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
    216 Pimlico Pond Road Home

    216 Pimlico Pond Road Home

    Mashpee, MA

    Property Overview Mashpee Heaven provides rare access to one of Cape Cod's largest freshwater lakes. Enjoy swimming from a private pier and exploring the lake’s three islands, two beaches, and miles of trails. Centrally located, the 3BR/2BA...

    FREE CANCELLATION

    $187 to $436/night

  2. 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

  3. 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

    $268 to $487/night

  4. 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

    $226 to $466/night

  5. 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

    $181 to $403/night

  6. 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

    $180 to $369/night

  7. 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 $532/night

  8. 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

    $151 to $367/night

  9. HOUSE
    3BR “Perfect Moments” on Swan Pond

    3BR “Perfect Moments” on Swan Pond

    Dennis Port, MA

    Situated on Swan Pond, this newly remodeled home enjoys the privacy of a wooded lot and includes a large deck and an outdoor shower. Launch your own kayak from the backyard during high tide, and enjoy some of the best paddling on the Cape. When...

    FREE CANCELLATION

    $256 to $417/night

  10. 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...

  11. 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...

  12. HOUSE
    5 Third Home in Harwich

    5 Third Home in Harwich

    Harwich, MA

    Your 3BR/2BA is just a block away from Long Pond—swim, float, splash, paddle, and sail on Cape Cod’s largest lake, named one of the best swimming spots by Boston Magazine. Hop on your bikes and ride the 25-mile Rail Trail that runs from Dennis...

    FREE CANCELLATION

    $263 to $466/night

  13. HOUSE
    803 Commercial St Home

    803 Commercial St Home

    Provincetown, MA

    Plan a beachfront getaway for twelve guests at this 5BR/3BA home, where generous picture windows afford water views from almost every room. Spend leisurely vacation days on the two-story patio overlooking Cape Cod Bay. With lounge seating, a gas...

    Pool Pets OK
    FREE CANCELLATION

    $1,168 to $2,108/night

  14. 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

    $175 to $457/night

  15. CONDOMINIUM
    Coastline Cheer in Provincetown

    Coastline Cheer in Provincetown

    Provincetown, MA

    Teeming with coastal cheer, this bright 3BR/2.5BA condo is the quintessential Cape Cod vacation rental. Sweeping ocean vistas, seashore hues, and a location in the heart of the historic west end allow you to truly experience the charm and beauty of...

    FREE CANCELLATION

    $279 to $679/night

  16. HOUSE
    16 East Falmouth Home

    16 East Falmouth Home

    East Falmouth, MA

    Set on a scenic 4-acre plot, this historic (newly renovated) 5BR + bonus room, 2BA East Falmouth home is nestled on Bourne Pond. Kayak out on the water, relax between private decks and indoor sitting areas, and drive 5-10 min to dining/beaches....

    FREE CANCELLATION

    $292 to $577/night

  17. 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

    $533 to $893/night

  18. 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

    $164 to $398/night

  19. 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

  20. 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

  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
    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

  23. HOUSE
    C289 Boullianne

    C289 Boullianne

    Charlestown, RI

    Walk, bike or drive ? 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

  24. 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 $587/night

  25. 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

  26. 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

    $192 to $459/night

  27. 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

    $418 to $761/night

  28. 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

    $231 to $537/night

  29. 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 $522/night