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
    Delightful West Harwich House

    Delightful West Harwich House

    West Harwich, MA

    This charming 3BR/2BA 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 -- this rental also...

    FREE CANCELLATION

    $318 to $437/night

  2. HOUSE
    87 West Pond Rd Home

    87 West Pond Rd Home

    Chatham, MA

    Property Overview Nestled in a quaint Cape Cod enclave, this 3BR/2BA home is less than one mile to pristine Goose Pond, a local favorite for swimming, canoeing, and kayaking. Enjoy bike paths, hiking trails, and Volunteer Park - all within walking...

    FREE CANCELLATION

    $238 to $492/night

  3. 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 $457/night

  4. 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

    $225 to $403/night

  5. 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 $517/night

  6. 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 $929/night

  7. 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

    $1,225 to $2,145/night

  8. 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

    $217 to $471/night

  9. 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

    $262 to $537/night

  10. 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

    $196 to $436/night

  11. 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 $403/night

  12. 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

    $199 to $463/night

  13. 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 $771/night

  14. COTTAGE
    C396 Schroeder

    C396 Schroeder

    Charlestown, RI

    Beach: West Beach *Classic Rhode Island beach cottage with full view of the ocean & Block Island * Located on private West Beach in Charlestown, RI *Rental comes with beach privileges * Porches on three sides for both shade and sun relaxing...

    Pets OK

    $202 to $458/night

  15. 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

    $238 to $475/night

  16. HOUSE
    11 Spartina Place Home

    11 Spartina Place Home

    Falmouth, MA

    Plan the ultimate beach vacation at this 3BR/3BA (plus bonus sleeping space) retreat in the Old Silver Beach neighborhood of West Falmouth. The house comes stocked with beach chairs and gear, so it’s simple to make the quick walk to the bayside....

    FREE CANCELLATION

    $386 to $528/night

  17. HOUSE
    349 Old Kings Highway Home

    349 Old Kings Highway Home

    Wellfleet, MA

    You'll love spending your time outdoors at this large 5BR/2BA Wellfleet home, located on three wooded acres with a 50’ wraparound deck. Fire up the grill for an afternoon barbeque and enjoy views of the vernal pools and wildlife. Pack for the...

    Pets OK
    FREE CANCELLATION

    $314 to $676/night

  18. 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

    $211 to $241/night

  19. 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

    $422 to $528/night

  20. CONDOMINIUM
    Charming Cape Townhouse

    Charming Cape Townhouse

    Brewster, MA

    This charming 2-bedroom, 2-bath plus a loft townhouse promises a fantastic stay on the Cape! Newly renovated and filled with natural light, this rental features warm wood floors and modern marble-touched bathrooms. Brewster is famous for its...

    FREE CANCELLATION

    $319 to $346/night

  21. HOUSE
    40 Major Doane Rd Home

    40 Major Doane Rd Home

    Wellfleet, MA

    Welcome to this ideal 5BR/2.5BA Wellfleet getaway in a quiet, residential cul-de-sac less than 2 miles from the town pier and Cahoon Hollow Beach on the Cape Cod National Seashore. With three decks for breathing in the salty sea air, three levels of...

    FREE CANCELLATION

    $251 to $580/night

  22. HOUSE
    40 Epanow Home at Eastham

    40 Epanow Home at Eastham

    Eastham, MA

    Property Overview Featuring miles of unspoiled shoreline and warmer bay beaches, Eastham is a sure bet for your next Cape Cod getaway. An ideal place to relax, this two-story 5BR/2.5BA home offers 2,274 square feet of comfortable living space --...

    FREE CANCELLATION

    $392 to $714/night

  23. HOUSE
    43 Santuit Ln Home at Mashpee

    43 Santuit Ln Home at Mashpee

    Mashpee, MA

    This four-season vacation home is designed for comfort and family fun. In warm weather, pick up fresh lobster for your crew, and enjoy a seafood feast on the deck overlooking the lake. During chilly months, reconnect with loved ones in the spacious...

    FREE CANCELLATION

    $440 to $782/night

  24. COTTAGE
    63 Pickerel Cove Circle Cottage

    63 Pickerel Cove Circle Cottage

    Mashpee, MA

    Property Overview  Tucked away in a charming Cape Cod neighborhood, this classic 2BR cottage sits on the lovely Mashpee-Wakeby Pond, which is the largest pond on the Cape and has phenomenal Bass fishing (contests are held here). It is also a...

    FREE CANCELLATION

    $168 to $295/night

  25. HOUSE
    200 Shurtleff Rd Home

    200 Shurtleff Rd Home

    Eastham, MA

    Situated less than 50 yards from a private Association Beach on Cape Cod Bay, this 3BR/2BA Eastham home is perfect for the relaxed coastal vacation you’ve been dreaming about. Enjoy lazing on the sand, swimming in the waters, and strolling along...

    FREE CANCELLATION

    $330 to $669/night

  26. 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

    $231 to $507/night

  27. 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

    $260 to $408/night

  28. HOUSE
    63 Harbor Road House

    63 Harbor Road House

    Hyannis, MA

    This spacious 4BR/3BA classic Cape Cod abode is located just a 3-minute walk from a private beach. Enjoy quality time with friends and family in three inviting living spaces, or savor al fresco meals on the patio in the big fenced yard. Spend...

    FREE CANCELLATION

    $274 to $686/night

  29. HOUSE
    120 Boreen Home at Eastham

    120 Boreen Home at Eastham

    Eastham, MA

    Situated on a forested property in the highly desirable Dunes Beach Association, your 4BR getaway offers a serene location between the woods and sea. Follow a sandy pathway to enjoy direct access to a glorious semi-private Cape Cod beach. This newly...

    FREE CANCELLATION

    $275 to $571/night

  30. 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

    $869 to $1,061/night