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 Murphys House

    Colbyco Murphys House

    Scituate, MA

    South Shore Beach Vacation in Quaint New England Fishing Village Experience the sound of crashing waves and smell of the ocean along with a sweeping vista of the sea and lighthouses in this 1925 cobblestone exterior, newly redecorated, luxury...

    $754 to $986/night

  2. HOUSE
    C323 Kahn (3-Bedroom Home)

    C323 Kahn (3-Bedroom Home)

    Charlestown, RI

    Privacy by the beach…this spacious, comfortable 3 bedroom, 4 bath home sleeps 10. There is a fourth room over the garage which is a great sleeping area for the kids and their friends. There are many areas to hang out with friends and family or...

    $300 to $422/night

  3. HOUSE
    C021 Howard (3-Bedroom Home)

    C021 Howard (3-Bedroom Home)

    Charlestown, RI

    Charlestown Ocean Ridge South. This comfortable home is yours to enjoy on your vacation. It has an open living, dining and kitchen areas. There are three nice sized bedrooms, the master bedroom with it's own bath and two additional bedrooms with a...

  4. HOUSE
    C197 Perry (3-Bedroom Home)

    C197 Perry (3-Bedroom Home)

    Charlestown, RI

    Just a short walk to Charlestown Beach from this 3 bedroom, 2 bath Cottage. Distance to the Charlestown Beach is approximately 0.25 miles and a really short walk to Charlestown Pond. Outside shower has hot and cold water. Charlestown is a town of...

    $232 to $300/night

  5. 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 $246/night

  6. 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 $556/night

  7. HOUSE
    C389 Lorenzo

    C389 Lorenzo

    Charlestown, RI

    Enjoy panoramic views of Charlestown Beach and Ninigret Pond from the upstairs level of this well cared for home! The large open space and vaulted ceiling on this floor make up the well equipped kitchen, dining, living room and half bath. Lots of...

  8. HOUSE
    C164 Colby (3-Bedroom Home)

    C164 Colby (3-Bedroom Home)

    Charlestown, RI

    Bring your boat ( up to 19ft) and keep it at the dock in front of this peaceful 1960's cottage on Ningret Pond-( direct access to the Ocean). Ranch in private wooded setting on cul-de sac with wonderful water views of salt pond from kitchen/ living...

    $196 to $300/night

  9. HOUSE
    C413 Alper (2-Bedroom Home)

    C413 Alper (2-Bedroom Home)

    Charlestown, RI

    This delightful home is located just a short walk to Green Hill Pond and 1.5 miles to Charlestown Town Beach. With two lovingly furnished bedrooms, one with full master bath and a full bath with laundry to accommodate the second bedroom, spacious...

    Pets OK

    $183 to $220/night

  10. 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

  11. HOUSE
    C403 Orsini (4-Bedroom Home)

    C403 Orsini (4-Bedroom Home)

    Charlestown, RI

    Make your summer memories here at this well maintained home in Charlestown! Located roughly 1/2 mile from Charlestown Beach it has sleeping for 10 guests. There are two levels each with it's own kitchen,living,dining space which is ideal for two...

    $245 to $367/night

  12. HOUSE
    C402 Willow (2-Bedroom Home)

    C402 Willow (2-Bedroom Home)

    Charlestown, RI

    Lasting summer time memories are made here in this comfortable 2 bed room, 1.5 bth. An over-sized deck located on the south side of the house is large enough to grill and dine out on. A Charlestown town beach pass is provided . This pass allows you...

    $116 to $220/night

  13. HOUSE
    49 Brooks Home at Harwich Port

    49 Brooks Home at Harwich Port

    Harwich Port, MA

    This spacious 4BR/2.5BA Cape Cod home is just a five-minute walk from the beach. After a day in the sun, unwind in the shady backyard. Throw a BBQ or just relax in the hammock. Nautical décor and multiple living spaces, including three living rooms...

    FREE CANCELLATION

    $354 to $791/night

  14. APARTMENT
    301 on Washington Apartment

    301 on Washington Apartment

    Jamaica Plain, Boston, MA

    All New for 2017! Wonderfully built brand new 990sq foot 2 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...

    Pets OK

    $81 to $276/night

  15. CONDOMINIUM
    Dorset at Upham's Corner

    Dorset at Upham's Corner

    Boston, MA

    AMENITIES Minutes to the South End - Walk to Castle Beach - Easy & Free Parking Fully furnished 1200sf luxury apartment centrally located in Boston near the historic South End 3 Bedrooms/1 Bathroom All beds are queen sized Full Kitchen Free Wifi...

