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. 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

  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

    $158 to $449/night

  3. 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

  4. 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

  5. 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...

  6. 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
  7. 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

  8. 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

  9. 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...

  10. 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

  11. 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...

  12. 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 $418/night

  13. 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 $516/night

  14. 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...

  15. 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

  16. CONDOMINIUM
    Bentley Brook Studio

    Bentley Brook Studio

    Hancock, MA

    The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting...

    Pool Hot Tub

    $87 to $106/night

  17. CONDOMINIUM
    Bentley Brook 2 Bedroom

    Bentley Brook 2 Bedroom

    Hancock, MA

    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the...

    Pool Hot Tub

    $195 to $227/night

  18. 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

  19. HOUSE
    50 Sea Pine Road House

    50 Sea Pine Road House

    Wellfleet, MA

    This quaint 4BR/3BA is surrounded by tall trees and lush greenery. The Cape Cod Rail Trail (a 22-mile scenic path from Wellfleet to Dennis) is quite literally in your backyard. Just wander past the vegetable patch and hop on the trail! Enjoy a...

    FREE CANCELLATION

    $211 to $572/night

  20. HOUSE
    South Chatham Home 103

    South Chatham Home 103

    South Chatham, MA

    Bring the whole family to Cape Cod! This sprawling 4BR, 4.5BA home sleeps 10 in comfort. Kids will love the basement entertainment and sleep area, and you’ll adore the 3-season room. Walk to Forest Beach, and drive to downtown Chatham in 10...

    FREE CANCELLATION

    $211 to $866/night

  21. 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

  22. 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

  23. HOUSE
    C291 Reeb (1-Bedroom Home)

    C291 Reeb (1-Bedroom Home)

    Charlestown, RI

    Ocean views are captured by the sun-filled windows; waves lull you to sleep, miles of fabulous wide sandy beach steps from the front door. Bright, light and all refurbished in 09-new kitchen. Seafood dining "al fresco" around the corner... fishing,...

    $507 to $605/night

  24. HOUSE
    W531 Manente

    W531 Manente

    Charlestown, RI

    Large, well-appointed home within walking distance to the beach plus beach parking pass at Charlestown Town beach. Home has 4 bedrooms, one on the first floor, with master suite. It is located on a quiet road with pond views from second and third...

    $350 to $526/night

  25. HOUSE
    Quaint Cottage in the Woods

    Quaint Cottage in the Woods

    Wellfleet, MA

    The tranquil setting at this 4BR/3BA Cape Cod home will put you in full vacation mode. Set on 1.5 acres of land with soaring pine trees, the house is less than 10 minutes from beaches on the ocean and bay. Visit nearby Bound Brook Island Beach for...

    FREE CANCELLATION

    $258 to $668/night

  26. 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, renovated baths.New kitchen has granite counterops...

    $306 to $324/night

  27. HOUSE
    Chequessett Garden House

    Chequessett Garden House

    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 $433/night

  28. HOUSE
    90 Lieutenant Island Rd Home

    90 Lieutenant Island Rd Home

    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 $445/night

  29. HOUSE
    Cape Cod Beach Rental

    Cape Cod Beach Rental

    Wellfleet, MA

    Total relaxation and comfort in a house that feels like home, not a rental. Just a 3 min. walk to Wellfleet's Chipman's Cove, 6-12min. more to Indian Neck bay beach or a 25 min. nature walk around the cove and over famous Uncle Tim's Bridge to...

    Pets OK
    FREE CANCELLATION

    $237 to $609/night

  30. 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...

    $202 to $367/night