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
    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

  2. HOUSE
    112 Ocean Drive Home

    112 Ocean Drive Home

    West Hyannis Port, MA

    Climb to the roof deck on the third floor of your 3BR/3.5BA classic Cape retreat for a peek at idyllic water views. Decorated in classic Cape Cod style, this newly constructed rental provides the comfort and nostalgia of a traditional beachside...

    FREE CANCELLATION

    $597 to $946/night

  3. HOUSE
    Oceanside Hyannis Beach House

    Oceanside Hyannis Beach House

    Hyannis, MA

    This 4BR, 2BA Hyannis beach house sleeps 9. Relax on the deck with spectacular views of both sunrise and sunset, and watch the island ferries shuttling passengers to Nantucket and Martha’s Vineyard. You are a 3 minute walk from Kalmus Beach and...

    Hot Tub
    FREE CANCELLATION

    $166 to $780/night

  4. 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

  5. HOUSE
    22 Sunrise Lane Home

    22 Sunrise Lane Home

    Harwich, MA

    Completely renovated, this beautiful 4BR/2BA Harwich home features a welcoming open floor plan with high ceilings, hardwood floors, and central AC throughout. Whip up tasty dishes in the gourmet kitchen, relax in one of three living areas, or spend...

    FREE CANCELLATION

    $368 to $682/night

  6. 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

    $252 to $561/night

  7. 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

    $255 to $865/night

  8. HOUSE
    Countryside House 21

    Countryside House 21

    Harwich, MA

    Property Overview  Surrounded by well-tended landscape and lush gardens, this two-story 4BR/2BA home offers the ultimate home base to explore the Cape’s tranquil countryside. Beautiful hardwood floors and coastal-inspired decor are sprinkled...

    Hot Tub
    FREE CANCELLATION

    $135 to $475/night

  9. 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 $1,142/night

  10. 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

    $244 to $740/night

  11. 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

  12. 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

  13. 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....

  14. HOUSE
    Woodsy Cape Cod Home

    Woodsy Cape Cod Home

    Wellfleet, MA

    Get in touch with the wildlife of Cape Cod at this 3BR, 2.5BA home (sleeps 8) just across from a tidal creek flowing into Cape Cod Bay. Travel the gorgeous trails of the Audubon Sanctuary, or drive 20 minutes to Provincetown. The marshes are...

    FREE CANCELLATION

    $121 to $534/night

  15. 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

    $217 to $556/night

  16. 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

  17. 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

    $188 to $1,046/night

  18. HOUSE
    73 Sequat House at Harwich

    73 Sequat House at Harwich

    Harwich, MA

    Business : nearby atm, nearby post office, nearby internet cafe, nearby bank Living : central air, air conditioning, ceiling fans, linens, washer & dryer, ironing board, high speed internet, fireplace, iron, hair dryer, cable, dvd, games, heat Local...

    Pets OK
    FREE CANCELLATION

    $488 to $1,473/night

  19. 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

  20. HOUSE
    Serene Chatham House by Oyster Pond

    Serene Chatham House by Oyster Pond

    Chatham, MA

    The far reaches of Cape Cod are easily discovered from this quaint 3BR, 2BA house hidden in the woods. Just steps from Oyster Pond, our rental sleeps 6 and will delight any kayaker or fisherman. Spend evenings listening to the birds on the porch - a...

    FREE CANCELLATION

    $121 to $510/night

  21. HOUSE
    41 Quivet Home at Dennis

    41 Quivet Home at Dennis

    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

    $385 to $705/night

  22. HOUSE
    12 Bayberry Lane Home

    12 Bayberry Lane Home

    Eastham, MA

    Memorable beach trips begin at this elegant 2BR/3BA Eastham house. With a private master bedroom and separate family suite, there’s plenty of room to spread out. Watch the sun set over Cape Cod Bay from the upper deck, or follow the walking path...

    FREE CANCELLATION

    $829 to $1,174/night

  23. 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

    $300 to $577/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...

    $202 to $367/night

  25. DUPLEX
    460 Lower County Road Duplex Left Side Unit

    460 Lower County Road Duplex Left Side Unit

    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

    $106 to $260/night

  26. HOUSE
    63 Harbor Road House

    63 Harbor Road House

    Hyannis, MA

    This spacious 4BR/3BA 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 al fresco meals on the patio in the big fenced yard. Spend...

    FREE CANCELLATION

    $254 to $744/night

  27. 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

    $2,686 to $5,204/night

  28. 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....

    $1,511 to $3,189/night

  29. 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

  30. 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