    Pets OK

    $93 to $343/night

  16. DUPLEX
    Dennisport Duplex by the Beach

    Dennisport Duplex by the Beach

    Dennis Port, MA

    Look no further, you’ve found the perfect Dennisport vacation rental! This delightful duplex is only an 8-minute walk from popular Sea Street Beach, and just a short stroll to ice cream, dining, and more. Sleeps 8. The 4BR/2BA duplex is comprised...

    FREE CANCELLATION

    $217 to $439/night

  17. HOUSE
    Walkable Falmouth Hts Beach Home

    Walkable Falmouth Hts Beach Home

    Falmouth, MA

    Bring the whole gang for a quintessential Cape Cod getaway at this adorable and spacious 5BR, 1.5BA (sleeps 10) bungalow. Park your car and leave it—you’re within walking distance of Falmouth Heights Beach, ferry to Martha’s Vineyard and Cape...

    Pets OK
    FREE CANCELLATION

    $299 to $592/night

  18. HOUSE
    Wooded Chatham Home on the Monomoy

    Wooded Chatham Home on the Monomoy

    Chatham, MA

    Wooded 3BR, 2BA Chatham Home on the Monomoy with Hot Tub & Kayak Launch This peaceful 3BR, 2BA woodland Chatham home (sleeps 6) is located right on the Monomoy River. Patio doors open to the travertine stone terrace, where a hot tub overlooks the...

    Hot Tub
    FREE CANCELLATION

    $275 to $513/night

  19. APARTMENT
    304 on Washington Apartment

    304 on Washington Apartment

    Jamaica Plain, Boston, MA

    The 304 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, full kitchen including dishwasher, disposal,...

    Pets OK

    $81 to $276/night

  20. CONDOMINIUM
    Alameda 2 at Weld Farm

    Alameda 2 at Weld Farm

    West Roxbury, MA

    Our Alameda 2 property in Boston features a vintage 1920’s floor plan and tall ceilings. The unit offers 2.5 bedrooms and an additional study for your comfort. The Alameda 2 hosts a large living room, dining room and renovated eat in...

    Pets OK

    $86 to $230/night

  21. HOUSE
    8 Peck's Way Orleans Home

    8 Peck's Way Orleans Home

    Orleans, MA

    Kayakers and nature lovers take note! This 4BR, 2BA (sleeps 8) house sits on 7+ waterfront acres in Orleans, offering extraordinary privacy with exquisite water views of historic Arey's Pond, part of Pleasant Bay. Note: this is a salt water pond....

    FREE CANCELLATION

    $299 to $476/night

  22. 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

  23. 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

  24. HOUSE
    46 Paola Dr Home at East Falmouth

    46 Paola Dr Home at East Falmouth

    East Falmouth, MA

    Picturesque views of Bournes Pond await from this quaint 4BR/2BA East Falmouth home. Enjoy a great location just minutes from downtown Falmouth and the Martha's Vineyard ferry and surrounded by opportunities to paddle board, fish, clam, and kayak....

    Pets OK
    FREE CANCELLATION

    $243 to $461/night

  25. 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

  26. HOUSE
    181 Chase Home at Hyannis

    181 Chase Home at Hyannis

    Hyannis, MA

    Property Overview  Unparalleled charm and craftsmanship await at this 3BR/2BA single-story home. Originally built in 1937, your Cape Cod getaway boasts classic features including hardwood floors, arched doorways, gorgeous beam ceilings, and a...

    FREE CANCELLATION

    $205 to $416/night

  27. HOUSE
    3BR on Private Half-Acre, Near Beach

    3BR on Private Half-Acre, Near Beach

    Harwich, MA

    Situated on the desirable Harwich/Chatham line, this charming 3BR/3BA home affords a prime locale on a quiet street just off Route 28. Spanning three floors, your spacious retreat sits on a private half-acre of land and includes a beautifully...

    FREE CANCELLATION

    $238 to $446/night

  28. 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

  29. 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

  30. COTTAGE
    Small Cottage | Woods Hole

    Small Cottage | Woods Hole

    Woods Hole, MA

    Follow the dirt road to our 2BR (sleeps 4) cottage by the sea. With charming yet modernized character as well as a private beach plus access to the Shining Sea Bikeway, our rental offers you the chance to truly explore Cape Cod. Walk or bike to...

    FREE CANCELLATION

    $337 to $656/night