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
    A Healing Home in Cape Cod

    A Healing Home in Cape Cod

    Centerville , MA

    An owner-occupied, private home decorated with lush gardens and nature trails. Great for family getaways. Lounge on the sun deck with summer time snacks for the perfect tan, or have a late night fireside chat while roasting marshmallows: enjoy a cup...

    FREE CANCELLATION

    $156 to $273/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....

    $1511 to $3189/night

  3. 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

  4. 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

    $2686 to $5204/night

  5. 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

  6. 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

  7. 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

    $222 to $471/night

  8. 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

    $217 to $493/night

  9. 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

    $225 to $479/night

  10. 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

  11. 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

  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. 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...

  14. 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

  15. 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

  16. 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

  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

    $215 to $382/night

  18. 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

    $255 to $521/night

  19. 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

  20. 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

  21. 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

    $190 to $449/night

  22. 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

    $375 to $554/night

  23. 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

    $231 to $806/night

  24. 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

    $243 to $474/night

  25. 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

  26. 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

    $162 to $319/night

  27. 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

    $221 to $484/night

  28. APARTMENT
    C400 Caswell

    C400 Caswell

    Charlestown, RI

    Beach: Blue Shutters Beach: Blue Shutters Beach, East Beach, Charlestown Beach, Ninigret Pond, Burlingame State Park/Watchaug Pond COMES WITH BEACH PASS TO BLUE SHUTTERS BEACH AND CHARLESTOWN BEACH Our place has a large backyard with plenty of...

  29. HOUSE
    C021 Howard (3-Bedroom Home)

    C021 Howard (3-Bedroom Home)

    Charlestown, RI

    Neighborhood: Charlestown Beach: Charlestown Beach 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 its own bath and two...

  30. 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...