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
    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

  2. 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 $459/night

  3. HOUSE
    265 Main Street House

    265 Main Street House

    Wellfleet, MA

    Gaze out at the charms of downtown Wellfleet from your second-floor balcony in this 4BR/3BA home. Restaurants, shops, and the coastal town’s famous galleries are just steps away. Head down Main Street towards the Town Pier, Mayo Beach, and...

    FREE CANCELLATION

    $244 to $928/night

  4. 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

    $173 to $325/night

  5. HOUSE
    149 Uncle Venies Road Home

    149 Uncle Venies Road Home

    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 208. Spanning three floors, your spacious retreat sits on a private half-acre of land and includes a beautifully...

    FREE CANCELLATION

    $238 to $495/night

  6. HOUSE
    23 Shore Road Extension Home

    23 Shore Road Extension Home

    West Harwich, MA

    From the moment you walk up the stone path, you’ll be charmed by this classic 4BR/3BA Cape Cod home. With two living areas and a large outdoor space, this spot easily fits two families or groups of up to eight guests. Located on a quiet lane,...

    Pets OK
    FREE CANCELLATION

    $185 to $573/night

  7. 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

    $185 to $424/night

  8. 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

    $106 to $271/night

  9. 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

  10. 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...

  11. 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...

  12. 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

  13. 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

  14. 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

  15. 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

  16. 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

  17. 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
    FREE CANCELLATION

    $253 to $381/night

  18. 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
    FREE CANCELLATION

    $290 to $455/night

  19. 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
    FREE CANCELLATION

    $306 to $490/night

  20. APARTMENT
    206 on Parker Hill Apartment

    206 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

    $264 to $390/night

  21. APARTMENT
    604 on Parker Hill Apartment

    604 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 $390/night

  22. CONDOMINIUM
    Dorset at Upham's Corner

    Dorset at Upham's Corner

    Boston, MA

    Property DescriptionMinutes to the South End - Walk to Castle Beach - Easy & Free Parking Fully furnished 1200 square foot luxury apartment centrally located in Boston near the historic South End 3 Bedrooms/1 Bathroom All beds are queen sized...

    Pets OK
    FREE CANCELLATION

    $269 to $402/night

  23. CONDOMINIUM
    Sawyer on Jones Hill

    Sawyer on Jones Hill

    Boston, MA

    Savin Hill - UMass Boston - Minutes from South End The Sawyer is what most travelers wish to find and rarely do. The Sawyer is walking distance to the subway for a direct line into downtown and the historic district of Boston. This unit is a...

    FREE CANCELLATION

    $294 to $454/night

  24. CONDOMINIUM
    Sky View on Jones Hill

    Sky View on Jones Hill

    Boston, MA

    Property Description Easy Walk to the Subway Convenient Off-street Parking for 2 cars with plentiful and free on-street parking near the residence. No meters to feed and no parking garage to pay! Breathtaking Panoramic views of Downtown Boston 2...

    Pets OK
    FREE CANCELLATION

    $281 to $437/night

  25. 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

    $266 to $507/night

  26. 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

    $398 to $554/night

  27. 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

    $211 to $613/night

  28. HOUSE
    Cape Cod Home in the Trees

    Cape Cod Home in the Trees

    Eastham, MA

    Have a classic American beach trip at this 4-bed, 2-bath Eastham Cape Cod style house with room for 8. With a charming wood-burning fireplace, huge back deck, horseshoe toss, and a great location within biking distance to the beach, your group will...

    FREE CANCELLATION

    $318 to $429/night

  29. CONDOMINIUM
    Cape Townhouse Unit 11

    Cape Townhouse Unit 11

    Brewster, MA

    ThisThis 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

    $314 to $426/night

  30. 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

    $275 to $749/night