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. 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

  2. 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

  3. 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

  4. 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

  5. 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

  6. 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

  7. HOUSE
    62 Crowell Road Home

    62 Crowell Road Home

    East Falmouth, MA

    Set on three scenic acres beside the glittering waters of Bourne’s Pond, this 4 Bedroom / 2 Bathroom home offers a tranquil haven with fabulous sunrises, its own private beach, dock and a sunny screened-in porch. Feel like a day on the water?...

    Pets OK
    FREE CANCELLATION

    $170 to $625/night

  8. 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

  9. 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

    $193 to $620/night

  10. 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

  11. 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

  12. 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

  13. 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

  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
    361 Shore House at North Truro

    361 Shore House at North Truro

    North Truro, MA

    Picturesque water views await at this 3BR/2BA Beach Point home just across the street from Cape Cod Bay. Make the quick walk to the beach or take a short drive to the stunning National Seashore beaches. Provincetown is just 2 miles away, offering...

    Pets OK
    FREE CANCELLATION

    $392 to $690/night

  16. 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

    $257 to $740/night

  17. 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

    $245 to $445/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
    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

  20. 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

  21. 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....

  22. 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

  23. 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

  24. 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

  25. 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

    $227 to $1,046/night

  26. HOUSE
    16 Alden St Home at Provincetown

    16 Alden St Home at Provincetown

    Provincetown, MA

    Property Overview  Tucked away off a quiet residential street in the center of Provincetown, this 4BR/3BA home offers a peaceful retreat along with a convenient location -- just steps away from the pier, ferry, and all the charming boutique shops...

    Pets OK
    FREE CANCELLATION

    $482 to $1,042/night

  27. HOUSE
    312 Carriage Lane Home

    312 Carriage Lane Home

    Barnstable, MA

    With a quiet location in an historic Barnstable neighborhood, this 4 Bedroom / 2 Bathroom home offers a wonderful sense of seclusion, though countless local attractions sit right on your doorstep. Walk 1.2 miles to unique shops and restaurants...

    FREE CANCELLATION

    $162 to $571/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 $583/night

  29. HOUSE
    Cape Cod House at Truro 599

    Cape Cod House at Truro 599

    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

    $191 to $559/night

  30. 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