    South Chatham Home 103

    South Chatham, MA

    Bring the whole family to Cape Cod! This sprawling 4BR, 4.5BA home sleeps 10 in comfort. Kids will love the basement entertainment and sleep area, and you’ll adore the 3-season room. Walk to Forest Beach, and drive to downtown Chatham in 10...

    FREE CANCELLATION

    $255 to $865/night

  22. 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

    $164 to $475/night

  23. HOUSE
    22 Sunrise Lane Home

    22 Sunrise Lane Home

    Harwich, MA

    Completely renovated, this beautiful 4BR/2BA Harwich home features a welcoming open floor plan with high ceilings, hardwood floors, and central AC throughout. Whip up tasty dishes in the gourmet kitchen, relax in one of three living areas, or spend...

    FREE CANCELLATION

    $368 to $682/night

  24. HOUSE
    112 Ransom Home at Falmouth

    112 Ransom Home at Falmouth

    Falmouth, MA

    Sitting directly on Oyster Pond with a view of Vineyard Sound, tucked away on a private wooded peninsula, this 1930s summer home radiates charm and comfort with its own dock, two rowboats (with sails), a large canoe, and a kayak. Oyster Pond...

    Pets OK
    FREE CANCELLATION

    $476 to $680/night

  25. APARTMENT
    201 on Washington Apartment

    201 on Washington Apartment

    Jamaica Plain, Boston, MA

    The 201 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

    $220 to $466/night

  26. APARTMENT
    306 on Parker Hill Apartment

    306 on Parker Hill Apartment

    Boston, MA

    525 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

    $243 to $486/night

  27. 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

    $111 to $349/night

  28. HOUSE
    158 Long Beach Road Home

    158 Long Beach Road Home

    Centerville, MA

    Property Overview  Overlooking the Centerville River, this brand-new 3BR/1.5BA home affords an amazing location for your next Cape Cod getaway. Situated right on the water, an expansive deck provides a fantastic spot to relax, grill up dinner, and...

    FREE CANCELLATION

    $195 to $1057/night

  29. HOUSE
    Cape Cod Beach Rental

    Cape Cod Beach Rental

    Wellfleet, MA

    Total relaxation and comfort in a house that feels like home, not a rental. Just a 3 min. walk to Wellfleet's Chipman's Cove, 6-12min. more to Indian Neck bay beach or a 25 min. nature walk around the cove and over famous Uncle Tim's Bridge to...

    Pets OK
    FREE CANCELLATION

    $237 to $609/night

  30. HOUSE
    Coastal/Beach Access Cottage in Centerville

    Coastal/Beach Access Cottage in Centerville

    Barnstable, MA

    Historic grandeur, quaint seaside energy and a friendly community bring visitors from near and far to the shores of Cape Cod. This renovated 3-bedroom, 1-bath cottage embodies the best of this town by the sea, on a lakefront property in a tranquil...

    FREE CANCELLATION

    $217 to $556/night