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
    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 $404/night

  3. HOUSE
    Charming 4BR Cottage-- Steps to Long Pond

    Charming 4BR Cottage-- Steps to Long Pond

    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...

    FREE CANCELLATION

    $238 to $475/night

  4. HOUSE
    Updated 4BR Cape Cod, Steps to Beach

    Updated 4BR Cape Cod, Steps to Beach

    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

    $213 to $501/night

  5. HOUSE
    5BR on 3 Acres w/ Deck, Near Beaches

    5BR on 3 Acres w/ Deck, Near Beaches

    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

    $319 to $629/night

  6. DUPLEX
    Walk to Beach & Downtown! 6BR Duplex w/ Huge Yard

    Walk to Beach & Downtown! 6BR Duplex w/ Huge Yard

    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 $509/night

  7. DUPLEX
    3BR w/ Yard & Porch, Walk to Beach & Downtown!

    3BR w/ Yard & Porch, Walk to Beach & Downtown!

    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

  8. 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

  9. 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...

    $202/night

  10. 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

  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...

    $544/night

  12. 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...

    $232 to $300/night

  13. HOUSE
    Idyllic Mashpee 3BR on Lake

    Idyllic Mashpee 3BR on Lake

    Mashpee, MA

    Water, water everywhere you look at this fabulous 3BR/3.5BA lakefront home in scenic Mashpee, Cape Cod. Affectionately known as Point of View, this modern home is just a short drive (80-90 minutes) from downtown Boston and Providence and provides a...

    FREE CANCELLATION

    $440 to $782/night

  14. 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

    $220/night

  15. 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

  16. 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

  17. HOUSE
    Quiet 3BR – Walk to Old Silver Beach

    Quiet 3BR – Walk to Old Silver Beach

    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

  18. APARTMENT
    3399 Washington Unit 3

    3399 Washington Unit 3

    Jamaica Plain, Boston, MA

    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 unit washer/dryer! Unit...

    $112 to $366/night

  19. APARTMENT
    604 on Parker Hill

    604 on Parker Hill

    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

    $92 to $229/night

  20. 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 $332/night

  21. APARTMENT
    301 on Washington

    301 on Washington

    Jamaica Plain, Boston, MA

    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 heat, in unit...

    Pets OK

    $81 to $275/night

  22. APARTMENT
    206 on Parker Hill

    206 on Parker Hill

    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

    $112 to $229/night

  23. 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

    $87 to $229/night

  24. 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 $275/night

  25. CONDOMINIUM
    Sky View on Jones Hill

    Sky View on Jones Hill

    Boston, MA

    AMENITIES 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 Large bedrooms...

    Pets OK

    $93 to $295/night

  26. CONDOMINIUM
    Sawyer on Jones Hill

    Sawyer on Jones Hill

    Boston, MA

    Sawyer on Jones Hill 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....

    $99 to $343/night

  27. HOUSE
    Wooded Chatham Home on the Monomoy

    Wooded Chatham Home on the Monomoy

    Chatham, MA

    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 water. Large windows, cathedral ceilings, soft colors, and modern...

    Hot Tub
    FREE CANCELLATION

    $275 to $497/night

  28. 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

    $294 to $592/night

  29. 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

    $314 to $367/night

  30. DUPLEX
    Spacious 4BR Close to Sea Street Beach

    Spacious 4BR Close to Sea Street 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...

    FREE CANCELLATION

    $213 to $439/night