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
    32 Crosby Lane House

    32 Crosby Lane House

    Falmouth, MA

    Perched on a hill overlooking the tidal Moonakis River, Osprey Point is a 3BR/2.5BA remodeled builder’s home offering a peaceful retreat for six. With three living areas and a sprawling backyard, there’s plenty of room to gather and have fun....

    FREE CANCELLATION

    $418 to $761/night

  2. HOUSE
    35 Timberlane Drive Home

    35 Timberlane Drive Home

    Mashpee, MA

    Nestled right on Santuit Pond, this charming 3BR/3BA home is the perfect Cape Cod getaway for a family or group of friends. Stairs lead down to a private floating dock where you can launch the provided kayaks. Rent jet skis or sailboats for even...

    FREE CANCELLATION

    $226 to $466/night

  3. HOUSE
    Eastham Gem Home 190

    Eastham Gem Home 190

    Eastham, MA

    Property Overview  This welcoming 4BR/1.5BA cottage in Eastham offers the ultimate coastal getaway. Supremely located between the tranquil bay-side beaches and invigorating dunes and ocean waves of Nauset Light Beach, this home has it all,...

    FREE CANCELLATION

    $268 to $487/night

  4. 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
  5. HOUSE
    Colbyco Oceanside- Scituate

    Colbyco Oceanside- Scituate

    Scituate, MA

    Spectacular Colonial where you wake up to the sound of the waves and unobstructed ocean views! Wake up to the sound of the waves as you take in the unobstructed ocean views! This spectacular newer (2013) colonial features the best in craftsmanship,...

    $696 to $986/night

  6. HOUSE
    Colbyco Veira Park- Martha's Vineyard

    Colbyco Veira Park- Martha's Vineyard

    Martha's Vineyard, MA

    Located in the Oaks Bluff section of Martha's Vineyard, our single family home was Built in 1870, and renovated in 1973, and then again in 2017. The home is approximately 1,700 Sq. Ft., and there are three entryways.  Walk to beach, town (Circuit...

    $580 to $812/night

  7. HOUSE
    Colbyco CitySide

    Colbyco CitySide

    Boston, MA

    Rare large and comfortable Boston single family home available for vacation or short term rental. It is located in South Boston near the Beach, Convention Center, Seaport District and Downtown Boston. Huge deck with views of city skyline. This home...

  8. APARTMENT
    506 on Parker Hill Apartment

    506 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

    $213 to $346/night

  9. APARTMENT
    306 on Parker Hill Apartment

    306 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

    $213 to $346/night

  10. 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

  11. 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

  12. 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

  13. 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

  14. 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....

  15. 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

  16. HOUSE
    75 Red Brook Rd Home

    75 Red Brook Rd Home

    East Falmouth, MA

    Enjoy the magnificent water views from inside or out. Beautiful gardens with a waterfall, gunite heated saltwater pool with spa, outdoor shower and pool house w/half bath make this home perfect for outdoor and indoor fun. Launch our 2 kayaks or...

    Pool Hot Tub
    FREE CANCELLATION

    $635 to $1,120/night

  17. HOUSE
    112 Ransom Home at Falmouth

    112 Ransom Home at Falmouth

    Falmouth, MA

    Sitting directly on Oyster Pond with a view of Vineyard Sound, tucked away on a private wooded peninsula, this 1930s summer home radiates charm and comfort with its own dock, two rowboats (with sails), a large canoe, and a kayak. Oyster Pond...

    Pets OK
    FREE CANCELLATION

    $309 to $596/night

  18. 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

  19. 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

  20. HOUSE
    75 Lake Home at Cotuit

    75 Lake Home at Cotuit

    Cotuit, MA

    A quintessential Cape Cod getaway awaits your crew of six 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

    $237 to $676/night

  21. HOUSE
    158 Long Beach Road Home

    158 Long Beach Road Home

    Centerville, MA

    Property Overview  Overlooking the Centerville River, this brand-new 3BR/1.5BA home affords an amazing location for your next Cape Cod getaway. Situated right on the water, an expansive deck provides a fantastic spot to relax, grill up dinner, and...

    FREE CANCELLATION

    $282 to $836/night

  22. HOUSE
    120 Boreen Home at Eastham

    120 Boreen Home at Eastham

    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 newly...

    FREE CANCELLATION

    $236 to $610/night

  23. 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

  24. 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

  25. APARTMENT
    Brookline Brownstone

    Brookline Brownstone

    Brookline, MA

    This 3 BR 2 BA apartment is fully updated and has in unit laundry. Good for couples, solo adventurers, traveling nurses, doctors, business travelers, families (with kids), and big groups. The apartment is minutes from Longwood Medical Area, home of...

    Pool Hot Tub Pets OK
    FREE CANCELLATION

    $294 to $541/night

  26. APARTMENT
    110 on Parker Hill

    110 on Parker Hill

    Boston, MA

    Mission Hill Apartment, 2 bedroom, 1.5 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 2018 and...

    Pets OK
    FREE CANCELLATION

    $227 to $392/night

  27. APARTMENT
    201 on Washington

    201 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
    FREE CANCELLATION

    $193 to $392/night

  28. HOUSE
    97 Pheasant Cove Cir Home

    97 Pheasant Cove Cir Home

    Yarmouth Port, MA

    Take in incredible, ever-changing marsh views from this traditional 4BR home (sleeps 8) in a quiet Yarmouth Port neighborhood. Enjoy the convenience of 2.5 bathrooms in addition to an oversized outdoor shower for rinsing off after the beach. A...

    FREE CANCELLATION

    $319 to $555/night

  29. HOUSE
    Classic Cape Cod House

    Classic Cape Cod House

    Truro, MA

    Water surrounds you at our 3BR/2BA classic Cape Cod vacation rental! Watch the sun rise and sink over two different bodies of water. At first light, bring your coffee to the home’s back deck and watch the sunrise on Pilgrim Lake, which is also...

    FREE CANCELLATION

    $206 to $472/night

  30. HOUSE
    Coastal/Beach Access Cottage in Centerville

    Coastal/Beach Access Cottage in Centerville

    Barnstable, MA

    Historic grandeur, quaint seaside energy and a friendly community bring visitors from near and far to the shores of Cape Cod. This renovated 3-bedroom, 1-bath cottage embodies the best of this town by the sea, on a lakefront property in a tranquil...

    FREE CANCELLATION

    $231 to $465/night