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
    C222 Shafer (4-Bedroom Home)

    C222 Shafer (4-Bedroom Home)

    Charlestown, RI

    This spacious Colonial, located on a quiet dead end street, offers large, sun-filled rooms that are nicely furnished and ideal for a large group of up to 10 guests. Gather in the open kitchen/dining/family room or have quiet conversation in the den....

    $440/night

  2. HOUSE
    4BR w/ Private Beach Access

    4BR w/ Private Beach Access

    Eastham, MA

    Situated on a forested property in the highly desirable Dunes Beach Association, your 4BR getaway offers a serene location between the woods and sea. Follow a sandy pathway to enjoy direct access to a glorious semi-private Cape Cod beach. This...

    FREE CANCELLATION

    $193 to $568/night

  3. HOUSE
    W091 Vaccaro

    W091 Vaccaro

    Charlestown, RI

    We welcome you to enjoy our family cottage nestled in the woods and just a 10 minutes from the beach. Our place has a large backyard with plenty of shade and privacy. Take advantage of our deck and patio on our one acre lot. Feel free to gather...

    $134 to $210/night

  4. HOUSE
    New 2BR on Nature Conserve w/ Sun Deck

    New 2BR on Nature Conserve w/ Sun Deck

    Wellfleet, MA

    PROPERTY OVERVIEW Nestled on 24 acres of Massachusetts Audubon and Wellfleet Conservation Trust Land, this brand-new 2BR/1.5 offers a sunroom, expansive balcony, and miles of lovely hiking trails. Spend sun-dappled afternoons in the enormous yard...

    FREE CANCELLATION

    $211 to $378/night

  5. HOUSE
    2BR Garden Cottage, Near Beach

    2BR Garden Cottage, Near Beach

    Wellfleet, MA

    Enjoy the peaceful surroundings of this 2BR/2BA cottage, less than a mile from the heart of Wellfleet. Those who love the great outdoors will be right at home in the artist’s garden. Indoors, high ceilings and natural light complement an...

    FREE CANCELLATION

    $158 to $372/night

  6. HOUSE
    Big 4BR Gem w/ Fenced Yard & Private Beach Access

    Big 4BR Gem w/ Fenced Yard & Private Beach Access

    Hyannis, MA

    This spacious 4BR/2.5BA classic Cape Cod abode is located just a 3-minute walk from a private beach. Enjoy quality time with friends and family in three inviting living spaces, or savor alfresco meals on the patio in the big fenced yard. Spend...

    FREE CANCELLATION

    $261 to $653/night

  7. HOUSE
    Remodeled 4BR Near Beaches & Golf

    Remodeled 4BR Near Beaches & Golf

    Dennis, MA

    Classic New England charm awaits at this 4BR/2BA Dennis rental, with cedar shingles and a quaint nautical vibe. Spacious interiors and an expansive backyard offer lots of room for nine people to spread out. Throw a frisbee on the lush green lawn,...

    FREE CANCELLATION

    $405 to $603/night

  8. DUPLEX
    3BR w/ Yard & Outdoor Shower- Walk Everywhere!

    3BR w/ Yard & Outdoor Shower- Walk Everywhere!

    Dennis Port, MA

    This single-story 3BR cottage is a quaint getaway offering superb outdoor space. Relax on the front porch and host a fun cookout in the large backyard. An outdoor shower is great for rinsing sandy toes after a fun beach day. Walk across the street...

    FREE CANCELLATION

    $211 to $241/night

  9. HOUSE
    C315 Broccoli 676

    C315 Broccoli 676

    Charlestown, RI

    Ocean front on Charlestown Beach. Make a lifetime of memories at this newly built beach house. Relax on the deck overlooking the Atlantic Ocean, Block Island, the Breachway and miles of one of South County’s most sought after beaches. Enjoy your...

    $581 to $844/night

  10. HOUSE
    C384 Buckley

    C384 Buckley

    Charlestown, RI

    Begin making those vacation memories in this seaside cottage . Nicely furnished , this one level home has open kitchen & living area , large deck and an outside shower to rinse off that beach sand . Sleeping accommodations for 6 . Master bedroom has...

    $293 to $324/night

  11. HOUSE
    C368 Dudek (3-Bedroom Home)

    C368 Dudek (3-Bedroom Home)

    Charlestown, RI

    Beach Pass to Blue Shutters and Charlestown Town Beach. Charming and spacious three bedroom Cape with central air and nice hardwood floors thru out. Large spacious bright living room with wall of atrium doors and windows that welcomes in the gardens...

    $183 to $330/night

  12. HOUSE
    C359 Matos (5-Bedroom Home)

    C359 Matos (5-Bedroom Home)

    Charlestown, RI

    This 5 bedroom, 2 bath gem has room for the whole family to vacation in comfort. A recent interior renovation offers updates everywhere. An extra large deck overlooking the acre of back yard lends itself to summer fun and entertaining. New outside...

    $263 to $458/night

  13. HOUSE
    C047 Sol (2-Bedroom Home)

    C047 Sol (2-Bedroom Home)

    Charlestown, RI

    Charlestown Beach. Sit on the deck and enjoy the beautiful views of the ocean and Block Island. There are no houses in front of you to block the views. There is a private walkway across the sand dune that takes you to the beach where you can jump...

    $367 to $489/night

  14. HOUSE
    C024 Broccoli

    C024 Broccoli

    Charlestown, RI

    This two story cottage offers tons of sleeping and generous sized rooms. Fresh, immaculate and cute. Large dining/sun bathing deck. 1 acre of yard, shed for the bikes. .75 of a mile to beach, 1/4 mile to ice cream, bakery & deli shops. "Sea Breeze...

    $318 to $440/night

  15. HOUSE
    Remodeled 3BR, Walk to Cotuit Village

    Remodeled 3BR, Walk to Cotuit Village

    Cotuit, MA

    A quintessential Cape Cod getaway awaits your crew of eight at this newly remodeled 3BR/2BA Cotuit home. A cool color palette and coastal details set the scene for a memorable stay. Settle into the sectional sofa on the deck with your new vacation...

    FREE CANCELLATION

    $229 to $549/night

  16. HOUSE
    C129 Albert (3-Bedroom Home)

    C129 Albert (3-Bedroom Home)

    Charlestown, RI

    A Vacation spot where memories are made! Come and enjoy family time at this spacious 1700 SQFT home by the beach. The house is newly remodeled; features hardwood flooring, newly carpeted bedrooms, and renovated baths, new kitchen that has granite...

    $306 to $324/night

  17. 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

  18. 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

  19. 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

  20. 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

  21. 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

  22. 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

  23. 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

  24. 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

    $219 to $629/night

  25. 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

  26. 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

  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

    $189 to $404/night

  28. 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

  29. 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

    $322 to $528/night

  30. HOUSE
    C354 Munier (2-Bedroom Home)

    C354 Munier (2-Bedroom Home)

    Charlestown, RI

    Close to the beach - less than a mile - with an association beach parking pass and plenty of room. This house has window air conditioners and internet access. There is an amazing and very private back yard with deck and large, enclosed outdoor...

    $202 to $293/night