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
    Carpe Diem at Nantucket Retreats

    Carpe Diem at Nantucket Retreats

    Nantucket, MA

    Overlook the moors of Forever Wild Sanctuary and Polpis Harbor from Carpe DiemNew for 2019 - Pool and fire pit! The photos in the photo gallery of the pool and fire pit are included only to show what the finished product will look like. These few...

    Pool Hot Tub

    $2,686 to $5,204/night

  2. HOUSE
    SeaWatch

    SeaWatch

    Nantucket, MA

    SeaWatch is an oceanfront dream in Quidnet Treat your group to a captain's view of the Atlantic Ocean and Sesachacha Pond at SeaWatch, an exceptional vacation rental at the edge of the ocean complete with beach access and a separate guest house....

    $1,511 to $3,189/night

  3. HOUSE
    C382 Linehan

    C382 Linehan

    Charlestown, RI

    Enjoy plenty of open living space in this reverse living beach home with pretty views of Ninigret Pond. This 4 bedroom, 2 bath home will comfortably sleep 7 people. The upper floor living area offers an open living room, kitchen and dining area with...

  4. 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

  5. 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

    $238 to $717/night

  6. 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

    $161 to $461/night

  7. 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

    $249 to $498/night

  8. 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

    $228 to $622/night

  9. 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

    $221 to $480/night

  10. 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

    $214 to $433/night

  11. 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

    $209 to $382/night

  12. 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

    $158 to $534/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

    $166 to $744/night

  14. 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

    $224 to $912/night

  15. 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

    $255 to $733/night

  16. 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

    $306 to $420/night

  17. 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

    $224 to $485/night

  18. 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

    $232 to $384/night

  19. 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...

    $183 to $220/night

  20. 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

    $208 to $451/night

  21. 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

    $137 to $561/night

  22. APARTMENT
    3399 Washington Unit 3

    3399 Washington Unit 3

    Jamaica Plain, Boston, MA

    All New for March 2018! Wonderfully built brand new 3 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 heat, in...

    FREE CANCELLATION

    $238 to $489/night

  23. 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 $260/night

  24. HOUSE
    C417 Nutmeg Lane

    C417 Nutmeg Lane

    Charlestown, RI

    Amenities:Allow PetsBeach Location Type - Walk to BeachBedding 2 - QueenBlenderDining Seats - 6Distance to Beach - 0.5-1 mi.Full KitchenLobster PotNearby Grocery StoreNearby MedicalNearby PlaygroundNumber of Bathrooms - 1Stove -...

    Pets OK
  25. 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...

  26. 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. There is a double sleep sofa in the family room/den for extra sleeping space. Distance to the Charlestown Beach is approximately 0.25 miles and a really short walk to...

    $232 to $300/night

  27. 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

  28. 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

  29. 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

  30. HOUSE
    C365 Willinsky

    C365 Willinsky

    Charlestown, RI

    Beach: Charlestown Beach Charlestown By The Sea. This home offers the perfect retreat after a day at the beach or sightseeing. A light and airy contemporary it has central air, spacious bedrooms. It is clean, bright and nicely appointed on quiet...